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
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My parents went out for the night so i stole a condom from my dad and pulled off a Chicago Sunroof.
by Webstar's English Nonsense February 27, 2015
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Placing your penis on the head of a unsuspecting person especially a bears fan in a public place
I totally gave Mike Ditka a Chicago sunroof
by dirty beaner February 17, 2015
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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 22, 2015
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