Chicago penetration

The act of sticking your glock up your loved ones ass ...letting her shit on it then sticking the glock down her throat

I have my girl a Chicago penetration last night

by Randomshit34 February 9, 2017

Chicago

A city that’s more famous than the state it’s in

Chicago > Illinois

by Keemakurry November 5, 2022

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 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 Handshake

This is a slang term referring to a handjob.

Paying to get yourself jerked off by another man

"Johnny boy went and got himself a Chicago Handshake down at Robert's. I'm surprised they have em for only 10 dollars"

by Chris Da anonymous May 20, 2024

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