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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?”
The team people are thought to be insane if they root for after over a hundred years of no titles or championships, and people still root for them anyway, because winning is not the point of everything in life.
Not many other sports teams would keep people rooting for them after not winning for so many years, a lot of people would abandon a different team than the Chicago Cubs.
An act of beating someone down with your penis.
I just gave my mom a Chicago meatdown
A crazy cat lady who wants her cats watch her have sex
Person 1: "Dude that chick last night was crazy!"
Person 2: "how come?"
Person 1: "she had her cats in the room while we were having sex!"
Person 2: "Oh like a Chicago Cat Mom."
Absolute and utter pain caused by server lag.
"FUCK, another FUCKING CHICAGO, if I get CHICAGOED one more god damm time I'm throwing my fucking controller through my wall".
The best part of growing up in Chicago.
Interviewer: Best part of growing up in Chicago?
Johnny (uhhhh face): uhhhhh... Growing up in Chicago 😬
To make monkey noises while spreading your buttcheeks all while forcing all blood pressure to your rectum.
“Hey man, did you see TheDooo when we drove by? I think he was doing the “Chicago Goatse” on the sidewalk…”