A shitty industrial city next to Lake Michigan that is home to the Bears, the Cubs, and one dude who is PISSED THE FUCK OFF that he can't get any action named JOSH BOYLE.
Chicago: a city where dreams go to die.
by Tuccimustdie March 1, 2020
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Chicago. One of the most amazing people. He will always try to comfort you while being a complete idiot. He’s usually out of a relationship and not willing to get back in. Has trust issues but it’s fine.
Yo did you hear about chicago

Yea dude my mans just jumped of a cliff
by Iamirresponsibleinways December 5, 2019
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The act of sticking your glock up your loved ones ass ...letting her shit on it then sticking the glock down her throat
I have my girl a Chicago penetration last night
by Randomshit34 February 10, 2017
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a bed of iceberg lettuce with either a pork chop or cut up hot dogs on top
I'll order a Chicago salad as I'm trying to healthier.
by Oceanic16 November 8, 2021
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hes bo and hes from chicago, has some d1 prospects but dropped them for a monk. hes bo from chicago tbh.
by bdustdadawg March 6, 2023
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Four Steps: Go to a strange place with no sleeping arrangements, find a girl, bang her, then stay at her place.
I couldn't afford a hotel so I had to pull my Chicago parachute.
by jugghandler March 28, 2016
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A more entertaining football club than the New Orleans Saints (even if they lost the game).
The 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
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