A driving maneuver in which a vehicle changes multiple lanes without pausing in each lane, in a "sweeping" motion. Named as such for the asshole semi truck drivers who utilize this method on the highways into and out of Chicago.
Driver: "The fuck?! That guy just cut me off from across the highway!"
Passenger: "Excellent Chicago Sweep, 10/10."
Performed by a pair of males, first a dead prostitute must be located, then a coin flipped. He who wins the coin toss must jump on the dead prostitute's stomach, while he who loses the coin toss places his mouth over the dead prostitute's vagina and eats whatever contents are projected forth.
Dude this ho is dead, flip a coin and we'll give her the good ol' Chicago Street Sweep.
when you get a boob job from a chick when she's laying down and just as you're about to ejaculate, hold your penis in one hand and go toaster streudal style on her bare stomach.