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

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

Chicago goatse

To make monkey noises while spreading your buttcheeks all while forcing all blood pressure to your rectum.

“Hey man, did you see TheDooo when we drove by? I think he was doing the “Chicago Goatse” on the sidewalk…”

by JvstSayin178 January 16, 2025

Chicago bears

A more entertaining football club than the New Orleans Saints (even if they lost the game).

The goody two shoes Saints were crying about cheap shots after getting hit twice by the Chicago Bears. A saint just doesn't have the same effect on an opponent as a bear, a player pulling out a crucifix and telling an opponent they will burn in hell for what they did doesnt have the same effect on somebody as hitting them twice, even if they were sucker punches in the helmet.

by Solid Mantis November 3, 2020

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

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

Chicago Oyster

What comes out of your nose after doing large amounts of cocaine for an extended period of time.

Man, Smitty served up Chicago oysters all over that hotel room in Atlantic City.

by jaybronee October 10, 2020