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77.
If hell could freeze over, it would be Chicago. Horrible public transportation - CTA sucks, if moving there, I suggest you take a car. The weather is miserable, and not just the winters. Oh yeah, and check out the grey, endless flat landscape, inspiring isn't it?
Oh, and don't get me started on the local politics, corruption at its worst. Its most famous gangster, Al Capone, was actually from Brooklyn, moved to Chicago and realized how easy it would be to take advantage of its people.
After hearing so much about how great Chicago was from friends, I came to find out that none of them actually lived in the city. They all live in the fucking suburbs. Hmm, I wonder why?
I must say though, the only redeeming feature of that city is lake Michigan, but I'm sure if given the chance they'll find a way to screw that up too.

Rudyard Kipling on Chicago - "Having seen it, I urgently desire never to see it again."
by hell no! March 24, 2007
 
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