Chicago Carwash

When one dedicates in another’s opened car sunroof.

Johnny left his sunroof open and Mike gave him a Chicago Carwash

by Butternts63 June 6, 2018

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 baptism

Walking in the door and getting hit in the head with a fairly large dildo.

I loved Ebon’s story of his Chicago Baptism, as told on Late Night with Seth Meyers on June 19th 2024.

by ms2023 June 20, 2024

Chicago black hole twister

When you put cum inside one’s genitals and proceed to pull off their nipple and drink the milk when they lactate. then they proceed to get a surgery on their knee and put their milk inside until it explodes. then you get your neighbor named Timmy and proceed to open his rectum and get the booty crumbs, then proceed to fuck to fuck someone until a black hole appears and sucks up everybody including the earth.

David: bro I just gave Bonnie blue the Chicago black hole twister, dude it was crazy

Bonnie blue: *autistic noises*

by The Chicago menace July 2, 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

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 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