A variaton on the cinncinatti bowtie, where the giver flatulates into the victim's face.
When giving a cincinatti bowtie to his girlfriend, he decided to spice it up and threw a windy city bowtie into the mix.
by Count Spankula April 24, 2006
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Derrick Rose, Former Bulls (soon to be) Hall of Famer was given this nickname in the 9 Years he was playing With the Chicago Bulls. Derived from the nickname of Chicago 'Windy City'

(Also given nicknames 'Pooh' and 'D-Rose)
John: Hey did you watch The Windy City Assassin, Derrick Rose drop 44 Last night against the Atlanta Hawks?

Anthony: Yes! He's definetely going to be MVP this Season.
by 3ToWon December 13, 2020
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Slang phrase to describe the popular chain of restaurants called Old Chicago.
Let's go finish the Beer Tour at Ancient Windy City!
by n81 February 14, 2012
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Cammy B was in the middle of masturbating his uncle when came the windy city rumbler, which had no effect on Cammy B on the account that he lives in Colorado, not Chicago. So he just continued stroking away gleefully.
by Bobby, Bobby Smo November 12, 2006
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the chicago windy city is where the man farts a big nasty one in his partner's mouth and said partner proceeds to blow it back in the man's face.
Dan: Yeah dude... I totally gave her the chicago windy city.
Mark: She really blew it back in your face?
Dan: Hell yeah she did.
by Face First July 14, 2006
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When semen is farted out after anal sex, with little poo pieces mixed in.
Hey man don't touch that wall, it got sprayed last night with a windy city apple turnover.
by Youdidwhat May 30, 2009
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2 gays fucking and their balls sacks are smacking.
Ed and I got together last night for some windy city mud flap.
by Poopie boobies November 29, 2016
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