by Seth Rogaine July 19, 2018

She said she never performed oral sex before so I had to give her a ride on the 'ol Chicago "L" Train.
by crush relish April 12, 2021

We tried to get dirty with a Chicago bus transfer last night, but I must not have eaten enough fiber lately.
by indynerd January 5, 2012

The part of Chicago that gets the least media coverage mostly through television and film, unlike South Side Chicago, the North Side of town and of course, the Loop in downtown for some reason.
Movies on the South Side Chicago: Barbershop parts 1 & 2. Big Shots (a 1987 movie in South Side of town where a boy gets jumped by 2 punks in the beginning of the movie.) Save The Last Dance (2001) where a young ballerina moves in with her dad on, yes, you guessed it, on the South Side. I never see movies that happen on the west side of Chicago. Yes, the west side Chicago is of urban decay, but so is the south side.
by JamilBro August 22, 2007

"Did you see that fat chick Mike took home last night?"
"Yeah, he was going to make her eat a Chicago Pound Cake."
"Yeah, he was going to make her eat a Chicago Pound Cake."
by Stevovich October 19, 2009

Big brother surveillance in Chicago. http://www.thetruthaboutcars.com/chicago-street-sweeper-surveillance-to-boost-revenue-beyond-17260300/
by chitown23 October 7, 2008

Titty fucking a girl, but instead of kneeling over her stomach as you do it, kneel over her face. As you thrust back and forth between her breasts, your ass crack rubs up and down over her nose, as if she was in a wind tunnel.
Thank goodness I had washed my ass crack before my date ... that girl wanted me to give her the Chicago Wind Tunnel!
by Tuffy May 26, 2005
