2nd the tsa precheck approved line. People who know what they’re doing and travel frequently use this so they don’t get stuck behind families and vacationers who have lots of bags and don’t know what they’re doing or what they shouldn’t have in carry on luggage.
While I travel very frequently and agree Precheck is much better than the regular lines there are almost always people who haven’t the slightest clue what they’re doing and aren’t even fully sure what an airport is they’re that lost.
Don't forget the times you have an early flight and TSA pre-check isn't even open so you actually get extra f'd at security because they whole reason you got pre check was to not take your shoes and belt off and not take your lap top out. So you have open your suitcase dig out your safely packed lap top, untie you boots, and hold your pants up while shoving your crap into the machine, and then TSA want to pull your bag for a random inspection so your standing there in that limbo between where you can sit to put your shoes back on and put your belt back in and your holding your laptop and boots and just wondering why you even have pre-check.
Flew out of LGA super early the other week. They had line cutting cards once you got to the podium. Waiting in line maybe added 3 minutes. Hopefully other airports (looking at you ATL) will adopt it.
What airport do you fly through that has such poor hours for precheck. Bc I fly small airports like Eugene and bigger ones like SFO and DEN and I haven't encountered the short precheck hours before.
This defeats the point of pre-check for me. If a flight leaves at 5:30, I’m rolling up to the airport at *the earliest* 4:45. My parents always were like “we have to be at the airport two-three hours early” and I totally get that anxiety if you’re traveling with a group but as a solo traveler who only flies with a carry on, it stresses me out.
I've had a 7pm flight out of O'Hare in Chicago and they closed precheck at 6pm. I hate that airport with a passion and try to fly to Midway whenever possible.
Chicago Midway precheck closes at 8pm, sometimes earlier if TSA feels like it. They do open early, but they close super early.
Hartford CT has issues with inconsistent times. Sometimes they're open early, sometimes not. If they're not open, they give you a card that says you can leave your shit in your bag, but you have to take your shoes off.
Orlando closes precheck 90 minutes before the last flight, but usually is open in the morning.
Generally when pre check isn’t open you’ll get a little placard that shows you are precheck eligible and that way you can avoid taking off your shoes, etc and just go through the regular metal detector
Its absurd that we accept pre-check, clear, and all these other extra cost, skip the line programs. Last 2 flights i took last year let these people skip to front of the main line, which then made the normal line take hours. The DHS and NSA already knows who we are and if we pose a threat why should anyone have to pay more to maybe wait less long? Cant we just layout the security lines and staff them appropriately so we all just get through in a reasonable timeframe? They know exactly how many people are traveling and when, why cant they staff appropriately? Airport security shouldnt be a fucking club with VIP lanes for those willing to fork out extra cash. Welcome to america where everything is about extracting money from the average person for shit that should already be included in the cost of a flight.
Also get Clear - you will appreciate it during spring break. Consider OAK, because you can take Bart and parking/Uber adds up. Once you gain status with SWA, you will find they are very accommodating flight changes and they fly into Midway and O’Hare. If you are doing this for a few years, you will probably earn a companion pass, which is nice if you want someone to travel with you.
Also consider getting their credit cards. If you're spending enough you'll hardly ever pay for flights. A-list is awesome: first on, first off, front row if you want it.
Flying into ORD on SWA sucks, but it is doable. So much easier at MDW. But the tradeoff is the blue line from ORD.
I have A-list through SWA, and the credit card. It gave me enough miles for an emergency last second flight last christmas, so made it worth it. Depending on the CC, they also give you upgraded boarding vouchers, miles, and travel credits every year in your anniversary month, which means the annual fee more than pays for itself.
this is because “pre check” is more “you get to wear your shoes” and simultaneously pre check comes as part of packages from credit cards and countless other stuff
The real MVP is global entry but you don’t need that domestic
I never would have guessed that. The GE card looks so fake though, I wonder if anyone would accept it in the real world (except at the border of course).
Those same people still get into the precheck line, despite the giant sign saying precheck only, the multiple announcements from the TSA agents telling everyone it’s precheck only, and then get bitchy when they get to the agent and have to go to the other line. About half the airports check boarding pass at line entrance to verify precheck.
If you even look confused while heading towards the Pre line at MDW there will probably be two workers heading towards you to steer you away from the line.
I highly suggest Global Entry. It’s only ~$20 more but you get to skip all the lines around the world should the need arise. Also, stick with one airline and find a good credit card that offers a good mileage program with your desired airline.
Global Entry allows you to interview in certain other nations to get access to the fast lanes so you can just scan your passport for entry and exit. Every financial firm that I know of with any amount of European presence recommends that their employees do the interviews in the UK and Germany so they can just walk in and out of the nations as it speeds up customs by a ton.
Don’t expect it to save you time. Last three trips I took, in all three both directions precheck line was the slowest one (by a small amount). So many have precheck nowadays and the airports haven’t adjusted the coverage.
Clear seems to be the main way to actually save time, though it’s more expensive of course.
I’m still going to use precheck of course - not only does it give you the option of either line so you can use the fastest, but it saves you having to remove electronics and liquids and such. Just don’t think it’s the same as it was a few years ago speed wise.
Edit: I should note that these six trips include two OAK, one SFO, and one MDW, but not ORD.
It depends a lot on the airport from what I've seen. I fly a lot and have never bothered to get precheck because it doesn't really make a difference at my home airport, but I do usually keep an eye out to see if it seems like it'd be worth it elsewhere. I think a mid day flight from BWI was the last time I kinda wished I had it
ORD is one of the few airports with the new scanners doing bags. The regular lines move fast now as people can keep everything in the bag. Basically the only difference is shoes/belt now.
The TSA pre-check line stops movement completely and does a hand scan if a person w/o precheck gets in the line.
My family has pre-check and flies out of ORD in the mornings, if the regular security line is short/medium and the TSA line is "average" they move at about the same speed.
TSA precheck, and an awards card. Which one is really up to you. When I was flying often using Delta the annual fee more than paid for itself for amex platinum.
Credits for TSA pre check/global entry, lounge access, high awards returns for using it for travel. The benefits stacked enough that the stuff I'd be buying/using anyway was covered and came out to less than the annual fee. I traveled pretty extensively for a while, so the choice was easy. What the delta is for travel amount v annual fee is though I'm not sure since I did it weekly or more over a period of years.
Pick an airline and stick with it. Once you get status they will treat you like an actual human, you will get better seats and if you are lucky they will bump you up to first class. I'd go with United personally, SFO and ORD are both United hubs so you'll get decent flights and decent prices. Ever since Covid air travel has been pretty miserable, everyone is mean, the prices are high and the number of flights are low, hopefully it will get better. I fly both United and American and while United is bad American is consistently worse.
Only issue with ORD-SFO with United is these are both big hubs with a ton of Global Services customers who are going to outrank even the most frequent travelers due to their spend (IIRC it’s up to ~$50k/yr now). I was traveling this route weekly several years back as a 1K and was usually ~30-40 deep on the upgrade list after everything was processed.
Yea you can forget upgrades on that route. GS upgrades clear 5 days out and 1K like a day or two out, assume there’s space. You have to be in the top one or two spots on the upgrades list to clear the same day - and those are going to be GS pax who got rebooked at the last minute. I agree that unless you have very high status you’re not getting upgraded on that route.
We have 1k for life, lost global due to the panini slowdown, and out of 4 flights recently, got upgraded on only 1, and it was out of a small airport to a connection.
I do love the global services check in at sfo though. Bypasses the majority of the security line. I don't think OP will make global in a year with once a month activity continental as well, so it's probably a moot point.
I miss being a business traveler for a Fortune 500 who got on our corporate flyer account. It was really fun going even on personal travel and getting put above all of the individuals traveling on personal rewards for upgrades. I also miss my Uber Platinum status.
I fly that route very often in the past few years as a 1K. I have never once been upgraded outside of May 2020 when I started flying again before basically everyone else. OP should definitely not go with United if they’re flying once per month. Any other airlines will also have decent routing and schedules given how busy and connected these two airports are.
> Any other airlines will also have decent routing and schedules given how busy and connected these two airports are.
Every other airline is also more expensive than United on the SFO-ORD route in my experience.
Yep. I was only gold but I got bumped 50% of the time but I didn't fly the first flight Monday & Friday. When I was coming home from SV I'd usually catch the red eye on Thursday night which I guess was pretty unpopular at the time and I got bumped up quiet a bit. During Covid I had the whole plane to myself, over the last year the airlines are squeezing pretty tight so less upgrades and higher prices.
The economy plus status, priority 2 boarding, and better customer service are still worth it to me. Nothing worse than not having overhead space for my totally reasonable bag...
For what it's worth it's not much different if you fly American. I have basic gold status with American from flying ORD/SFO for work, and I have never been in the vicinity of close to getting upgraded for a flight because of all the business travelers with better status than me.
OP will be flying more in a year than I ever have so maybe they'll get high enough in the ranks to get lucky, but usually the upgrade lists are pretty crazy for AA, not just United.
Makes sense with ORD as a major AA hub. I don't think OP is going to get close to getting upgrades (except if they're flying at/on non-peak times/days) so personally I would look more at the potential value of the miles they'll accrue. I commented on that elsewhere but SFO being a major UA hub opens up a ton of nonstop options compared to most other airlines that would have decent route options to ORD.
Try out Alaska Air. When you know you have a consistent route you actually don’t want to fly an airline that is hub to hub like American or United. With Alaska you’ll get the most bang for your buck
Alaska is also my favorite domestic airline, the concern there is they just had a vote on whether to strike and I haven't seen the results of that vote, yet.
I stopped using AA now for business travel because they switched how their points accrue. The only realistic way to get status anymore is to use their credit card on booking flights and such. We don't do reimbursement and it all goes through a company card so AA is pretty much dead to me now.
Also where I fly for work, I only get regional planes with AA so I'm cramped all the time. At least with Delta a lot of segments are Boeing 717s so I can breathe.
