3rd largest city in america,16th Richest city in the world. New multi-million dollar pent houses and condos being built(see Chicago spire & waldrof astoria) milwaukee has some odd complex with chicago but cant compete (milwaukees lame dont ever go thier!!!) saw its far share of crime and population loss during the 80's an 90s but is on the rise again. I would say a cleaner version of new york, downtown is never dead, u can go at 3:00am and still have fun. 24 hour city with the most agressive drivers i have ever seen( and im from boston)World Class shoipping just to name a few, Prada, louis vitton,gucci,hugo boss,fendi,and more..big city lots of fun and great pizza and hot dogs,nice historic homes brown stones huge victorian homes on the south side, 24 hour rail system and bus. (No more Projects!!!) good clubs,great bars,nice homes go to chicago and i'll graruntee you will love it.
Milwaukeean: i hate chiago drivers
Chicagoan: well thats because your drunk,dumb and from wisconsin
Milwaukeean: o we wish we were you!
by Move out the way! December 20, 2008

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A city in the state of Illinois. It is the largest city in Illinois, the largest in the Midwest, and the third largest in the United States. A very impressive skyline, and home to many fortune 500 companies. Although parts of the city are impoverished, what city DOESN'T have places like that? The most expensive inland city in the US. Upscale areas by far dominate the low scale areas. One of the best cities in the country, and in the world. Extremely diverse, although many people believe Chicago is segregated still because of it's past. If you haven't been there before, please stfu like you actually know something.
Chicago has something for everyone.
by DONOVANN November 03, 2006

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A very large city in the North of Illinois filled with pretentious douchebags who think they are far superior to anyone downstate, and that anything south of the suburbs is redneck country. Although the city itself features many famous attractions and great restaurants (and starbucks on every fucking corner), the people sort of counteract all this appeal. I was actually asked for directions while visiting there, the people inquiring were incredibly shocked to learn I was from central Illinois, wondering about my lack of redneck-ness. I mean, it's a great city, if you don't ever want to see trees and love to be stuck-up.
Chicago guy: Hey where do you live around here?
me: Oh, no I'm from Springfield.
Chicago guy: hmm.. Springfield? Never heard of it.
me: It's the capitol you fucktard.
Chicago guy: Whatever, don't you have a farm to get back to?
me: *knocks him the fuck out*
by sethisto28 August 15, 2011

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Chicaco is the one city i call home. The best city in the US. With a population of nearly 3 million, but on friday nights.. it becomes ricer nation. I would say that approximately 150 Honda Civics with 9 inch mufflers show up to the street races. Although they range from color and trim...its all the same. A very high pitched noise comes from them and the NITTO stickers add 25 horses to them...its entertaining seeing them, but it wont compare to LA or any city with real cars!
1: Are you going to the chicago races tonight?
2: Yea im gonna take my Civic. Oh do you know mike just got a civic
1: cool so did i and jake
by Juize22 June 08, 2007

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When there are two joints or blunts in a circle of friends; one is passed clockwise, the other counterclockwise. When two arrive at your doorstep you have to "chicago;" hit both of them simultaneously, preferably in the manner of inserting each between two different sets of knuckles of the same hand, making a chamber with your fist and inhaling deeply through the pipe created by your thumb and forefinger.
Yo, bitch, you just got hit. CHICAGO!
by transcendental fusion February 05, 2011

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a game where you hold your "reefer" smoke in your lungs till the joint gets back to you.
lets do chicago with this "j"
by Taz February 25, 2004

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The act of dragging out a story.
Scott is constantly pulling a Chicago. When he tells a story he talks about the weather in Illinois but all we really need to know is where the best pizza place is in Chicago.
by daisieNC May 27, 2010

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