Chicago penetration

The act of sticking your glock up your loved ones ass ...letting her shit on it then sticking the glock down her throat
I have my girl a Chicago penetration last night
by Randomshit34 February 09, 2017
mugGet the Chicago penetrationmug.

Chicago Car Wash

The date night was going great until the 5 star restaurant turned into a Chicago Car Wash.
by cockwork October 05, 2019
mugGet the Chicago Car Washmug.

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 01, 2021
mugGet the Chicago White Sockmug.

Chicago Mayor

Hym "Chicago Mayor says his kids are more important than everyone else! You hear that folks? Parental Dictatorship! We live for them and their fuck trophies! Can't pay your bills? Doesn't matter. 'My kids have soccer practice!' Robbed out of a billion dollars? 'Shouldn't have given more of a shit about my mongrel kids!' We live to be harvested by fat-cock Parental Dictatorship!"
by Hym Iam February 07, 2024
mugGet the Chicago Mayormug.

Chicagoed out

Chicagoed out is a term meaning of being drunk, or really really high, even cross faded. Because Chicago is disoriented and ignorant city. It’s an unsafe feeling when chicagoed out feeling like you are Chicago.
Group of friends: Let’s grab beer.
Person: A partner B is already chicagoed out.
by Jo icamp April 11, 2024
mugGet the Chicagoed outmug.

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
mugGet the Chicago french toastmug.