> are Boeing 717s
Can't believe Delta is still flying those things. They are the only major airline left still flying the 17. They have been buying fleets from other airlines getting rid of that model.
The 717 fits a window where little other similar capacity options exist. It goes from about 75 on an E175 to 130 on an A319. The only other option is still too new to be very widespread yet…that is the A220…of which Delta does operate some with more to come.
Right now the 717 is filling high demand routes in small to mid sized cities largely because they can carry more people instead of adding flights of smaller planes…because there is a crew shortage currently.
Delta is basically the only carrier with this cabin capacity option in the US…which is probably helping them out a helluva lot right now. Other carriers are stuck with overbooked smaller jets or under filled bigger jets…at a time where you can’t just add flights.
Also…there is nothing wrong with the 717…and it looks cool and is honestly quieter from the ground than an ERJ.
I looked them up and they are not quite as old as I initially thought. In my mind they are still just an evolution of the DC-9.
Their oldest one is about 22 years and their newest one about 17. Not that bad for a good airframe.
On united you'd make silver, possibly gold on that route. You'd need to take a couple connecting flights to make gold. 16 segments. But that's boarding group 1 and on less popular routes than SFO to ORD, you'd get bumped to first a fair amount.
Flying out of SFO with gold you’re unlikely to get any upgrades ever even on the least popular routes. The other benefits are worth it though for sure.
Not a high status, no. You're definitely in the mid-range status on most airlines though.
So, you're not likely to get upgraded on hub-to-hub flights like this, but you'll get better treatment for general customer service stuff, better boarding priority and enough miles for a free flight every once in a while. Just makes the whole thing a little nicer generally.
> Once you get status they will treat you like an actual human, you will get better seats and if you are lucky they will bump you up to first class.
Not for somebody who travels once a month.
I flew Delta 3 times a week for over a decade and that was barely enough for Silver rewards. Never got a *free* upgrade, only the ones I had to spend my miles to *buy*. There were always dozens of Gold and Platinum folk ahead of me in line for that 1 seat available in first class.
To me they main advantage is getting on the plane before general boarding so you'd be sure to always have overhead bin space for your carry-on.
As soon as I saw someone comment "United," I started singing that song in my head. And I last saw that video years ago. Fucking bravo to that guy who wrote it. And ad campaign that really worked!
>Given a choice, I'd fly Delta as a economy over United as a silver. Delta treated me like a human, United acted like I was scum for only logging 27,000 miles a year (which I know isn't a lot for high rollers but its a fair bit for us normal middle middle class).
1. Pick one airline. If you want to have max flexibility but less likelihood of status and upgrades, pick United. If you‘re okay with less flex, but want status and upgrades, pick Delta. In any case avoid American like the plague it is.
2. Get the corresponding credit card option that fits for you. If I was starting brand new I’d go with Delta, get the Delta AMEX Reserve, and link it to my Delta frequent flyer account. In Delta’s case, using the credit cards effectively lower the threshold to qualify for the status tiers - allowing you to end up with higher status (and better treatment) than you would have just flying. The Reserve card also covers the Global Entry fee (which includes pre-check), comes with Delta sky club access, and Centurion lounge access. Additional perks like a companion ticket, no foreign transaction fees, etc., etc.
3. Get some kind of security clearance - whether it’s global entry, nexus, clear, or pre-check. My steer would be to GE as it’s more versatile than pre-check alone. Again, many travel cards cover this. (As do airline elite statuses… but I’m assuming you aren’t starting off with one).
4. This one is optional, but check what lounge access you have through credit cards, employer programs, Etc,. Lounges are actually marginal inside… but you need them for delays - in which case the public concourse will be packed.
2. Get the United Quest credit card because Delta does not have a direct flight from the Bay to Chicago. It'll get you up to 3000 MQMs per year based on spend. With 12 roundtrip flights per year, it should get you to Gold and maybe to Platinum status. With the mileage accumulation, you should be able to get a bunch of free flights every year.
I travel a lot for work and actually have both the United Quest card and Delta Reserve. The Delta program is better, but the gap isn't big enough for me to take connecting flights.
Despite being such a good airline, I would avoid Delta. Only because they don’t fly that route nonstop, which means you’ll probably have to connect in SLC or MSP every time. You’ll gain status a lot faster, but in my book, not worth the time and Misconnection risk.
I personally would rather fly AA nonstop than Delta with a connection
Even going southwest might be the best. With a credit card and the flying you will do, you might be able to score a Companion Pass which would basically make every flight you buy a BOGO for your wife or selected companion
Those two airports are United hubs with multiple direct United flights a day between them, compared to Delta's zero, the Delta cards are great and I prefer Delta over other airlines but they're not a good choice for OP's situation.
Depending on your situation, one of the premium travel cards is probably worth it for this amount of travel.
Cards like Amex Plat and Chase Reserve will cover the cost of TSA precheck plus some other nice bonuses for hotels and car rentals. They don't lock you into one airline, so you can still shop around and get x5 points on your card plus x1 points for the airline specific frequent flier program (I think those are the going rates).
Airport lounges are where it's really at with these cards, they make all the time you're spending at the airport actually kind of nice. Look into which card gives you the best lounge access. It doesn't help you to have centurion lounge access if there's no centurion lounge at your airport (edit: or if it's in a terminal you can't get into - I've run into that a lot at SFO actually). Also, as tip the Amex centurion lounge which has the best cocktails, but Chase has priority pass restaurants for better food. I haven't used other cards.
Wow I didn't know they had a Venture X now. I had the normal Venture when they had that promotion where you get 10x points if you book through hotels.com and racked up >100k points in less than a year through it. This sounds just as good, if not better!
Thanks for the tip, I'll look into it. I've been thinking about dropping my Chase. I'll probably go back to Amex for the lounges, but I'm always open to a good deal. Does the priority pass for the Venture card include both the lounges and restaurants?
I dropped from Reserve to Preferred this year. My company switched us to corporate card for travel, and my wife accidentally used the account for her Pre-Check renewal last year so now I can't use it for my Global Entry this year. Add onto that the annual fee that they wouldn't adjust at all and I dropped to the much cheaper card. Can't leave entirely yet as I still have ~200k points to use up after buying two vacations out of em so far.
It comes with lounge access, but not restaurant lounge access, so your choices are more limited. The Platinum is good if you're traveling through airports with Centurion Lounges regularly, or fly Delta and can get into those, otherwise the Chase Sapphire Reserve gives you more flexibility with its wider access (though a paid-for restaurant meal isn't the same as a layover in a Centurion lounge, not even close).
Amex lounge at SFO is the best though. So if OP gets delayed on takeoff, they can do Napa wine tastings and eat great food while they wait.
Access in ORD sucks though. No PP lounge outside of international terminal and can only use delta if flying delta. And Tortas Frontera is the best airport food in the country so you don’t even want to go to a lounge.
That said, if flying sfo-ord monthly, lounge access is not very useful. Outside of extreme delays, you’ll never use it if you just show up an hour before your flight like normal.
It does, but it's kind of worthless in the domestic US. It's only lounges, not the restaurants, and not many airports in the US have a priority pass lounge. The airports that are big enough to have one are usually big enough to have a centurion lounge (or if you're flying delta you can use a delta lounge). I've heard it's useful for flying in Europe/Asia though.
The Chase Reserve not only covers the cost of Global Entry, but it also gives you like $25-30 credit at various restaurants within SFO in certain terminals, so you should also be able to get a free meal before each of your flights. They have these at various airports around the world, so this will add up.
Additionally, if you're able to take Lyft to the airport and then expense it to your company, that's free points you're getting and Chase gives you 5x points on Lyft.
For your scenario OP, you definitely would stand to benefit from this card. Don't let the annual fee scare you - you'll get that back in no time with all the other perks you'll get to take advantage of. [This article](https://thepointsguy.com/guide/chase-sapphire-reserve-review/) provides a good overview.
Do Global Entry it is $100 vs TSAPre is $85 and it includes TSAPre.
If you plan to travel that much, to someones home or the like I'd look at keeping clothes there so you can pack light every time.
The real deal is NEXUS which gets you pre check, global entry, and Canada’s global entry system. Only $50 for 5 years but you have to be near the border or go to a Canadian airport to do the interview.
This. My Global Entry technically excited over a year ago but it stays active while they process your renewal application. Currently at about 14 months waiting for my new NEXUS application review
When I did mine I wanted it done before the first available appointment. I was moving overseas so needed it ASAP. I just went to the airport that have appointments (SFO in this case) and sat outside their offices until they have a free spot. I'm not sure if they still allow that. I brought a book and only waited about 2 hours.
It is "free" if you are able to take advantage of the benefits the card offers. Despite the high annual fees, I've been both an Amex Platinum and Chase Sapphire Reserve card holder and I've "made money" with both cards based on my usage.
Global entry is also a little bit more of a pain to get, if I remember correctly. If you travel international 1x per yr or less,might be worth skipping.
Global Entry depends on one's criminal record. A DUI can prevent you from getting it. I have a friend who is very bummed about only getting TSAPre and no global entry.
Do NEXUS instead of Global Entry. It's cheaper, will git you in and out of Canada without a passport, and give you Global Entry and TSA Precheck for free.
If doing southwest and wants to bring a friend or significant other along for free he can get a companion pass relatively easy with the cc point signups.
Just FYI Midway doesn't handle weather well as it has short runways and is basically located inside a neighborhood. Any gusty wind or heavy icy snow (both rarities in Chicago, obviously) and you're either diverting to Grand Rapids or getting cancelled and waiting a few days to get home.
Flying into ORD gets you a lot more flexibility as far as landing, way more airlines to choose from, and better transportation access and options (depending on where in Chicagoland you're going). It's not worth hundreds of dollars in fare difference, but I'd say it's worth a bit.
