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Little Chicago 

Little Chicago refers to a city called Hamilton just North of Cincinnati in Ohio. It got its nickname in the 30’s due to Gangsters from Chicago building businesses and second homes in the city. Now a days when people say little Chicago they mainly refer to the East side of Hamilton which is over run with crime, Gang violence, and drugs. Where as the West side is often referred to as Hamiltucky.
Little Chicago is one of the last places I would want to live in Ohio, that and Cleveland.
Little Chicago by All things Ohio September 6, 2020
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West side of Chicago 

No - man’s land. A dirty war - zone. Advised to stay away from this area at all costs.
Yo ass live on the West Side of Chicago? Ew.

University of Chicago 

1. Ranked the 8th best overall university in the country by U.S. News and World Report.

2. The worst four years of your life.

3. The school that people in Korea know about but people in Chicago don't.

4. Not UIC (University of Illinois in Chicago)
Person 1: Where do you go to school?

Person 2: University of Chicago.

Person 1: Cool! I have a couple of friends that go there!

Person 2: No, you don't. It's U of C, not UIC.

Or,

Man 1: Is that a woman or a tree with warts?

Man 2: Impossible to tell, but she/it looks better than my
last girl friend from this school. Let's pop some more
anti-anxiety pills, smoke some weed, and drink a bit and see if she'll talk to us. Will you back me up in case I get scared?

Man 1: Please, does E=MC^2? Of course I'll back you up.

Man 2: Thanks, man. Hey, if this doesn't work out, let's go
home and study!

University of Chicago 

noun. The best school in America. Known for its rigorous curriculum, intelligent students, brilliant teachers and ugly females. The University of Chicago is better than all of the Ivies. Washington University in St. Louis thinks it compares with UofC but, thats just not factually correct. Usually, the smartest person you know goes to University of Chicago. Harvard is the UofC of the NE, Stanford of the West and Oxford of the European continent.
Student recently accepted into University of Chicago: Whew.

Student recently accepted into Yale: Why are you relieved shouldn't you be excited you go accepted into the University of Chicago?

Student recently accepted into University of Chicago: I'm relieved I don't have to go to Yale.
University of Chicago by de Facto February 28, 2010

oral chicago 

a sexual act also referred to as "deep dish" where a woman's sexual partner accepts her juices in his/her mouth and uses them to flavor a deep dish pizza or a hot dog
Andrew enjoyed giving Molly oral sex so much, he asked her if he could perform an oral chicago.
oral chicago by Big Donkey 16 November 12, 2013

judy chicago

I hooked up with that hairy-armed pink pussy hat wearing FemiNazi after the Antifa rally and she Judy Chicago’d so loud it woke up the dog.
judy chicago by Salohcin2 October 25, 2019

prairie(Chicago) 

Prairie
You hear someone say, “The neighbor kids love to play in the prairie,” and now you’re scratching your head and wondering where to find the Chicago prairie. Forget the images of Laurie Ingalls Wilder, log cabins and the tall prairie grass. When a Chicagoan refers to the prairie, he means a vacant lot in the neighborhood. The lot particularly fills the prairie title if it’s full of weeds, so if you squint and use your imagination, maybe you can see “prairie grass” in Chicago. Just don’t expect a Little House on the Prairie moment when you find one.
I just walked the dog over at the prairie(Chicago) and it was full of broken glass.
prairie(Chicago) by Keeboo April 7, 2021