great chicago fire

Is when you eat too many Chicago style hotdogs (with every thing one it) and when you take a crap your ass is on fire

HOLY CRAP! i shouldn't of eaten those hotdogs my ass is burning harder then great chicago fire

by that one guyy July 26, 2011

Chicago Drive

When you take a dog into the mountains or a neighboring town and let them out and drive away

When i was a kid my dad took my dog on the Chicago Drive.

by Miklyn February 7, 2024

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

Chicago Special

A classic dish from globally renown food capital of the world, Chicago, consisting of 5 lbs of french fries covered in several overly generous dollops of cum followed by a shot of Malort. Ask any Chicagoan what condiment they eat their fries with and they'll tell you CUM. Often considered one of "the classic foods synonymous with Chicago" and "the next best thing since deep dish pizza". Originally popularized on the south side Maxwell Street district.

Me and the boys headed down to Hawkeye's for a Chicago Special.

by Chicago Native Born Boy July 26, 2021

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

growing up in chicago

The best part of growing up in Chicago.

Interviewer: Best part of growing up in Chicago?
Johnny (uhhhh face): uhhhhh... Growing up in Chicago 😬

by Amphibian Requesting death November 30, 2020