Douglas Park (Chicago)

A shitty park in the shitty west side of Chicago, located blocks from Cook County Jail. You are likely to get shot here.

Man wounded in Douglas Park (Chicago) shooting

by Ltdani21 August 29, 2018

Cleveland Chicago Express

Shitting on someone's chest though an open sunroof.

I almost got an indecent exposure charge after giving her a Cleveland Chicago Express.

by BigDrew77 April 21, 2022

Chicago Union Station

A train station in Chicago that serves Amtrak trains from all over the US and Metra trains.

"Chicago Union Station is like Grand Central but in the Midwest."

by Milwaukeeboi148 December 18, 2018

chicago meatball sub

When a dude places his balls in a girls ass crack therefore making it a Chicago meatball sub

Jimmy made a Chicago meatball sub with my ass last night

by Horrible memes February 18, 2020

preppy chicago teens

A species on its own, the preppy chicago teens. You can find these kids at certain schools around chicago, and with an exception of the kids who were too broke to go to private school but still consider themselves “preppy” and “upper class”. Ignatius, loyola, parker, latin, regina are full of preppy individuals. These kids wear vineyard vines EVERYTHING, girls usally have a vera bradley id, lily pulitzer skirt or shorts and tory burch sandals or jack rogers. When wintertime hits chicago the preppies wear a Patagonia jacket and Patagonia snap-T fleece underneath to keep extra warmth. Boat shoes are common and girls wear hunter boots or uggs. The preppies of chicago all live in Lincoln park, gold coast, river north, lakeview and somewhat around there. On the weekends they hangout in a large group with their other preppy friends and go get tonys burrito mex (a local taco place) around lakeview. Some preppy boys don’t hangout becuase they are too busy playing hockey for a triple A team. Most preppies also have a membership to midtown, east bank club or a local country club. Usally the girls on the weekends go out to eat at summer house santa Monica, hampton social or any place with a cute wall or sign for their insta.

Hey, i wonder why there are 20 girls trying to take a photo by the “rosé” wall?
Oh thos are the preppy chicago teens ignore them

by welikechickenfried November 22, 2018

Chicago Breathing-Style

A subset of the demon slayer corp style, where the user brandishes a UZI in a Toyota Corola in his hood and drive-by the nearest project, preferably in Chicago Illinois

Person 1: Yo, Wagwan, you heard Jerry got Chicago Breathing-Style on
Person 2: Damn, the opps really pulled up huh

by Dinosaurruaronid October 31, 2023

Chicago Tour Bus

When two men stand facing each other, and place their dicks side by side. Then one of the men jerks both dicks off in one hand.

Man, last night I had a dream where I walked in on Bob doing the Chicago Tour Bus with Mike.

by Chronic Block May 8, 2018