Chicago Freestyle Bandit

When a male urinates inside his partner.

Bro, I had like six liters of beer before we got to it. I had to go so bad, I accidentally became the Chicago Freestyle Bandit. I wonder if she'll want to see me again.

by Curtis Claymore April 15, 2025

Chicago Surprise

The act of leaving ass pennies around town for unsuspecting pedestrians to find.

I was walking by the Willis tower when I bent down to pick up something shiny. "Wow," I thought, "a lucky penny. My luck is surely changing!" I couldn't have been more wrong. As I drew the penny near my face for a closer look, I could tell that I was being punked. The smell of copper laced with rotting feces left no doubt. I'd just found a Chicago Surprise.

by DOTCOM May 9, 2017

Southside of Chicago

Dangerous side of Chicago, full of shootings and dangerous wars. - Stay away at all means.

Ay foe, dem niggas onna southside of chicago crazy asl.

by .3mxi December 28, 2024

Chicago promise

Certain people like giving out promises without the intent of carrying them out. For some reason, a significant amount of such people populates Chicago. This kind of people is called bullshitters, and the kind of bullshit promises they give out is called a Chicago promise.

-- This dude said he'll bring over some molly this Friday.

-- You sure it wasn't a Chicago promise?

by othra May 13, 2024

Chicago Drug Mule

Cocktail made with Jeppsen’s Malort

1.5 oz Tequila
0.75 oz lime juice
0.75 oz cranberry juice
0.5 oz Jeppson’s Malort
2 oz ginger beer

‘Malort is undrinkable’

‘If you mix it into a Chicago Drug Mule, it’s only mildly unpleasant’

by waterbaby8391 November 24, 2022

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

Chicago Style Driving

Chicago style driving is the action of driving the opposite direction of a NASCAR track, often used a formal excuse for trolling or when someone forgot the proper direction. The style invented by the roblox player UptightEpicman22, published by Secured_Noodles and pingo_boi

Driver 1: “You’re driving the wrong way stop it”
Driver 2: “I’m Chicago style driving”

by Secured_Noodles September 22, 2025