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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
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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
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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
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Chicago Stir-Fry

Boiling completely liquid diarrhea in a croc pot and using it as a popular Chicago substitute for gravy. Often seasoned with smegma or red pepper flakes flakes
Billy: yo Tony can I get a little chicago stir-fry on my dog?

Tony: Tell when to stop pouring billy!
by OfficiallyDrDubious May 10, 2025
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Chicagoed out

Chicagoed out is a term meaning of being drunk, or really really high, even cross faded. Because Chicago is disoriented and ignorant city. It’s an unsafe feeling when chicagoed out feeling like you are Chicago.
Group of friends: Let’s grab beer.
Person: A partner B is already chicagoed out.
by Jo icamp April 11, 2024
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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
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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
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