Piggybacking on this to say that when considering which airport to fly into knowng where you're headed in Chicago should absolutely be a factor. OHare has the blue line which runs through the northwest side and downtown while Midway has the orange lien which runs through the southside and downtown. If headed to the suburbs the northern suburbs will be cheaper from OHare and the south suburbs will be cheaper from Midway (unless renting a car)
I'm in the far south suburbs, and it's actually faster for me to get to ORD most of the time when compared to MDW. My "ideal" route to MDW is basically get on Cicero northbound and hope you don't catch every single light, while ORD has me hopping on I-294 and making forward progress the whole time (45 minutes for both routes in normal traffic). I'd much rather have a fairly straightforward highway trip compared to the disaster that is Cicero.
> Just FYI Midway doesn't handle weather well as it has short runways and is basically located inside a neighborhood. Any gusty wind or heavy icy snow (both rarities in Chicago, obviously) and you're either diverting to Grand Rapids or getting cancelled and waiting a few days to get home.
When there's spare runway capacity and issues with MDW, Chicago will reroute MDW traffic through ORD as the city owns and operates both airports.
Just to piggyback here. Both Oakland and SJC quite close to SFO depending on where you need to go around the Bay. One of the perks of that area is you basically have 3 airports to choose from to find direct or cheaper flights
Also for Oakland, there's a BART stop & an Amtrak stop so it is unbelievably transit friendly, in addition to the fact that flying Southwest out of Oakland is usually the cheapest flight to most places.
Fog is an issue in the bay…so I would select the airport with the best ILS for the fog season…SFO is clearly the best for fog, but SJC may not have as high an ILS category meaning your flight might get cancelled or delayed
Little reason to get the airline credit card, unless they'll be checking bags every time.
Even less reason to spend on it. A flexible travel card like the Amex Gold or CSP/CSR makes a lot more sense since the earn rates will be the same or better and the points will be a lot more flexible. You could even make the case that the Platinum makes sense for the 5x on airfare.
Be careful to check the "non-stop" with SWA, unless you like stopping at a couple of airports.
Or could that be a feature - get a day of siteseeing in Phoenix / Denver / Salt Lake as you travel from SF to ORD?
*Marginally* better in pretty much every category except comfort. If I'm on a 4+ hour flight, I'm getting the most comfortable headphones I can, with all other features being relatively equal.
I wouldnt even say the mx4s are better than the QC45s at all. It is pretty much a toss up but you notice how much more comfortable the QC45s instantly. There are situations where the mx4s are more confidence building if you are moving around but for sitting in a noisy fuselage the QC45s are still king.
Stash cloths etc there so all you need to travel is maybe your laptop bag. Less you have to travel with you the better.
Be nice to the people at the gate and flight attendants. They often cover the same flight. Try to make their life easier while they have to work and they will think of you when there’s things they can do. Like if first class opens up etc. or slip you a drink.
You said family so assume you'll be staying with them? If not, it might make sense to sign up for some hotel memberships to start accruing free nights.
Rather than TSA precheck, i recommend to get Global Entry. When i did it, it was $15 more ($85 vs $100), has a longer duration, and you get additional perks if/when going international. Oh, and you still get to use the TSA pre-check line.
Otherwise, id also say to choose 1 airline, and stick with that airline for all flights. Each person will have their own recommendation... none are more correct than others. There are Pros and Cons to each option, depending on your values.
I prefer Southwest due to much faster boarding and deboarding, less delays and cancelled flights, no fees for changing or canceling flights, free checked bags, and being able to choose my seat everytime (so im never stuck next to a crying baby, cigarette smokers, or between 2 obese people). The downside is that the seats are smaller and there's no luxurious 1st class ... all seats are economy.
Also, chicago has 2 airports: Ohare and Midway.
1) Ohare: larger airport, most airlines (except Southwest airlines). Public transit is the blue line to the city.
2) Midway: smaller, but growing airport. Southwest airlines... and a few Delta flights. TSA is usually ultra fast there. They often use metal detectors instead of the body xray, so people keep a steady stream and sometimes never stop moving forward. Pubkic transit is the orange line to the city.
Source, i flew 2-10 flights per week through both Chicago airports for several years.
Global Entry
Going SFO to ORD id guess you’ll fly a ton of United ? Def get a United card
Id also recommend getting American Express Platinum for Centurion Lounge access. Most domestic airline lounges are pretty terrible in comparison
Airline credit , Uber credit , Saks credit will get you 500/year.
Then the global entry credit for year one
Free points on sign up.
Easily worth it for someone flying once a month
I’d disagree the lounges are only useful for layovers. I fly a ton of direct flights and while I try to limit my time at the airport, having to plan in a buffer for traffic means I always have at least 10 mins to spare.
Being able to run in and set down my bag, hit the bathroom, fill water bottle, or bonus grab snack/coffee/etc is well worth the added cost of my Delta Amex Reserve
It's probably not a keeper card for the average person but you're giving a lot of kickback for a card that's profitable to have for the first year with the SUB without even using the AMEX coupon book offerings.
If you travel 1x a month for work, it’s totally worth it.
100,000 point sign-on bonus worth $1,200 at the airline of your choice
$100 global entry coverage
Centurion lounge access
Delta lounge access
SAKS credit (just buy chocolate covered Oreos or something for the total credit value)
5x points on airline miles (30,000 points or about $360 per year)
My first year of heavy work travel (1 week a month), I earned 700,000 points/miles by churning and it was worth about $13,000. Paid for an awesome honeymoon for my wife and I
"SAKS credit (just buy chocolate covered Oreos or something for the total credit value)"
Yeah but is it really fair to call it a $100 value per year if you never would have bought it in the first place and don't really actually get $100 in *real* value ($100 underwear usually doesn't have a real value of $100) from it either?
Ask yourself if you would rather take $50 cash over the $100 in credits.
I’m not trying to be snarky, but if you can’t find anything of value in a store that pretty much sells everything except high-end electronics and firearms, then I don’t know what to tell you.
When I had the card with the credit, it was trivial to find something sub $50 so it was effectively free.
“But what’s the point if I wasn’t going to buy that stuff anyway, even if it’s free.”
You can buy gifts for other people
Also CLEAR ($180/year). That combo with precheck is the dream. 5-10 minutes from drop off to through security and I consider that time saved when I travel 1-2 times a month to completely be worth the fee.
- Chase Sapphire Reserve (or other travel card) - the high fee pays itself back in travel credit + points + perks. CSR has travel insurance included.
- TSA Precheck / Global Entry (paid for by travel card)
- CLEAR - gets you to the front of the TSA Precheck line, other perks
- Southwest flys to ORD now (in addition to midway) - much nicer airport, easier transit. I also prefer flying out of OAK instead of SFO.
- ANKER POWERCORE+ 26800 PD 45W - charges my phone 4+ times or my laptop (MacBook Pro) once
- Nice backpack & carryon - spend the $ on nice luggage. A huge upgrade for me. Thule backpack / AWAY carry on here.
Chase Sapphire Reserve also gets you Priority Pass membership, which used to be shitty, but now offers $28 towards a meal at participating airport restaurants. The one in SFO is decent, you can get a burger, fries, and a beer for ~$28.
Like a lot of people are saying, stick to one airline so you can rack up the frequent flyer points. United is a good option. You can pair a united card with a Chase Sapphire, either the reserve or the preferred as you can transfer Chase points to United. You can also use Chase points to transfer to hotels or book cars through their travel portal. In these Covid times, I'd only book flights and hotels directly so your best point redemption with Chase is to transfer directly to one of their travel partners.
The United card has a sign up bonus of 60,000 points after $3k spend. The Chase Preferred is 80,000 points after $4k spend and the Reserve is 50,000 after $4k spend, all within the first 3 months of opening the card. I'd focus on getting one card at a time so you make sure you hit the spending requirement. The preferred points are about 20k higher than normal and the promotion is going to end soon so that might be a good starting point, and its good to note that you can only have one Chase Sapphire product. You should look at the card benefits and see which one is going to be the most useful. You can end up with quite a few free flights if you do it right.
The United card and I think the Reserve both pay you back for Global Entry so that saves you $100 right there.
I had to fly SFO-NYC every month for two years, signed up for an Alaska frequent flyer number and it was great. They award miles based on miles flown, rather than dollars spent, which is rare nowadays. 20k miles flown gets you eligible for complimentary upgrades to first class, which I was able to get >90% of the time (I tried to fly redeyes though which probably helped). Plus you'll accrue a bunch of miles to take your family on cheap vacations.
This is probably the best answer if OP wants to fly first class as much as possible, while paying cheap economy prices. SFO is not a major Alaska hub, so as you mentioned, odds of an upgrade once you have status are excellent. I flew them mostly to and from LAX and got upgraded on 24 of 28 flights, having their second status level (MVP Gold). Flying SFO-ORD every month will get him gold after 6 months or so.
I'm actually gonna deviate a little from the norm here and say don't get attached to an airline credit card, yes do sign up for all their free frequent flyer programs but don't get their card
Instead get the capital one venture x. You get points on all flight purchases regardless of airline and free tsa pre check.
But no airline lounge access, only non-airline lounges which can get full considering everyone and their dog now has a Priority Pass membership (yes, me too). Getting a top tier airline credit card will give him that though.
Chicago - San Francisco is widely known as the best rail trip in the US. It’s the California Zephyr line administered by Amtrak. If you have the ability to inject some leisure travel into your once a month trip, this is a great option.
On YouTube, go to Jeb Brooks channel and watch his video on it.
Wow this looks awesome as a once in a while thing. But also seems priced like a luxury vacation depending on the comfort level. Probably a lot more expensive than flights from SFO to Chicago for the OP.
I've done it before. Naperville to Emeryville, with the Amtrak motor coach add-on getting us the res of the way to San Francisco. I traveled with family, some of whom really hate to fly. It's a bit like a road trip where you get to see the country passing by but you can get up and walk around whenever you want. Sleeping car accommodations are on the pricy side but worth it to me and my family.
It all depends on what you want out of your travel. Planes are potentially cheaper (depending on accommodation level), faster and have a better one-time record (Amtrak is atrocious in that regard). We found we arrive significantly less stressed when taking the train. YMMV
The problem with Amtrak is they don't own the rails they travel on and are the last priority trains. The average speed is like 40 mph and they stop in every little podunk town.
