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54.
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
 
1.
Best damn city in the world!
Chicago rocks hard, yo!
by some dude December 28, 2004
 
2.
Truly one of the greatest cities in the entire nation. With a total population exceeding 2.9 million inside the city limits alone, multiple cultures and ethnicities, cool-sounding urban, midwestern nasal accents (see ear candy), a rich history, tons of museums, theaters, arcades, the Brookfield Zoo; the best pizza outside of New York City, and probably one of the best city skylines in the United States, Chicago has something to offer to everyone. It is a higher standard of a metropolis that all other American cities strive to be like(and many of them have succeeded in that: see Cincinnati, Philadelphia, Detroit, Atlanta, DC, Denver, Omaha, and Seattle.
Chicago is the ultimate economic, cultural, educational, business, entertainment, industrial, and population center of the Midwest.
by Republican Warrior March 29, 2005
 
3.
One of the most, if not the most, beautiful cities in the US.
"Chicago is the Verona of America," (spoken with an Italian accent).
by Max Moriarty June 28, 2005
 
4.
Big city with a beautiful skyline. Although geographically placed in the Midwestern state of Illinois, it should be considered it's own state since the rest of the midwest is filled with drunk redneck republicans.
"So your from Illinois?"
"No-I'm from Chicago"
by Laur December 10, 2004
 
5.
hottest city alive, i live there
go to chicago muh fucka
by orielah February 25, 2005
 
6.
If you keep saying that only gangs are from there, you have better been all over the damn city.
Chicago rules fuckers.
by Adrian Herrera January 08, 2005
 
7.
one kickass town, home of the sears tower, hancock building, the navy pier, kapone, some kickass rappers like twista. If you can't hang here, don't bother trying. I live in the 'burbs though, but i've been therre plenty of times.
Chicago Kicks Ass
by mr. johnny March 05, 2004