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Chicago Freestyle Bandit

When a male urinates inside his partner.
Bro, I had like six liters of beer before we got to it. I had to go so bad, I accidentally became the Chicago Freestyle Bandit. I wonder if she'll want to see me again.
by Curtis Claymore April 15, 2025
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Chicago Surprise

The act of leaving ass pennies around town for unsuspecting pedestrians to find.
I was walking by the Willis tower when I bent down to pick up something shiny. "Wow," I thought, "a lucky penny. My luck is surely changing!" I couldn't have been more wrong. As I drew the penny near my face for a closer look, I could tell that I was being punked. The smell of copper laced with rotting feces left no doubt. I'd just found a Chicago Surprise.
by DOTCOM May 9, 2017
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West chicago

Safe not dangerous town full of Mexicans boring really boring nothing to do also known as west cheesy n idk what else yall good luck if you come🙏🏽🙏🏽
“U ready to go to west cheesy
“Yh Lol”
“Bsmla”
“Why west Chicago
“Bc like it small”
by Alicruz May 26, 2024
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Chicago Special

A classic dish from globally renown food capital of the world, Chicago, consisting of 5 lbs of french fries covered in several overly generous dollops of cum followed by a shot of Malort. Ask any Chicagoan what condiment they eat their fries with and they'll tell you CUM. Often considered one of "the classic foods synonymous with Chicago" and "the next best thing since deep dish pizza". Originally popularized on the south side Maxwell Street district.
Me and the boys headed down to Hawkeye's for a Chicago Special.
by Chicago Native Born Boy July 26, 2021
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Chicago Hair

A term used to describe a young man who is balding or trying to hide his bald spot—often by wearing a hat. The name “Chicago Hair” comes from the windy reputation of Chicago, where a strong gust could easily blow off a hat and reveal a hidden bald patch.
Man: “Let’s go swimming on the first date—so you cant catfish me with your makeup or filters.”

Woman: “Sure! And on our second date, let’s take a walk through Chicago so the wind can snatch that hat right off your head and reveal your bald spot, How’s that sound, Chicago Hair?”
by yunggravy4 April 22, 2025
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Chicago Bears Tax

A mysterious curse where any football player who signs with the Chicago Bears immediately forgets how to play football. Scientists estimate a 75% drop in skill the second the pen hits the contract. Side effects include dropped passes, missed tackles, and uncontrollable crying at Soldier Field.
Man, he was a Pro Bowler last year. Now? Looks like he paid the Chicago Bears Tax.
by 34344444 September 7, 2025
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Chicago Stir-Fry

Boiling completely liquid diarrhea in a croc pot and using it as a popular Chicago substitute for gravy. Often seasoned with smegma or red pepper flakes flakes
Billy: yo Tony can I get a little chicago stir-fry on my dog?

Tony: Tell when to stop pouring billy!
by OfficiallyDrDubious May 10, 2025
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