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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
mugGet the Chicagomug.

chicago body

A big body type, typical of the region, see Da Bears skit from SNL with a Chris Farley.
by B&E9 December 8, 2020
mugGet the chicago bodymug.

Chicago Nap Time

A kindergarten sport- During nap time after the teacher has left the room, the chosen boy for the day sees how many broads he can bang before nap time is over before whatever stupid shit video is going on has ended. Rules vary by school district, but sources say this pastime began in Chicago.
Tommy- "Dammit I missed class the other day, who got to play Chicago nap time?"
Brett- "Jason did, he got a score of 5"
by Synth 2 September 8, 2019
mugGet the Chicago Nap Timemug.

Chicago Handshake

This is a slang term referring to a handjob.

Paying to get yourself jerked off by another man
"Johnny boy went and got himself a Chicago Handshake down at Robert's. I'm surprised they have em for only 10 dollars"
by Chris Da anonymous May 20, 2024
mugGet the Chicago Handshakemug.

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
mugGet the Chicago Freestyle Banditmug.

Chicago bears

A more entertaining football club than the New Orleans Saints (even if they lost the game).
The goody two shoes Saints were crying about cheap shots after getting hit twice by the Chicago Bears. A saint just doesn't have the same effect on an opponent as a bear, a player pulling out a crucifix and telling an opponent they will burn in hell for what they did doesnt have the same effect on somebody as hitting them twice, even if they were sucker punches in the helmet.
by Solid Mantis November 3, 2020
mugGet the Chicago bearsmug.

Chicago goatse

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…”
by JvstSayin178 January 16, 2025
mugGet the Chicago goatsemug.

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