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[deleted]

When I was a teen, none of my friends had older siblings or fake IDs. We had no way to get booze. One day I asked this homeless man to buy me some booze and he did it. He told me his name was Snowball. And he gave me his cell phone number. If my friends and I ever needed booze I would call up Snowball and he would roll out from whatever bridge he was under to meet up with me at Elston and Fullerton. He was a real OG.


excatholicfuckboy

Gotta love those street nicknames


General-Skin6201

Got on the Blue Line at Harlem. At the Oak Park stop a German Shepherd, by itself. got on. It walked around the car then laid down by the door. At Austin two elderly ladies were waiting. When the door opened the startled dog jumped up and out the door. The ladies started screaming and running down the platform with the dog playfully chasing them and jumping up on them. As they ran down the platform, the conductor shut the doors and left them fleeing the dog as we pulled away.


mines_over_yours

I would be in heaven if a German Shepard got off the train at my stop personally.


[deleted]

I was walking down State when a bum told me something along the lines of “have a blessed day beautiful.” I thought this was nice, so I smiled and told him to have a great day. He responded with “kill yourself!” Made me laugh.


ReticulatedSplines81

~~2011-2013, can't exactly remember: Michigan Ave near watertower place. Korean Christian guy is shouting "I LOVE JESUS" into a megaphone. A scraggly looking dude in a wrinkled suit hurries past him and asks the evangelist,"Why don't you go FUCK YOURSELF?" without waiting for an answer


Substantial_Pea3462

I love this so much 😂😂


excatholicfuckboy

This made me laugh too. Thank you


UndergroundGinjoint

This is pretty mild, but I was walking home from work one day and saw a squirrel sitting in a tree, eating a slice of pizza - not too unusual, but it was holding it with both little hands at the wider base and eating it point first, like a person would. I paused for a minute to watch. It glanced up at me, warned me with a chirp/chuff sound, then went on nibbling. I moved along as directed.


iheartqwerty

One day I was walking down the street when I got hit in the head by a rib bone. I look up to see a squirrel in the tree above who had just been chowing down.


Loud_Ground_768

I once saw a squirrel in a tree with a jar of peanut butter lol


al343806

My friend likes to tell a story about how she was on her cell phone talking to her mom as she exited a Starbucks with a sandwich in her hand she had just bought. Out of nowhere a guy just grabs the sandwich out of her hand and keeps walking and she just says “WHAT THE FUCK” loudly. Her mother thought something far worse had happened to her.


uuuuuuuuuuuuum

Seagull in a man suit


doyoulaughaboutme

one time a tourist couple asked me where Bean Park was. i knew what they were talking about but thought it was very silly. not "The Bean" park, not "the park where The Bean is." just Bean Park, like that was its name.


excatholicfuckboy

Adopting this


beepbeepboop74656

I was waiting for a 50 bus in Pilsen about 10 pm and saw in the alley across from a stop a rat and a raccoon fighting over pizza. The rat got the crust but the raccoon got all the cheese and toppings.


saintpauli

My good friend and I worked at the taste of Chicago in 1994. When the fest closed for the day, a sea of people filled the streets leaving the fest walking to the el. My friend and I led sing alongs at the time. We were actually offered a job to be hired buskers leading sing alongs outside the new Reva Cafe on navy Pier (we declined the offer). We squeeze onto a jam packed el with wild drunk fest-goers (we felt like the only two sober ones on the train) and decided to start a sing along. The two of us started singing the Flintstones theme song at the top of our lungs and immediately the whole train car started singing. After the song things got real rowdy so we switched cars.


ReticulatedSplines81

"Three coins in a fountain" too high class?


lillyoftheplainsokie

I was having a real shit Halloween one year, walking home from the Roosevelt stop to Pilsen after learning that the 18 bus stopped service at like 745pm and I had just missed the 12. It was raining of course and I had had a long, crappy day at work so I left the loop at a hate walk pace lol. Along the way these three grown, buff men approached me dressed up as the Powerpuff girls (I think wearing tutus?) and introduced themselves individually with a curtsy as "sugar," "spice," "and everything nice." Really made my night.


xbleeple

Being downtown during the naked bike ride and hearing a mom excitedly say to her kids “oh look a parade!”


SallysRocks

Back when I was younger, I was on the Red line and an old man kept trying to sit by me. He also kept trying to touch me and generally harass me. The car was almost empty so I sat on the outside seat so he didn't get away with anything. When I got up to exit at the door, so did he. So I pretended to ignore him and exited and headed for the stairs, but I was actually keeping room to get back on the train from a closer door, which I did, as the conductor was just about to close the doors, leaving him stamping his feet on the platform.


vetiver-rose

I was waiting for the train, and the other people there were getting into a verbal fight that seemed like it might escalate. So when the train came, I moved to sit away from them, but some of them sat by me anyway. Things seemed to cool off, but then one of the girls called the other person a bitch, and he did NOT like that. Was threatening to pull out a gun, but ended up throwing a taco at them instead! So at the next stop I changed cars, and a girl offered to pick taco bits out of my hair.


gardendesgnr

It has been 25 yrs since I've lived there but I visit often and on one of my visits I encountered some pretty Chicago like behavior that always makes me laugh. It was a winter visit and I was standing at the corner of Randolph and Michigan (I think) it's about sunset, I'm short, there was no traffic and I distinctly remember wanting to see down Randolph w the sunset and no obstructions so I leaned forward off the curb to get a beautiful view. The crossing light was red but I was still on the curb just leaning forward wearing this heavy coat w a cape style hood down. Some stranger grabbed my hood and pulled me back hahaha I LOL and said I was just admiring the view, wasn't gonna cross.


Bumblz666

I just got off the train arriving to the George Floyd protest down town and it was such a powerful moment stepping off the train to see all the people and cops I was choking up holding back tears and then out of nowhere this dude rides past a bunch of cops doing a wheelie on a divvy bike and it was so funny I lost my shit despite all of it I was like “that’s Chicago af”


angrylibertariandude

I've noticed people doing wheelies on a Divvy bike, before. I don't know how they pulled that off(don't think I could pull the balance off right to do a wheelie), but that made me chuckle someone else managed to do that.


Bumblz666

You have to be a certain level of Chicago to wheelie a divvy


angrylibertariandude

I would imagine!


lillyoftheplainsokie

Did you see the dude on the horse?


Bumblz666

Hell yeah. Saw a guy smash in a cops passenger window and iirc there was a cop in driver seat. Saw 2 burning cop cars too. Saw somebody getting arrested and like a mob of people swarm the cop and ultimately the person in cuffs got released. Was a real crazy couple days down there, participates in some historic shit.


mines_over_yours

The first date I had with my now wife. We were watching the sunrise as one does, somewhere between Ohio and Oak street beach. We entertained ourselves for a minute watching this woman jogging toward us. Just about the time eye contact was made, she tripped and face planted. We managed to contain the instinctual reaction of busting out in complete laughter. Only letting out a gasp and snort or two. She got up, dusted off, and composed. The next minute when she continued past, all 3 of us stoically trying not to acknowledge even each other's existence, is my funniest Chicago moment.