When 2 or more dicks are crammed into a woman's mouth, vagina, or anus.
Tyson: I heard you and Nathan had a Chicago Traffic Jam on Lori}
Wilt: yeah, they were deep in her ass
by Jedi Master Joe September 23, 2017
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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.
by The Original Agahnim July 1, 2021
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When a guy shits on a girl's chest, then titty fucks her.
Those wacky Illinois people love to give their wives the ol Chicago Chili Dog.
by James Westen April 19, 2019
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A good luck pre-game ritual for Chicago White Sox fans where your girlfriend slips on a black sock (normally used for feet) on your cock and jacks you off until you cum into the sock while you sit back, relax, and strap it down with a beer, preferably a Miller lite (or modelo if your girl is Latina)

This is similar to the Clark Street Cock Sock, which is performed exclusively among men within the gay community and into a blue sock before Cubs games instead.
My girl surprised me with the ole Chicago White Sock before the game that was so good I nutted through the sock and Giolito threw a no-hitter!
by DamnGoodCockSock April 1, 2021
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Hey Brian me and Austin are going to Chicago Diablo do you want a mexican fish taco?
by Chicago Diablo purchaser. September 21, 2010
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The Chicago Bear is when after receiving a Green Bay Packer from the bear variety of men; the recipient then finds a football field and just shits all over it. The shitting on the field may be figuratively or literally.
"Illinois football fans gather in a stadium to watch their local heroes perform The Chicago Bear. "
by Verbius VonMasturbate August 12, 2021
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