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Positioning one's rectum directly onto the air intake of the victim's sleep apnea machine then farting, thereby pressurizing the evil stench before slamming it at a high rate of speed and pressure through the mask , nose and lungs of the unlucky victim.
After stealthily entering the abode of mine enemy with the intent and malice aforethought of delivering unto him a Chicago Sunroof, I looked upon him did see that he wore a sleep apnea mask. And this was bad, for a mask would surely be of hindrance to said delivery. And so I thought hastily and did contrive of a new delivery system. A system even more heinous than usual. And hence I did drop trou and placed my rectum directly upon the air intake of his sleep apnea machine and did unleash the darkness that dwells within my bowels, hence, inventing the Chicago Sunroof Turbo.
by Seven62 February 21, 2015
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Chicago Sunroof

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An act performed by a young Jimmy McGill (aka Saul Goodman) on the TV show "Better Call Saul" which landed him behind bars. The specifics of this act are unknown, but it led to him being charged with assault, destruction of property, and a possible sex offense. Though Jimmy appears to think that a Chicago Sunroof is a harmless prank, the authorities believe otherwise.
Jimmy: It was a simple Chicago Sunroof!
by Time4Pizza February 16, 2015
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chicago steamer

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The same thing as a Cleveland Steamer, but with a fart added, in honor of the windy city.
<inkedmn> man, strike wouldn't let me do him til I promised to give him a chicago steamer.
by kmj January 20, 2003
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Chicago Stare

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A reference to music audiences in Chicago, Illinois who are primarily comprised of 18-25 year-old hipsters whose glassy-eyed apathy seemingly contradicts their voluntary financial investment for ticket prices (usually paid for by their parents). Reports of "Electrifying" and "Dull" performances alike from these audience members are uttered from identical, expressionless faces.
In no other U.S. city do so many under-appreciated, self-published music critics gather for the communal enjoyment of music as they do in The Windy City, where they may collectively tranquilize entertainers with The Chicago Stare.
by Phil-z January 16, 2011
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Chicago Style Hot dog

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The ultimate in foodstuffs, aka Chicago Dog

consists of:
mustard
onion
sweet pickle relish (usually neon green)
a dill pickle spear
tomato slices or wedges
sport peppers
a dash of celery salt
steamed sesame seed bun
Vienna Beef Hot Dog

NEVER EVER put ketchup on a Chicago Dog, or there will be consequences
Tourist from Kansas: I'll take a Chicago style hot dog, with ketchup
Big Willy: Whatchu say?
Tourist from Kansas: I wanted ketchup on my wiener
Big Willy: *shoots him*
by FatJoker February 24, 2008
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The act of male masturbation where your hand is reversed. (Thumb and index finger towards the shaft towards the balls) and stroking slowly in a fluid motion.
kyle did you jerk off today?

Yea but I had to switch it up so I went reverse-grip Chicago style
by Buster Miller August 2, 2015
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chicago-style

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to perform an action without wearing pants.
"i posted this defenition chicago-style."
by Chainsaw Dudley March 31, 2003
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