Chicago Waterboarding

When someone holds a shot of Malort in their mouth pulls their shirt over their face and has someone pour Gatorade on them.

Man did you hear Tony almost died from one too many Chicago Waterboardings

by James "charles" Whirlpool December 30, 2019

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 Chili Dog

When a guy shits on a girl's chest, then titty fucks her.

Those wacky Illinois people love to give their wives the ol Chicago Chili Dog.

by James Westen April 19, 2019

Chicago Sun Roof

When you take a big 'ol steamy shit into the sun roof of someone else's vehicle.

"Yo wtf I just got Chicago Sun Roof'd and now I gotta clean it up."

by I_DankStep January 9, 2022

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 Shrimp

When you go out to eat at a seafood place that is located in a landlocked salt water location.

As your friend is hugging the porcupine toilet, “And that’s why we don’t eat the Chicago Shrimp”

by Pkangas91 January 1, 2022