the act of a male ejaculating through a Red Vine, followed by the female sucking all of the semen out. Consumption of the candy afterwards is optional.
by bigdog4448 June 13, 2020

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!
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

by Not Young Honey February 21, 2021

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

by B&E9 December 8, 2020

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?”
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

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