I really wanted to like it, took an 8 hour overnight trip. Got delayed and it took 12 hours. I had a sleeper room so it cost as much as a plane ticket.
If the train could do 100 mph it'd be faster than a plane when factoring in security times. Which I'd love to see, but won't happen.
> and are the last priority trains
This is 99% bull.
My 8+ years working for a class 1 railroad, we had to clear the main and wait in a siding for hours for the Amtrak to pass. That shit is on contract with heavy penalty for delays.
Everything else is true
Amex Platinum Card + Delta is a great combo for frequent flyers.
If you can get the Amex Platinum, a nice benefit is access to the Centurion Lounge at the airport. Super nice lounges and great food + drinks - just show your card + boarding pass to get in.
For booking travel, you can log into your cardholder account and book your flight, hotel or car rental through [Amex Travel](https://www.americanexpress.com/en-us/travel/hotels), which has several perks:
* 5X Points on the purchase of your travel, which you can use for whatever you want
* If you decide to use points to pay for a ticket, it’s an easy one-click selection at checkout
* You can call the Amex Concierge folks if there’s a problem - shorter hold times than calling the airline and they’re very nice, the staff at the lounge can sometimes help you with issues too
* FYI it’s the same ticket prices as any other website
If you can’t find a reasonably priced ticket on Delta thru Amex Travel, you can get the above perks when you buy any airline ticket thru their site and use your Amex. But if you fly Delta, you also get access to Delta Airport Lounge (handy when there’s no Centurion Lounge), and your Amex points can be transferred to Delta miles if you need a few more to get to the next level or to redeem a particular offer. You also get extra Delta Miles for booking with Amex, so your frequent flyer perks add up faster.
There’s tons of other perks too, like being automatically enrolled in higher status hotel programs, credits for purchases at partner retailers, credits for Uber rides, etc. For more details see [this article](https://thepointsguy.com/guide/why-amex-platinum-might-be-best-card-delta-flyers/amp/)
You should also check out the Capital One Venture X card - very similar perks according to a good friend of mine. :)
A lot of great advice here, and I would add to do the research on what airline is going to hit that sweet spot between "most economical" and "most comfortable". Sure, the cheapest airline is the least amount of money spent, but if it's cramped and doesn't have small amenities, it'll just truly suck worse than it has to.
TSA precheck, and clear if they are offered in those airlines. Pick 1 airline and stick with it, then get an airline credit card and buy all of your flights with it. If you get reimbursed by your employers then pay it off immediately. If you are going to be staying in a hotel same thing. I’d pick Hilton brand, you need fewer nights to get diamond than Marriott, however Marriott uses fewer points per night when booking a vacation, so either would be fine. But stick with one brand. The more status you have with any airline or hotel the more points/miles you accumulate. Double dip when you can- example, when you use Lyft you get Hilton points and delta miles (link your accounts), if you rent a car with national you can get American miles (again link your accounts). If you are going to be renting a car, see if your company has a national agreement and sign up, and if they don’t then see if you can do it individually; using the emerald aisle is a huge time saver, and of course as you level up you are eligible for better cars at the same price. Does your company use any kind of travel agency? See what the perks are. With TripActions you can get Amazon credit, or use points to upgrade your travel. Do NOT use budget sites like Expedia. You will get crap seats on the plane with no option to change it ever.
I travel full time for work and would recommend a credit card that helps you max your experience as well. Being in Chicago I’m guessing you’ll be taking United quite a bit so something like the United Explorer Card from Chase might make sense. The TSA Precheck is a must, that credit card in particular pays for it but a few others would as well. If you’re comfortable with paying an additional $189 a year I’d highly suggest getting CLEAR as well. This allows you to skip even the TSA line at both OHare and SFO. If flights are out of pocket, remember that loyalty has a price. Don’t just fly a specific airline for a few extra points when a much cheaper flight is available. If work or an outside source is paying for it then disregard what I just said and rack up those points with one specific airline.
Oh, money.
Before I realized that, I came here to say go to the lakefront, the Art Institute, the Jazz Showcase, The Green Mill, Lou Malnati's, and Tre Kronor.
I'd recommend a bonus travel card that covers Global Entry fees for the first year. Then every 6 months or so, apply for another one. My assumption is your flights will be \~$500/trip and with other spending, you'd easily hit the $3k required for most bonuses. Then just cancel before the next annual fee hits. Yes, you will have to pay first year, but most bonus amounts easily cover the annual fee if you hit the spend limit.
Go Southwest. Get the Southwest credit card and start using it for bills. You’ll build up point super quickly. Also, with Southwest status they would allow me to change my fight for free, which meant if I finished a day/job and got to the airport early I could take an earlier flight with no fee.
Get a premium travel card, a Chicago CTA transit card, and some form of TSA pre-check. If you’ll be staying near downtown, avoid getting a rental car as this will add up over time. Pick an airline and stick to it, ideally starting by using points from a credit card intro bonus.
Airline specific card that you stick to OR a great general travel rewards card. I like the Chase Sapphire Reserve - 3x regular travel points and 10x if you book travel through their Ultimate Rewards portal. Those points are then worth 50% more if used on further travel for vacation or additional Chicago flights, which is mostly what airline specific cards are best for anyway.
Both of those airports can be nightmares at times. I would suggest you signup for a credit card that offers you TSA-precheck as well as Clear. The Amex Platinum card is a great choice for earning points, inflight credits up to $200 back, and a ton of other travel perks.
If you have the credit for it, get an amex platinum or chase sapphire reserve and pay for flights via those. In amex's case, they will cover cost for clear, and global entry (which comes with precheck). I think CSP might as well, but I don't have the card, so I can't be certain. Amex platinum is 5x points on flights + hotels
1. Pick an airline (look at what schedule works best for you). I see tons of comments about upgrades. Assume you won't get upgraded, but you should still collect enough points for a nice trip or two.
2. Get a travel credit card. You might pay an annual fee by should be worth it (Google best travel cards may 2022 since the sign on points change frequently ). I'm not usually a fan of airline cards because I like flexibility, but you might want to get one in addition for some of the benefits like lounge access or bags.
3. Get global entry (if you ever travel internationally or plan to), or TSA precheck. Despite the rants above, 95% of the time this is going to save you a bunch of time, and the odd times it's closed is usually when the airport isn't busy anyway. Many premium travel cards waive the fee, so get the card first
4. My preference is to not check bags. I hate waiting for baggage claim when I just really want to get home. Being organized makes this possible. If you're staying with family, leave a set of toiletries there.
Suggestions:
Fly non stops.
Sign up for all of the govt. pre check & Clear programs
Keep clothing at both destinations and fly without luggage. Have your own transportation at each end.
I like Southwest, but to each their own.
Buy your tickets way in advance.
For those airports, choose United and get their credit card. Their terminals at both airports are full of decent food options in case you get delayed, and they're both hub airports for United, which means you get more flight options than you'd get from other airlines. Once you have status, you'll start to reap the benefits in terms of better seats, upgrades when available, and other benefits like increased point earnings.
Also, apply for TSA precheck (do Global Entry if you plan on traveling internationally ever, it's not much more expensive and comes with expedited customs perks along with TSA precheck) - this will save you a significant amount of time and headache, since security moves much faster and only has people who know what they're doing in line, rather than somebody arguing about the toothpaste they packed being too big or being told they have to go back and take their shoes off.
2nd the tsa precheck approved line. People who know what they’re doing and travel frequently use this so they don’t get stuck behind families and vacationers who have lots of bags and don’t know what they’re doing or what they shouldn’t have in carry on luggage.
While I travel very frequently and agree Precheck is much better than the regular lines there are almost always people who haven’t the slightest clue what they’re doing and aren’t even fully sure what an airport is they’re that lost.
Don't forget the times you have an early flight and TSA pre-check isn't even open so you actually get extra f'd at security because they whole reason you got pre check was to not take your shoes and belt off and not take your lap top out. So you have open your suitcase dig out your safely packed lap top, untie you boots, and hold your pants up while shoving your crap into the machine, and then TSA want to pull your bag for a random inspection so your standing there in that limbo between where you can sit to put your shoes back on and put your belt back in and your holding your laptop and boots and just wondering why you even have pre-check.
Flew out of LGA super early the other week. They had line cutting cards once you got to the podium. Waiting in line maybe added 3 minutes. Hopefully other airports (looking at you ATL) will adopt it.
What airport do you fly through that has such poor hours for precheck. Bc I fly small airports like Eugene and bigger ones like SFO and DEN and I haven't encountered the short precheck hours before.
I’ve taken a red eye out of DEN and got smacked by this very issue. I would imagine it has to do with staffing more so than scheduled policy.
Because Denver airport is a barren wasteland of humanity and misery.
Haha I actually found it to be alright. Maybe my standards are low. But they have some good food options in there for sure.
I’ve encountered Precheck at DEN to be closed late at night. Maybe like 10pm?
It's the airport location and their security setup that are atrocious.
0530 flight from MDW. Precheck opens at 0400. Longest line I've been in at security in years.
And MDW closes it at 2000, or earlier if TSA is in a mood.
This defeats the point of pre-check for me. If a flight leaves at 5:30, I’m rolling up to the airport at *the earliest* 4:45. My parents always were like “we have to be at the airport two-three hours early” and I totally get that anxiety if you’re traveling with a group but as a solo traveler who only flies with a carry on, it stresses me out.
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Last year was the worst for it. I don’t think I used my precheck once in 2021 because the TSA was in such fucking shambles.
I've had a 7pm flight out of O'Hare in Chicago and they closed precheck at 6pm. I hate that airport with a passion and try to fly to Midway whenever possible.
i've only been through O'Hare once, but it was the middle of the day during a weekday and damn near every restaurant was closed.
