The act of hovering directly over the face of a sleeping or otherwise unsuspecting person while spreading your as cheeks as wide as your ballon-knot permits. Next, proceed to unleash a monster fart directly on them, thus producing a stench filled wind indicative of the Windy City itself.
After a long night of felching for duckbutter, Lou Skunt decided to pay his gay lover back by giving him a Chicago Sunroof, so he cocked his hemorrhoid infested asshole over his nose and fluttered a gale force ass-bomb so windy that it permanemtly parted his mustache.
by FupaGunt February 17, 2015
A sexual position consisting of the male reclining in the drivers seat of a car with an open sunroof. The female then rides the male while her upper body sticks out of the sunroof with her boobs resting on the top of the car.
It was a simple Chicago Sunroof!
by mikezilla February 17, 2015
The act of urinating into the open sunroof of a car from the balcony of a building. Then when caught, claiming you did it because you thought someone was trying to steal the car, and you were trying to stop them. This event was reported to have taken place in Chicago's South Loop in September of 2014.
by Piltdown Man February 21, 2015
The act of hovering directly over the face of a sleeping or otherwise unsuspecting person while spreading your ass cheeks as wide as your ballon-knot permits. Next, proceed to unleash a monster fart directly on them, thus producing a stench filled wind indicative of the Windy City itself.
After a long night of felching for duckbutter, Lou Skunt decided to pay his gay lover back by giving him a Chicago Sunroof, so he cocked his hemorrhoid infested asshole over his nose and fluttered a gale force ass-bomb so windy that it permanently parted his mustache.
by FupaGunt February 17, 2015
The act of masturbating while standing on an overpass or tall building, while attempting to ejaculate onto vehicles passing below.
Rahm Emmanuel left the gay club stoned and alone. Full of self pity, he stood on his balcony slapping his giblet until he Chicago Sunroofed over a passing garbage truck.
by KissMyWookiee February 20, 2015
by Webstar's English Nonsense February 27, 2015