Chicago Paycheck

When someone gets shot.

JFK cashed in his Chicago Paycheck.

by YourSexyDad March 25, 2021

Chicago White Sock

A good luck pre-game ritual for Chicago White Sox fans where your girlfriend slips on a black sock (normally used for feet) on your cock and jacks you off until you cum into the sock while you sit back, relax, and strap it down with a beer, preferably a Miller lite (or modelo if your girl is Latina)

This is similar to the Clark Street Cock Sock, which is performed exclusively among men within the gay community and into a blue sock before Cubs games instead.

My girl surprised me with the ole Chicago White Sock before the game that was so good I nutted through the sock and Giolito threw a no-hitter!

by DamnGoodCockSock April 1, 2021

Chicago cumshot

When a guy blows his load into the barrel, chamber, or loaded magazine of a firearm then uses that firearm to blow the load onto/into the face of another person.

I got kicked out of the gun club when i gave the range safety officer a chicago cumshot.

by Jay64 July 7, 2022

Chicago Soft Serve

When you disguise shit as chocolate soft serve

I pranked Sam so hard when I gave him my Chicago Soft Serve

by JustLib July 17, 2022

Chicago

(she-cah-go) A city in the state of Illinois. To prove if somebody is truly from Chicago, ask them what block they from. If they say O-Block, whoop they ass (depending on their speech pattern). If they say Lamron, whoop they ass but not as bad because they did they research, anything else is valid.

"EEEEE Shordy she thick asl onfg! Whea she stay at? Im tryn crack onb!"
"She stay somewhea onna South Side"
"Of where?"
"New Mexico. *slaps the nigga* CHICAGO FUCKING GOOFY"

by ACEFRMDOUGLASS September 13, 2022

Chicago

City if corruption.

"Chicago is killing Illinois."

by Albino namekian October 27, 2022

Chicago french toast

Chicago French toast; first made famous by President Barack Obama at his inaugural speech— when he credited the colloquial favourite as his main staple that saw him through college.

Chicago French toast differs from classic French toast to in the distinction that it is made with bagels, and not sliced bread.

Is that a cream cheese bagel? No. That’s Chicago French toast baby.

by Walters Brew October 28, 2022