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

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

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

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 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 back handy

When a female relative who owns a Chicago style pizza place uses the leftover grease from a pizza to give you a hand job after closing time.

“Hey Aunt Beatrice, do you have the time to give me a Chicago back handy, I saw some leftover grease in the kitchen”

by Gripster August 29, 2023