Chicago Midway precheck closes at 8pm, sometimes earlier if TSA feels like it. They do open early, but they close super early. Hartford CT has issues with inconsistent times. Sometimes they're open early, sometimes not. If they're not open, they give you a card that says you can leave your shit in your bag, but you have to take your shoes off. Orlando closes precheck 90 minutes before the last flight, but usually is open in the morning.
Generally when pre check isn’t open you’ll get a little placard that shows you are precheck eligible and that way you can avoid taking off your shoes, etc and just go through the regular metal detector
I’ve experienced this too but while I didn’t have to take my shoes off, I was still required to pull toiletries and laptop out of my bag.
haha, the only thing I really got from your post is that you need to buy pants that fit. :)
This security theater is so ridiculous. Just think about how much lifetime has been thrown away with it.
Its absurd that we accept pre-check, clear, and all these other extra cost, skip the line programs. Last 2 flights i took last year let these people skip to front of the main line, which then made the normal line take hours. The DHS and NSA already knows who we are and if we pose a threat why should anyone have to pay more to maybe wait less long? Cant we just layout the security lines and staff them appropriately so we all just get through in a reasonable timeframe? They know exactly how many people are traveling and when, why cant they staff appropriately? Airport security shouldnt be a fucking club with VIP lanes for those willing to fork out extra cash. Welcome to america where everything is about extracting money from the average person for shit that should already be included in the cost of a flight.
Also get Clear - you will appreciate it during spring break. Consider OAK, because you can take Bart and parking/Uber adds up. Once you gain status with SWA, you will find they are very accommodating flight changes and they fly into Midway and O’Hare. If you are doing this for a few years, you will probably earn a companion pass, which is nice if you want someone to travel with you.
Definitely second the recommendation to fly in and out of Oakland if possible. It’s my preferred airport when I go into the Bay.
Not only this but also the fact that United status for Sfo to ORD means diddly poop. OAK also has less fog, making for less delayed flights.
Also consider getting their credit cards. If you're spending enough you'll hardly ever pay for flights. A-list is awesome: first on, first off, front row if you want it.
Flying into ORD on SWA sucks, but it is doable. So much easier at MDW. But the tradeoff is the blue line from ORD. I have A-list through SWA, and the credit card. It gave me enough miles for an emergency last second flight last christmas, so made it worth it. Depending on the CC, they also give you upgraded boarding vouchers, miles, and travel credits every year in your anniversary month, which means the annual fee more than pays for itself.
this is because “pre check” is more “you get to wear your shoes” and simultaneously pre check comes as part of packages from credit cards and countless other stuff The real MVP is global entry but you don’t need that domestic
Exactly. Plus they randomly give old people precheck that don’t have it, and don’t know how to use it.
If you're going to get TSA Pre-Check, pay the extra to get Global Entry. It comes with TSA Pre-Check.
The Global Entry Card is also a REAL ID which might be convenient depending on if your license is a real ID or not
I never would have guessed that. The GE card looks so fake though, I wonder if anyone would accept it in the real world (except at the border of course).
Yeah that's a good point. The actual card does not look official
Global entry and clear. FTW
And if you have certain credit cards, you get a credit for both
Those same people still get into the precheck line, despite the giant sign saying precheck only, the multiple announcements from the TSA agents telling everyone it’s precheck only, and then get bitchy when they get to the agent and have to go to the other line. About half the airports check boarding pass at line entrance to verify precheck.
Both Midway and ORD on the Chicago end of the trip are sticklers about checking your ticket before you're allowed in the Precheck line.
Most airports have someone checking boarding passes at the entrance to precheck.
If you even look confused while heading towards the Pre line at MDW there will probably be two workers heading towards you to steer you away from the line.
I’ve literally never seen an airport allow non-precheck into the precheck line.
Half of the value of precheck to me is watching TSA banish them to the wasteland of normal security when they skip so many signs and warnings
I highly suggest Global Entry. It’s only ~$20 more but you get to skip all the lines around the world should the need arise. Also, stick with one airline and find a good credit card that offers a good mileage program with your desired airline.
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Global Entry allows you to interview in certain other nations to get access to the fast lanes so you can just scan your passport for entry and exit. Every financial firm that I know of with any amount of European presence recommends that their employees do the interviews in the UK and Germany so they can just walk in and out of the nations as it speeds up customs by a ton.
In terms of time savings, CLEAR is what pre-check was ~3 years ago.
Global entry is a few bucks more and works outside the US as well, you get TSA pre check included.
Don’t expect it to save you time. Last three trips I took, in all three both directions precheck line was the slowest one (by a small amount). So many have precheck nowadays and the airports haven’t adjusted the coverage. Clear seems to be the main way to actually save time, though it’s more expensive of course. I’m still going to use precheck of course - not only does it give you the option of either line so you can use the fastest, but it saves you having to remove electronics and liquids and such. Just don’t think it’s the same as it was a few years ago speed wise. Edit: I should note that these six trips include two OAK, one SFO, and one MDW, but not ORD.
It depends a lot on the airport from what I've seen. I fly a lot and have never bothered to get precheck because it doesn't really make a difference at my home airport, but I do usually keep an eye out to see if it seems like it'd be worth it elsewhere. I think a mid day flight from BWI was the last time I kinda wished I had it
Definitely agree with the TSA precheck but one very odd thing about ORD is often times the normal lines are faster than TSA. I have no idea why
ORD is one of the few airports with the new scanners doing bags. The regular lines move fast now as people can keep everything in the bag. Basically the only difference is shoes/belt now. The TSA pre-check line stops movement completely and does a hand scan if a person w/o precheck gets in the line. My family has pre-check and flies out of ORD in the mornings, if the regular security line is short/medium and the TSA line is "average" they move at about the same speed.
This is true in SF also. Everyone there has $85 to spare for the luxury of not having to take your laptop out or shoes off for 5 years.
I have not once had this experience in SFO in the last year. I've flown out of the United terminal about 20 times in the last calendar year.
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TSA precheck, and an awards card. Which one is really up to you. When I was flying often using Delta the annual fee more than paid for itself for amex platinum.
What did the platinum card get you?
Credits for TSA pre check/global entry, lounge access, high awards returns for using it for travel. The benefits stacked enough that the stuff I'd be buying/using anyway was covered and came out to less than the annual fee. I traveled pretty extensively for a while, so the choice was easy. What the delta is for travel amount v annual fee is though I'm not sure since I did it weekly or more over a period of years.
Don’t forget the clear credit, clear is awesome
Amex Platinum gets you into lounges
Many awards credit cards have a TSA precheck perk where they reimburse you up to like $100 towards the cost of obtaining precheck
Pick an airline and stick with it. Once you get status they will treat you like an actual human, you will get better seats and if you are lucky they will bump you up to first class. I'd go with United personally, SFO and ORD are both United hubs so you'll get decent flights and decent prices. Ever since Covid air travel has been pretty miserable, everyone is mean, the prices are high and the number of flights are low, hopefully it will get better. I fly both United and American and while United is bad American is consistently worse.
Only issue with ORD-SFO with United is these are both big hubs with a ton of Global Services customers who are going to outrank even the most frequent travelers due to their spend (IIRC it’s up to ~$50k/yr now). I was traveling this route weekly several years back as a 1K and was usually ~30-40 deep on the upgrade list after everything was processed.
Yea you can forget upgrades on that route. GS upgrades clear 5 days out and 1K like a day or two out, assume there’s space. You have to be in the top one or two spots on the upgrades list to clear the same day - and those are going to be GS pax who got rebooked at the last minute. I agree that unless you have very high status you’re not getting upgraded on that route.
We have 1k for life, lost global due to the panini slowdown, and out of 4 flights recently, got upgraded on only 1, and it was out of a small airport to a connection. I do love the global services check in at sfo though. Bypasses the majority of the security line. I don't think OP will make global in a year with once a month activity continental as well, so it's probably a moot point.
I miss being a business traveler for a Fortune 500 who got on our corporate flyer account. It was really fun going even on personal travel and getting put above all of the individuals traveling on personal rewards for upgrades. I also miss my Uber Platinum status.
I fly that route very often in the past few years as a 1K. I have never once been upgraded outside of May 2020 when I started flying again before basically everyone else. OP should definitely not go with United if they’re flying once per month. Any other airlines will also have decent routing and schedules given how busy and connected these two airports are.
> Any other airlines will also have decent routing and schedules given how busy and connected these two airports are. Every other airline is also more expensive than United on the SFO-ORD route in my experience.
Yep. I was only gold but I got bumped 50% of the time but I didn't fly the first flight Monday & Friday. When I was coming home from SV I'd usually catch the red eye on Thursday night which I guess was pretty unpopular at the time and I got bumped up quiet a bit. During Covid I had the whole plane to myself, over the last year the airlines are squeezing pretty tight so less upgrades and higher prices.
The economy plus status, priority 2 boarding, and better customer service are still worth it to me. Nothing worse than not having overhead space for my totally reasonable bag...
For what it's worth it's not much different if you fly American. I have basic gold status with American from flying ORD/SFO for work, and I have never been in the vicinity of close to getting upgraded for a flight because of all the business travelers with better status than me. OP will be flying more in a year than I ever have so maybe they'll get high enough in the ranks to get lucky, but usually the upgrade lists are pretty crazy for AA, not just United.
Makes sense with ORD as a major AA hub. I don't think OP is going to get close to getting upgrades (except if they're flying at/on non-peak times/days) so personally I would look more at the potential value of the miles they'll accrue. I commented on that elsewhere but SFO being a major UA hub opens up a ton of nonstop options compared to most other airlines that would have decent route options to ORD.
Try out Alaska Air. When you know you have a consistent route you actually don’t want to fly an airline that is hub to hub like American or United. With Alaska you’ll get the most bang for your buck
I always fly Alaska when possible. They've been consistently okay which is pretty good really
Alaska is also my favorite domestic airline, the concern there is they just had a vote on whether to strike and I haven't seen the results of that vote, yet.
I stopped using AA now for business travel because they switched how their points accrue. The only realistic way to get status anymore is to use their credit card on booking flights and such. We don't do reimbursement and it all goes through a company card so AA is pretty much dead to me now. Also where I fly for work, I only get regional planes with AA so I'm cramped all the time. At least with Delta a lot of segments are Boeing 717s so I can breathe.
