Chicago Nap Time

A kindergarten sport- During nap time after the teacher has left the room, the chosen boy for the day sees how many broads he can bang before nap time is over before whatever stupid shit video is going on has ended. Rules vary by school district, but sources say this pastime began in Chicago.

Tommy- "Dammit I missed class the other day, who got to play Chicago nap time?"
Brett- "Jason did, he got a score of 5"

by Synth 2 September 8, 2019

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 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 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 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

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 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