city of chicago, most stupid ass tourists call it tha windy city, and u gonna get a bitch ass look from sumbody dat is a native frum tha city, like me!
toruist: "chicago really is tha windy city!"
me:" shut yo stupid ass up dis be CHI-TOWN BABY!"
by showstoppa August 14, 2006
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When a male is about about to bust in a girl's face, he pinches off his load and makes grunting noises like he's ready to cum in her face. She blinks her eyes like she's in a windgust, and then he blows it in her hair.
Dude, last night, Wes, from Chicago, gave this girl a windy city! She was so pissed!!
by zimmm421 June 14, 2009
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Having a chick fart in your mouth and immediately open-mouth kissing the fart into her mouth.
That Karen chick said she was down for a windy city, but she just couldn't fart.
by H.J. Washington August 5, 2007
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The act of licking the anus and it's surrounding areas while the receiver lets loose a mixture of gases that are byproducts of the digestion process known as flatulence.
Your mom asked if she could toss my salad. I told her I had 3 supreme tacos and double beef burrito for lunch. Therefor it will be of the Windy City Salad variety.
by RoundhouseKick September 25, 2009
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A person who constantly swerves from left to right while slowly walking on the sidewalk. This behavior often results from a preoccupation with a cell phone, gaping at skyscrapers, or a general lack of awareness.

Windy City Drifters are commonly encountered in crowded areas of Chicago and block the path of walking pedestrians. They have the greatest impact on foot traffic during rush hour but are an annoyance at all times of the day.
It took forever to walk from the train to the office today. There were windy city drifters everywhere. I felt like punchin' someone in the back of the head.
by Kenny Canstacker January 8, 2011
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The act of blowing air into another person’s asshole
Hey baby, flip over and let me give you a Windy City Whistle
by Pharr February 23, 2019
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