chicago shoeshine

When you pay $20 to a homeless person to get you off on the side walk. Then they wax your shoes clean with a mixture of their spit and your spooge
Livingston was lost on Ohio St. so he paid a homeless guy for directions and ended up getting a Chicago shoeshine. It was more than he bargained for.
by The Sweens April 08, 2016
Get the chicago shoeshine mug.

Chicago Inferno

The Chicago Inferno is a variant of the Pittsburg platter in which the person giving the act, has explosive diarrhea over a glass table with a person underneath it, the glass may brake which commonly leaves the observer covered in blood, glass and shit
Dude,Dave got a Chicago Inferno last night!!!
by Jackie Robinson Raybam May 29, 2023
Get the Chicago Inferno mug.

Chicago Mary

Another term by JC in Chicago. This is an affectionate term for all those attractive middle aged women (MILFS) that come to Chicago on business and troll the local bars looking for a one night sexual adventure.
She said she was from Kansas here on business but, turned out to be a Chicago Mary.
by Senior Elstonia May 02, 2015
Get the Chicago Mary mug.

Chicago Strawberry

When you stick a strawberry roll into a woman pussy and eat it out of there before fucking her
Last night I gave Taylor a chicago strawberry before I gave her the cream filling.
by Tool1979 February 26, 2021
Get the Chicago Strawberry mug.

oral chicago

a sexual act also referred to as "deep dish" where a woman's sexual partner accepts her juices in his/her mouth and uses them to flavor a deep dish pizza or a hot dog
Andrew enjoyed giving Molly oral sex so much, he asked her if he could perform an oral chicago.
by Big Donkey 16 November 12, 2013
Get the oral chicago mug.

judy chicago

I hooked up with that hairy-armed pink pussy hat wearing FemiNazi after the Antifa rally and she Judy Chicago’d so loud it woke up the dog.
by Salohcin2 October 26, 2019
Get the judy chicago mug.

Chicago Sweep

Also called the Chicago Slide.

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."
by pressyglue July 07, 2018
Get the Chicago Sweep mug.