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Chicago Hair

A term used to describe a young man who is balding or trying to hide his bald spot—often by wearing a hat. The name “Chicago Hair” comes from the windy reputation of Chicago, where a strong gust could easily blow off a hat and reveal a hidden bald patch.
Man: “Let’s go swimming on the first date—so you cant catfish me with your makeup or filters.”

Woman: “Sure! And on our second date, let’s take a walk through Chicago so the wind can snatch that hat right off your head and reveal your bald spot, How’s that sound, Chicago Hair?”
by yunggravy4 April 22, 2025
mugGet the Chicago Hairmug.

Chicago Blackhawks

Chicago Blackhawks the "best team in the league" win some Stanley Cups then come close to last in the league trade a player to the Winnipeg Jets and get him back a few years later then trade him again the the NY Islanders. The team that lost to both the Colarado Avalanche and the Arizona Coyotes just in just 2 week! Oh I can't forget loosing in the first round by the team that was ranked 16th in the playoffs and lost the round 4-1 and scored 2 goals.
Chicago Blackhawks meaning: When a team chokes twice in the playoffs in 2 years and only scores 12- Goals in 2 Playoffs
by Gardener That Loves Crib February 18, 2018
mugGet the Chicago Blackhawksmug.

Chicago Traffic Jam

When 2 or more dicks are crammed into a woman's mouth, vagina, or anus.
Tyson: I heard you and Nathan had a Chicago Traffic Jam on Lori}
Wilt: yeah, they were deep in her ass
by Jedi Master Joe September 22, 2017
mugGet the Chicago Traffic Jammug.

The BEAN (Chicago)

This monolithic and gargantuan structure of unknown origin has been the centre of speculation for centuries. The awe inspiring size, shape and sturdiness of the bean has been topic of debate since its arrival in 1738. It has become a popular attraction for mere mortals to convene.
Unknowingly co-existing with the unknown power residing inside of the Bean.

Theories of the Bean have been under speculation for many years. It is believed the government is trying to hide its true form from the public as a form of damage control. The Bean is closed off from public during the night to prevent further recordings of the supernatural happenings.

The Bean is disguised as an innocent artistic structure to the public eye however it has grown annually with rumours claiming periodical ritualistic human sacrifice correlating with its exponential growth.

Fear the unknown, fear the Bean.
The Bean (Chicago) is a structure that has been around for centuries, its true purpose is unknown
by Garads July 9, 2024
mugGet the The BEAN (Chicago)mug.

Chicago Sun Roof

When you take a big 'ol steamy shit into the sun roof of someone else's vehicle.
"Yo wtf I just got Chicago Sun Roof'd and now I gotta clean it up."
by I_DankStep January 9, 2022
mugGet the Chicago Sun Roofmug.

Chicago Cat Mom

A crazy cat lady who wants her cats watch her have sex
Person 1: "Dude that chick last night was crazy!"
Person 2: "how come?"
Person 1: "she had her cats in the room while we were having sex!"
Person 2: "Oh like a Chicago Cat Mom."
by SpankyHanky69 August 23, 2020
mugGet the Chicago Cat Mommug.

Chicago

the best fucking city around, am i right or am i right.

we’ve got some bomb ass pizza (best pizza ever don’t @me)

we’ve got some dope as rappers. love ya chance.

fucking shameless that’s a great show. and Carl Gallagher can have my children.

we know how to throw a parade too. i mean st. patty’s day that shits a hit.

home to the cubs like cmon we all know everyone’s rootin for the cubbies.

you can’t tell me you don’t think our city skyline isn’t just perfect.

so yeah chicago’s the best city.
“so you’re from illinois

“no, i’m from chicago”

damn you’ve got some bomb ass pizza”

yeah i know
by yeah i’m dope April 9, 2018
mugGet the Chicagomug.

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