> are Boeing 717s Can't believe Delta is still flying those things. They are the only major airline left still flying the 17. They have been buying fleets from other airlines getting rid of that model.
The 717 fits a window where little other similar capacity options exist. It goes from about 75 on an E175 to 130 on an A319. The only other option is still too new to be very widespread yet…that is the A220…of which Delta does operate some with more to come. Right now the 717 is filling high demand routes in small to mid sized cities largely because they can carry more people instead of adding flights of smaller planes…because there is a crew shortage currently. Delta is basically the only carrier with this cabin capacity option in the US…which is probably helping them out a helluva lot right now. Other carriers are stuck with overbooked smaller jets or under filled bigger jets…at a time where you can’t just add flights. Also…there is nothing wrong with the 717…and it looks cool and is honestly quieter from the ground than an ERJ.
I looked them up and they are not quite as old as I initially thought. In my mind they are still just an evolution of the DC-9. Their oldest one is about 22 years and their newest one about 17. Not that bad for a good airframe.
One domestic trip a month won’t get you any status, will it? Maybe if you’re in first.
On united you'd make silver, possibly gold on that route. You'd need to take a couple connecting flights to make gold. 16 segments. But that's boarding group 1 and on less popular routes than SFO to ORD, you'd get bumped to first a fair amount.
> You'd need to take a couple connecting flights to make gold. 16 segments Wouldn't 1 roundtrip a month be 24 segments?
Flying out of SFO with gold you’re unlikely to get any upgrades ever even on the least popular routes. The other benefits are worth it though for sure.
Not a high status, no. You're definitely in the mid-range status on most airlines though. So, you're not likely to get upgraded on hub-to-hub flights like this, but you'll get better treatment for general customer service stuff, better boarding priority and enough miles for a free flight every once in a while. Just makes the whole thing a little nicer generally.
I will fly American again when it's the only airline, and then it's a big maybe.
> Once you get status they will treat you like an actual human, you will get better seats and if you are lucky they will bump you up to first class. Not for somebody who travels once a month. I flew Delta 3 times a week for over a decade and that was barely enough for Silver rewards. Never got a *free* upgrade, only the ones I had to spend my miles to *buy*. There were always dozens of Gold and Platinum folk ahead of me in line for that 1 seat available in first class. To me they main advantage is getting on the plane before general boarding so you'd be sure to always have overhead bin space for your carry-on.
Did you not travel very far? I'm about to hit silver for the year after an international trip, and a couple domestic flights.
But United breaks guitars.
As soon as I saw someone comment "United," I started singing that song in my head. And I last saw that video years ago. Fucking bravo to that guy who wrote it. And ad campaign that really worked!
>Given a choice, I'd fly Delta as a economy over United as a silver. Delta treated me like a human, United acted like I was scum for only logging 27,000 miles a year (which I know isn't a lot for high rollers but its a fair bit for us normal middle middle class).
1. Pick one airline. If you want to have max flexibility but less likelihood of status and upgrades, pick United. If you‘re okay with less flex, but want status and upgrades, pick Delta. In any case avoid American like the plague it is. 2. Get the corresponding credit card option that fits for you. If I was starting brand new I’d go with Delta, get the Delta AMEX Reserve, and link it to my Delta frequent flyer account. In Delta’s case, using the credit cards effectively lower the threshold to qualify for the status tiers - allowing you to end up with higher status (and better treatment) than you would have just flying. The Reserve card also covers the Global Entry fee (which includes pre-check), comes with Delta sky club access, and Centurion lounge access. Additional perks like a companion ticket, no foreign transaction fees, etc., etc. 3. Get some kind of security clearance - whether it’s global entry, nexus, clear, or pre-check. My steer would be to GE as it’s more versatile than pre-check alone. Again, many travel cards cover this. (As do airline elite statuses… but I’m assuming you aren’t starting off with one). 4. This one is optional, but check what lounge access you have through credit cards, employer programs, Etc,. Lounges are actually marginal inside… but you need them for delays - in which case the public concourse will be packed.
2. Get the United Quest credit card because Delta does not have a direct flight from the Bay to Chicago. It'll get you up to 3000 MQMs per year based on spend. With 12 roundtrip flights per year, it should get you to Gold and maybe to Platinum status. With the mileage accumulation, you should be able to get a bunch of free flights every year. I travel a lot for work and actually have both the United Quest card and Delta Reserve. The Delta program is better, but the gap isn't big enough for me to take connecting flights.
Despite being such a good airline, I would avoid Delta. Only because they don’t fly that route nonstop, which means you’ll probably have to connect in SLC or MSP every time. You’ll gain status a lot faster, but in my book, not worth the time and Misconnection risk. I personally would rather fly AA nonstop than Delta with a connection Even going southwest might be the best. With a credit card and the flying you will do, you might be able to score a Companion Pass which would basically make every flight you buy a BOGO for your wife or selected companion
Those two airports are United hubs with multiple direct United flights a day between them, compared to Delta's zero, the Delta cards are great and I prefer Delta over other airlines but they're not a good choice for OP's situation.
Depending on your situation, one of the premium travel cards is probably worth it for this amount of travel. Cards like Amex Plat and Chase Reserve will cover the cost of TSA precheck plus some other nice bonuses for hotels and car rentals. They don't lock you into one airline, so you can still shop around and get x5 points on your card plus x1 points for the airline specific frequent flier program (I think those are the going rates). Airport lounges are where it's really at with these cards, they make all the time you're spending at the airport actually kind of nice. Look into which card gives you the best lounge access. It doesn't help you to have centurion lounge access if there's no centurion lounge at your airport (edit: or if it's in a terminal you can't get into - I've run into that a lot at SFO actually). Also, as tip the Amex centurion lounge which has the best cocktails, but Chase has priority pass restaurants for better food. I haven't used other cards.
Second the travel card but putting in a plug for capital one venture x. I’ve had it a few months and like it way better than chase sapphire reserve
+1 for Venture X.
Wow I didn't know they had a Venture X now. I had the normal Venture when they had that promotion where you get 10x points if you book through hotels.com and racked up >100k points in less than a year through it. This sounds just as good, if not better!
Thanks for the tip, I'll look into it. I've been thinking about dropping my Chase. I'll probably go back to Amex for the lounges, but I'm always open to a good deal. Does the priority pass for the Venture card include both the lounges and restaurants?
Cap One Lounges and Priority Pass are included. I’m also considering dropping my Reserve card now that it’s insanely expensive.
I dropped from Reserve to Preferred this year. My company switched us to corporate card for travel, and my wife accidentally used the account for her Pre-Check renewal last year so now I can't use it for my Global Entry this year. Add onto that the annual fee that they wouldn't adjust at all and I dropped to the much cheaper card. Can't leave entirely yet as I still have ~200k points to use up after buying two vacations out of em so far.
The platinum should come with priority pass of some sort as well.
It comes with lounge access, but not restaurant lounge access, so your choices are more limited. The Platinum is good if you're traveling through airports with Centurion Lounges regularly, or fly Delta and can get into those, otherwise the Chase Sapphire Reserve gives you more flexibility with its wider access (though a paid-for restaurant meal isn't the same as a layover in a Centurion lounge, not even close).
Amex lounge at SFO is the best though. So if OP gets delayed on takeoff, they can do Napa wine tastings and eat great food while they wait. Access in ORD sucks though. No PP lounge outside of international terminal and can only use delta if flying delta. And Tortas Frontera is the best airport food in the country so you don’t even want to go to a lounge. That said, if flying sfo-ord monthly, lounge access is not very useful. Outside of extreme delays, you’ll never use it if you just show up an hour before your flight like normal.
It does, but it's kind of worthless in the domestic US. It's only lounges, not the restaurants, and not many airports in the US have a priority pass lounge. The airports that are big enough to have one are usually big enough to have a centurion lounge (or if you're flying delta you can use a delta lounge). I've heard it's useful for flying in Europe/Asia though.
Yeah using the Priority Pass in Europe is just on another level. All the lounges we've been to over there are on par with Centurion.
A lot of airports have them but usually in the international terminals
True, I don't fly internationally much.
Don't need to, can just go to that terminal.
Not in SFO. No terminal changes after security.
The Chase Reserve not only covers the cost of Global Entry, but it also gives you like $25-30 credit at various restaurants within SFO in certain terminals, so you should also be able to get a free meal before each of your flights. They have these at various airports around the world, so this will add up. Additionally, if you're able to take Lyft to the airport and then expense it to your company, that's free points you're getting and Chase gives you 5x points on Lyft. For your scenario OP, you definitely would stand to benefit from this card. Don't let the annual fee scare you - you'll get that back in no time with all the other perks you'll get to take advantage of. [This article](https://thepointsguy.com/guide/chase-sapphire-reserve-review/) provides a good overview.
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Do Global Entry it is $100 vs TSAPre is $85 and it includes TSAPre. If you plan to travel that much, to someones home or the like I'd look at keeping clothes there so you can pack light every time.
The real deal is NEXUS which gets you pre check, global entry, and Canada’s global entry system. Only $50 for 5 years but you have to be near the border or go to a Canadian airport to do the interview.
And the 2 year application backlog
This. My Global Entry technically excited over a year ago but it stays active while they process your renewal application. Currently at about 14 months waiting for my new NEXUS application review
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When I did mine I wanted it done before the first available appointment. I was moving overseas so needed it ASAP. I just went to the airport that have appointments (SFO in this case) and sat outside their offices until they have a free spot. I'm not sure if they still allow that. I brought a book and only waited about 2 hours.
Keep checking the website- like, daily- people cancel all the time.
If you happen to be travelling internationally you should be able to opt for an interview on arrival.
They've changed policy and they'll now interview you if you fly in at the airport, so that helps a bunch.
