Chicago Wetback

When you nut on your girlfriends back while your upstairs neighbor floods their condo soaking your entire bedroom

"I can't escape living in a place where it rains indoors. This is the third Chicago Wetback I've had in a row. I'm so over this curse"

by anonymous August 4, 2025

Chicago Facefuck

Similar to a Chicago Handshake (the drink), a Chicago Facefuck is a shot that's half Fireball Whiskey and half malört followed by an Old Style beer.

Guy 1: Hey want a shot of Fireball? (hands Guy 2 a shot)
Guy 2: Yeah sure...Ugh! What was that?!
Guy 1: Haha, you just got Facefucked!
Guy 2: Aw dammit, a Chicago Facefuck? Someone get me an Old Style to get this malort out of my mouth!

by Mizami October 8, 2018

Chicago Luggage

When some idiot doesn't clean the snow off the roof of their car either because their ignorant or were in a hurry and when they stop fast it flies backwards on your windshield blinding your field of vision instantly as they drive away laughing.

ThatJag-Off just got me with his Chicago luggage lazy bastard! Good thing I didn't wreck my car or it would of been his ass!

by Ol watchmen January 12, 2024

Chicago

it’s a city that inviting it’s a city that’s exciting it’s a city for a woman just like me!

trina vega: CHICAGO! CHICAGO!
people watching at home: ITS A CITY THAT INVITING ITS A CITY THAT EXCITING ITS A CITY FOR A WOMAN JUST LIKE ME!

by Scree December 10, 2019

Chicago Bob

THE PRIMAL ACT OF TAKING A WOMAN FROM BEHIND WHILST HER HEAD IS IN THE TOILET

Girl, I love smelling shit while getting raw dogged! He gave me a real chicago bob!

by Doris Pringle Brule June 17, 2024

Chicago Plague

The deathly illness that impacted 3 quarters of the cast of Chicago: Teen Edition.

“Jarrett is sick, he caught the Chicago Plague”

by tankert December 12, 2022

The Chicago Woodsman

The act of defecating on the back of your one night stands head before leaving their house in the middle of the night.

Mark: Did you hear what happened to Steve Last night?
Jenny: No....Is he OK??
Mark: Yeah, just got The Chicago Woodsman from his one night stand

by The Real Woodsman September 13, 2023