the Chicago 7

slang;Couldn't get the job done!

the Chicago 7 really Chicago 7'd

by close....but no cigar June 26, 2004

Chicago Workboot

While she's asleep, shit in her shoes. Hide in the closet in the morning, and masturbate almost to the point of ejactulating. When she puts on her shoes, she'll slip and fall and when she is on the ground, spooge on her face.

I totally gave that skank a Chicago Workboot this morning

by Jordan L. Gibson October 9, 2008

Hot Chicago

When someone takes a shit on your face while it is covered only by a piece of clear plastic wrap.

Oh, no not another Hot Chicago!!

by poo on you May 10, 2004

Chicago Deepdish

When your fucking a girl in the ass and about to cum, pull out while you are spreading her buttcheeks to gape her asshole and gizz in and around the rim of her asshole so that the gizz forms a "pizza crust" like formation around her asshole.

I gave that skank the dirtiest chicago deepdish

by Loxdap December 18, 2008

Chicago politics

A political environment or arena where any scrawny, half black kid from Hawaii can actually profit quite well from shady business deals in the most corrupt city in America...in a system that makes plenty of money for its downtown political and business leaders and their bankrolled "friends" and for the clean white folks who live in the burbs, but leaves its dirt poor and homeless far behind.

Hey everybody, let's let Chicago politics into the White House...and we'll call it "hope"

by Buddy Knox March 24, 2008

Chicago Sunroof

The act of dedicating through the sunroof of a vehicle.

"Slipping Jimmy gave that prick a proper Chicago Sunroof for sleeping with his wife."

by bokonon82 April 6, 2015

a chicago bear

A girl who has a nice body, but ugly face. I.E Nice helmet, ugly uniform.

Fergie is such a chicago bear.

by bjames August 3, 2007