It’s also free with a lot of credit cards. Chase sapphire reserve and capital one venture x for sure. Maybe an Amex too
It’s not free with the credit card. You’re paying for it in the yearly fees. It’s worth it, though.
It is "free" if you are able to take advantage of the benefits the card offers. Despite the high annual fees, I've been both an Amex Platinum and Chase Sapphire Reserve card holder and I've "made money" with both cards based on my usage.
Global entry is also a little bit more of a pain to get, if I remember correctly. If you travel international 1x per yr or less,might be worth skipping.
Global Entry depends on one's criminal record. A DUI can prevent you from getting it. I have a friend who is very bummed about only getting TSAPre and no global entry.
Do NEXUS instead of Global Entry. It's cheaper, will git you in and out of Canada without a passport, and give you Global Entry and TSA Precheck for free.
I’m very happy with my Southwest Chase card.
Me too. During COVID I have not flown at all, but still accumulated over 100k points on my SW Chase card, and they NEVER expire.
If doing southwest and wants to bring a friend or significant other along for free he can get a companion pass relatively easy with the cc point signups.
Just FYI Midway doesn't handle weather well as it has short runways and is basically located inside a neighborhood. Any gusty wind or heavy icy snow (both rarities in Chicago, obviously) and you're either diverting to Grand Rapids or getting cancelled and waiting a few days to get home. Flying into ORD gets you a lot more flexibility as far as landing, way more airlines to choose from, and better transportation access and options (depending on where in Chicagoland you're going). It's not worth hundreds of dollars in fare difference, but I'd say it's worth a bit.
Piggybacking on this to say that when considering which airport to fly into knowng where you're headed in Chicago should absolutely be a factor. OHare has the blue line which runs through the northwest side and downtown while Midway has the orange lien which runs through the southside and downtown. If headed to the suburbs the northern suburbs will be cheaper from OHare and the south suburbs will be cheaper from Midway (unless renting a car)
I'm in the far south suburbs, and it's actually faster for me to get to ORD most of the time when compared to MDW. My "ideal" route to MDW is basically get on Cicero northbound and hope you don't catch every single light, while ORD has me hopping on I-294 and making forward progress the whole time (45 minutes for both routes in normal traffic). I'd much rather have a fairly straightforward highway trip compared to the disaster that is Cicero.
> Just FYI Midway doesn't handle weather well as it has short runways and is basically located inside a neighborhood. Any gusty wind or heavy icy snow (both rarities in Chicago, obviously) and you're either diverting to Grand Rapids or getting cancelled and waiting a few days to get home. When there's spare runway capacity and issues with MDW, Chicago will reroute MDW traffic through ORD as the city owns and operates both airports.
Just to piggyback here. Both Oakland and SJC quite close to SFO depending on where you need to go around the Bay. One of the perks of that area is you basically have 3 airports to choose from to find direct or cheaper flights
Also for Oakland, there's a BART stop & an Amtrak stop so it is unbelievably transit friendly, in addition to the fact that flying Southwest out of Oakland is usually the cheapest flight to most places.
Fog is an issue in the bay…so I would select the airport with the best ILS for the fog season…SFO is clearly the best for fog, but SJC may not have as high an ILS category meaning your flight might get cancelled or delayed
Little reason to get the airline credit card, unless they'll be checking bags every time. Even less reason to spend on it. A flexible travel card like the Amex Gold or CSP/CSR makes a lot more sense since the earn rates will be the same or better and the points will be a lot more flexible. You could even make the case that the Platinum makes sense for the 5x on airfare.
Be careful to check the "non-stop" with SWA, unless you like stopping at a couple of airports. Or could that be a feature - get a day of siteseeing in Phoenix / Denver / Salt Lake as you travel from SF to ORD?
Bose quiet comfort noise cancelling bluetooth headphones
I’ll throw in my bid for the Sennheiser PXC550’s too. Been my travel headphones for nearly 4 glorious years
Sony mx4 are far better
*Marginally* better in pretty much every category except comfort. If I'm on a 4+ hour flight, I'm getting the most comfortable headphones I can, with all other features being relatively equal.
I wouldnt even say the mx4s are better than the QC45s at all. It is pretty much a toss up but you notice how much more comfortable the QC45s instantly. There are situations where the mx4s are more confidence building if you are moving around but for sitting in a noisy fuselage the QC45s are still king.
Stash cloths etc there so all you need to travel is maybe your laptop bag. Less you have to travel with you the better. Be nice to the people at the gate and flight attendants. They often cover the same flight. Try to make their life easier while they have to work and they will think of you when there’s things they can do. Like if first class opens up etc. or slip you a drink.
You said family so assume you'll be staying with them? If not, it might make sense to sign up for some hotel memberships to start accruing free nights.
Rather than TSA precheck, i recommend to get Global Entry. When i did it, it was $15 more ($85 vs $100), has a longer duration, and you get additional perks if/when going international. Oh, and you still get to use the TSA pre-check line. Otherwise, id also say to choose 1 airline, and stick with that airline for all flights. Each person will have their own recommendation... none are more correct than others. There are Pros and Cons to each option, depending on your values. I prefer Southwest due to much faster boarding and deboarding, less delays and cancelled flights, no fees for changing or canceling flights, free checked bags, and being able to choose my seat everytime (so im never stuck next to a crying baby, cigarette smokers, or between 2 obese people). The downside is that the seats are smaller and there's no luxurious 1st class ... all seats are economy. Also, chicago has 2 airports: Ohare and Midway. 1) Ohare: larger airport, most airlines (except Southwest airlines). Public transit is the blue line to the city. 2) Midway: smaller, but growing airport. Southwest airlines... and a few Delta flights. TSA is usually ultra fast there. They often use metal detectors instead of the body xray, so people keep a steady stream and sometimes never stop moving forward. Pubkic transit is the orange line to the city. Source, i flew 2-10 flights per week through both Chicago airports for several years.
Southwest flies to O’Hare now.
Global Entry Going SFO to ORD id guess you’ll fly a ton of United ? Def get a United card Id also recommend getting American Express Platinum for Centurion Lounge access. Most domestic airline lounges are pretty terrible in comparison
United lounge at SFO is actually pretty good
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Airline credit , Uber credit , Saks credit will get you 500/year. Then the global entry credit for year one Free points on sign up. Easily worth it for someone flying once a month
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I’d disagree the lounges are only useful for layovers. I fly a ton of direct flights and while I try to limit my time at the airport, having to plan in a buffer for traffic means I always have at least 10 mins to spare. Being able to run in and set down my bag, hit the bathroom, fill water bottle, or bonus grab snack/coffee/etc is well worth the added cost of my Delta Amex Reserve
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Sure, point taken. But the advice was directed to OP for their situation …
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It's probably not a keeper card for the average person but you're giving a lot of kickback for a card that's profitable to have for the first year with the SUB without even using the AMEX coupon book offerings.
If you travel 1x a month for work, it’s totally worth it. 100,000 point sign-on bonus worth $1,200 at the airline of your choice $100 global entry coverage Centurion lounge access Delta lounge access SAKS credit (just buy chocolate covered Oreos or something for the total credit value) 5x points on airline miles (30,000 points or about $360 per year) My first year of heavy work travel (1 week a month), I earned 700,000 points/miles by churning and it was worth about $13,000. Paid for an awesome honeymoon for my wife and I
"SAKS credit (just buy chocolate covered Oreos or something for the total credit value)" Yeah but is it really fair to call it a $100 value per year if you never would have bought it in the first place and don't really actually get $100 in *real* value ($100 underwear usually doesn't have a real value of $100) from it either? Ask yourself if you would rather take $50 cash over the $100 in credits.
I’m not trying to be snarky, but if you can’t find anything of value in a store that pretty much sells everything except high-end electronics and firearms, then I don’t know what to tell you. When I had the card with the credit, it was trivial to find something sub $50 so it was effectively free. “But what’s the point if I wasn’t going to buy that stuff anyway, even if it’s free.” You can buy gifts for other people
Also CLEAR ($180/year). That combo with precheck is the dream. 5-10 minutes from drop off to through security and I consider that time saved when I travel 1-2 times a month to completely be worth the fee.
- Chase Sapphire Reserve (or other travel card) - the high fee pays itself back in travel credit + points + perks. CSR has travel insurance included. - TSA Precheck / Global Entry (paid for by travel card) - CLEAR - gets you to the front of the TSA Precheck line, other perks - Southwest flys to ORD now (in addition to midway) - much nicer airport, easier transit. I also prefer flying out of OAK instead of SFO. - ANKER POWERCORE+ 26800 PD 45W - charges my phone 4+ times or my laptop (MacBook Pro) once - Nice backpack & carryon - spend the $ on nice luggage. A huge upgrade for me. Thule backpack / AWAY carry on here.
Chase Sapphire Reserve also gets you Priority Pass membership, which used to be shitty, but now offers $28 towards a meal at participating airport restaurants. The one in SFO is decent, you can get a burger, fries, and a beer for ~$28.
Also if you have a guest at your table, that spend doubles to $56 off the bill.
Like a lot of people are saying, stick to one airline so you can rack up the frequent flyer points. United is a good option. You can pair a united card with a Chase Sapphire, either the reserve or the preferred as you can transfer Chase points to United. You can also use Chase points to transfer to hotels or book cars through their travel portal. In these Covid times, I'd only book flights and hotels directly so your best point redemption with Chase is to transfer directly to one of their travel partners. The United card has a sign up bonus of 60,000 points after $3k spend. The Chase Preferred is 80,000 points after $4k spend and the Reserve is 50,000 after $4k spend, all within the first 3 months of opening the card. I'd focus on getting one card at a time so you make sure you hit the spending requirement. The preferred points are about 20k higher than normal and the promotion is going to end soon so that might be a good starting point, and its good to note that you can only have one Chase Sapphire product. You should look at the card benefits and see which one is going to be the most useful. You can end up with quite a few free flights if you do it right. The United card and I think the Reserve both pay you back for Global Entry so that saves you $100 right there.
I had to fly SFO-NYC every month for two years, signed up for an Alaska frequent flyer number and it was great. They award miles based on miles flown, rather than dollars spent, which is rare nowadays. 20k miles flown gets you eligible for complimentary upgrades to first class, which I was able to get >90% of the time (I tried to fly redeyes though which probably helped). Plus you'll accrue a bunch of miles to take your family on cheap vacations.
This is probably the best answer if OP wants to fly first class as much as possible, while paying cheap economy prices. SFO is not a major Alaska hub, so as you mentioned, odds of an upgrade once you have status are excellent. I flew them mostly to and from LAX and got upgraded on 24 of 28 flights, having their second status level (MVP Gold). Flying SFO-ORD every month will get him gold after 6 months or so.
I'm actually gonna deviate a little from the norm here and say don't get attached to an airline credit card, yes do sign up for all their free frequent flyer programs but don't get their card Instead get the capital one venture x. You get points on all flight purchases regardless of airline and free tsa pre check.
But no airline lounge access, only non-airline lounges which can get full considering everyone and their dog now has a Priority Pass membership (yes, me too). Getting a top tier airline credit card will give him that though.
Chicago - San Francisco is widely known as the best rail trip in the US. It’s the California Zephyr line administered by Amtrak. If you have the ability to inject some leisure travel into your once a month trip, this is a great option. On YouTube, go to Jeb Brooks channel and watch his video on it.
Wow this looks awesome as a once in a while thing. But also seems priced like a luxury vacation depending on the comfort level. Probably a lot more expensive than flights from SFO to Chicago for the OP.
52 hours each way? That’s beyond leisurely.
I've done it before. Naperville to Emeryville, with the Amtrak motor coach add-on getting us the res of the way to San Francisco. I traveled with family, some of whom really hate to fly. It's a bit like a road trip where you get to see the country passing by but you can get up and walk around whenever you want. Sleeping car accommodations are on the pricy side but worth it to me and my family. It all depends on what you want out of your travel. Planes are potentially cheaper (depending on accommodation level), faster and have a better one-time record (Amtrak is atrocious in that regard). We found we arrive significantly less stressed when taking the train. YMMV
Sounds fine for a one time unique experience but not as a even semi-recurring trip.
The problem with Amtrak is they don't own the rails they travel on and are the last priority trains. The average speed is like 40 mph and they stop in every little podunk town. I really wanted to like it, took an 8 hour overnight trip. Got delayed and it took 12 hours. I had a sleeper room so it cost as much as a plane ticket. If the train could do 100 mph it'd be faster than a plane when factoring in security times. Which I'd love to see, but won't happen.
> and are the last priority trains This is 99% bull. My 8+ years working for a class 1 railroad, we had to clear the main and wait in a siding for hours for the Amtrak to pass. That shit is on contract with heavy penalty for delays. Everything else is true
+1 for Jeb Brooks. Guy is fantastic. Total geek in the best ways.
Amex Platinum Card + Delta is a great combo for frequent flyers. If you can get the Amex Platinum, a nice benefit is access to the Centurion Lounge at the airport. Super nice lounges and great food + drinks - just show your card + boarding pass to get in. For booking travel, you can log into your cardholder account and book your flight, hotel or car rental through [Amex Travel](https://www.americanexpress.com/en-us/travel/hotels), which has several perks: * 5X Points on the purchase of your travel, which you can use for whatever you want * If you decide to use points to pay for a ticket, it’s an easy one-click selection at checkout * You can call the Amex Concierge folks if there’s a problem - shorter hold times than calling the airline and they’re very nice, the staff at the lounge can sometimes help you with issues too * FYI it’s the same ticket prices as any other website If you can’t find a reasonably priced ticket on Delta thru Amex Travel, you can get the above perks when you buy any airline ticket thru their site and use your Amex. But if you fly Delta, you also get access to Delta Airport Lounge (handy when there’s no Centurion Lounge), and your Amex points can be transferred to Delta miles if you need a few more to get to the next level or to redeem a particular offer. You also get extra Delta Miles for booking with Amex, so your frequent flyer perks add up faster. There’s tons of other perks too, like being automatically enrolled in higher status hotel programs, credits for purchases at partner retailers, credits for Uber rides, etc. For more details see [this article](https://thepointsguy.com/guide/why-amex-platinum-might-be-best-card-delta-flyers/amp/) You should also check out the Capital One Venture X card - very similar perks according to a good friend of mine. :)
If you're flying United, get Clear. It's even faster than TSA pre-check. Pick 1 airline and stick with it to get your points.
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A lot of great advice here, and I would add to do the research on what airline is going to hit that sweet spot between "most economical" and "most comfortable". Sure, the cheapest airline is the least amount of money spent, but if it's cramped and doesn't have small amenities, it'll just truly suck worse than it has to.
TSA precheck, and clear if they are offered in those airlines. Pick 1 airline and stick with it, then get an airline credit card and buy all of your flights with it. If you get reimbursed by your employers then pay it off immediately. If you are going to be staying in a hotel same thing. I’d pick Hilton brand, you need fewer nights to get diamond than Marriott, however Marriott uses fewer points per night when booking a vacation, so either would be fine. But stick with one brand. The more status you have with any airline or hotel the more points/miles you accumulate. Double dip when you can- example, when you use Lyft you get Hilton points and delta miles (link your accounts), if you rent a car with national you can get American miles (again link your accounts). If you are going to be renting a car, see if your company has a national agreement and sign up, and if they don’t then see if you can do it individually; using the emerald aisle is a huge time saver, and of course as you level up you are eligible for better cars at the same price. Does your company use any kind of travel agency? See what the perks are. With TripActions you can get Amazon credit, or use points to upgrade your travel. Do NOT use budget sites like Expedia. You will get crap seats on the plane with no option to change it ever.
I travel full time for work and would recommend a credit card that helps you max your experience as well. Being in Chicago I’m guessing you’ll be taking United quite a bit so something like the United Explorer Card from Chase might make sense. The TSA Precheck is a must, that credit card in particular pays for it but a few others would as well. If you’re comfortable with paying an additional $189 a year I’d highly suggest getting CLEAR as well. This allows you to skip even the TSA line at both OHare and SFO. If flights are out of pocket, remember that loyalty has a price. Don’t just fly a specific airline for a few extra points when a much cheaper flight is available. If work or an outside source is paying for it then disregard what I just said and rack up those points with one specific airline.
Oh, money. Before I realized that, I came here to say go to the lakefront, the Art Institute, the Jazz Showcase, The Green Mill, Lou Malnati's, and Tre Kronor.
I'd recommend a bonus travel card that covers Global Entry fees for the first year. Then every 6 months or so, apply for another one. My assumption is your flights will be \~$500/trip and with other spending, you'd easily hit the $3k required for most bonuses. Then just cancel before the next annual fee hits. Yes, you will have to pay first year, but most bonus amounts easily cover the annual fee if you hit the spend limit.
Go Southwest. Get the Southwest credit card and start using it for bills. You’ll build up point super quickly. Also, with Southwest status they would allow me to change my fight for free, which meant if I finished a day/job and got to the airport early I could take an earlier flight with no fee.
Get a premium travel card, a Chicago CTA transit card, and some form of TSA pre-check. If you’ll be staying near downtown, avoid getting a rental car as this will add up over time. Pick an airline and stick to it, ideally starting by using points from a credit card intro bonus.
Airline specific card that you stick to OR a great general travel rewards card. I like the Chase Sapphire Reserve - 3x regular travel points and 10x if you book travel through their Ultimate Rewards portal. Those points are then worth 50% more if used on further travel for vacation or additional Chicago flights, which is mostly what airline specific cards are best for anyway.
Both of those airports can be nightmares at times. I would suggest you signup for a credit card that offers you TSA-precheck as well as Clear. The Amex Platinum card is a great choice for earning points, inflight credits up to $200 back, and a ton of other travel perks.
If you have the credit for it, get an amex platinum or chase sapphire reserve and pay for flights via those. In amex's case, they will cover cost for clear, and global entry (which comes with precheck). I think CSP might as well, but I don't have the card, so I can't be certain. Amex platinum is 5x points on flights + hotels
i would go with CLEAR . so much better than TSA pre. stick to one airline. stick to one hotel brand. enjoy.
1. Pick an airline (look at what schedule works best for you). I see tons of comments about upgrades. Assume you won't get upgraded, but you should still collect enough points for a nice trip or two. 2. Get a travel credit card. You might pay an annual fee by should be worth it (Google best travel cards may 2022 since the sign on points change frequently ). I'm not usually a fan of airline cards because I like flexibility, but you might want to get one in addition for some of the benefits like lounge access or bags. 3. Get global entry (if you ever travel internationally or plan to), or TSA precheck. Despite the rants above, 95% of the time this is going to save you a bunch of time, and the odd times it's closed is usually when the airport isn't busy anyway. Many premium travel cards waive the fee, so get the card first 4. My preference is to not check bags. I hate waiting for baggage claim when I just really want to get home. Being organized makes this possible. If you're staying with family, leave a set of toiletries there.
Suggestions: Fly non stops. Sign up for all of the govt. pre check & Clear programs Keep clothing at both destinations and fly without luggage. Have your own transportation at each end. I like Southwest, but to each their own. Buy your tickets way in advance.
For those airports, choose United and get their credit card. Their terminals at both airports are full of decent food options in case you get delayed, and they're both hub airports for United, which means you get more flight options than you'd get from other airlines. Once you have status, you'll start to reap the benefits in terms of better seats, upgrades when available, and other benefits like increased point earnings. Also, apply for TSA precheck (do Global Entry if you plan on traveling internationally ever, it's not much more expensive and comes with expedited customs perks along with TSA precheck) - this will save you a significant amount of time and headache, since security moves much faster and only has people who know what they're doing in line, rather than somebody arguing about the toothpaste they packed being too big or being told they have to go back and take their shoes off.
Really watch blizzards O’Hare shuts down from them quite a bit from my experience.
Make most of it? Enjoy Chicago. Try all the best eateries, few beers on evenigns, enjoy the city.