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85.
If you're not from the hood then you don't belong in this city. Home of some of the most notorious gangs in america such as the Vice Lords, Gangsta Disciples and much much more. I think this city can hang with Dallas and Houston(only if we were on their turf, other than that they can't hang)
Chicago is the city to be if you're from the hood, ghetto, and/or projects and you are looking for more.
by *Wonderboy Marvel* July 08, 2003
 
86.
An overrated rat hole of a city in the Midwest U.S., with buildings as overbearing as the people, annoying traffic jams, mediocre food, and a "same shit different block" nightlife. Terrible schools. Over-glorified sports teams. BAD SMELLS around town. Lots of racial tension due to the urban rednecks who inhabit 80% of the city. Lot's of crime all around town. Corrupt politicians, still to this day. A decent looking city wasted on fat pompous asses and wannabe toughguys, like most of those knobs who wrote the previous definitions.
Chicago is the New York of the Midwest, and that's not a good thing !
by Stevie Bartman March 14, 2007
 
87.
City with a ridiculous and morally backwards culture, that has an overwhelmingly large amount of ignorant, narrow-minded, and racist people.

If you are colored, the white people won't treat you for who you are, but for what you are. Many of them are malicious in this sense, and enjoy the feeling and benefit of feeling superior to those they look down on, and sometimes wish to mistreat. Many white people (men especially) feel uncomfortable around colored people whose personalities do not fit within their knowledge of ignorant stereotypes, and have the tendency or desire to put down, intimidate, or mistreat a colored man who is confident, intelligent, and most importantly charismatic. If you are a colored woman, you are "allowed" to be a person, and assert an individuality, without it being rejected, because the white men do not feel threatened by colored females, and rather see them as desirable.

Nonetheless there is to this day an overwhelming amount of people who, pathetically, are still unused to or unfamiliar with the notion of colored people being people, and who still feel uncomfortable when a colored person enters the same restaurant, sits or stands nearby, offers their opinion, asserts their personality, or in general, is present. Perhaps they don't feel that colored people should have the same freedom to enjoy life. It is a sad example of the cultural denial of freedom and democracy in a modern American city.

If you really think this is untrue then take the time to stop and observe the world around you.
If you don't like an ignorant, narrow-minded and racist society, don't go to Chicago. This, is why New York is better.
by American Eye April 23, 2006
 
88.
A city with too much ego for too little reason. Prone to comparing itself to New York ALL THE TIME, God only knows why. A city that claims to be very cultural but fails to fully support local artists and art scenes. A city that is too spread out, too ethnically divided, too good at hiding its poor, and too proud of it's famous el system to recognize that it is grossly inadequate compared to other cities (like NYC). A city of passive aggressiveness.
That woman with her hood on my rear bumper is acting like its my fault there traffic isn't moving. She acts like she's from Chicago.
by Dee February 19, 2005
 
89.
(N.) a would-be okay town, if not responsible for Jerry Springer, Oprah's book club, Perfect Strangers, and God-awful movies from broadway with it's name as the title. (Oh yeah, and that too, broadway.)
I'm from the big, windy city. shi-town, illinois. I'm the reason why musicals are back. Horray for me!
by G-Union May 16, 2003
 
90.
The Sears Tower is the architectural equivalent of a stack of boxes with cockroach antennae. No one cares that it's tall.
That is, no one outside of Chicago cares that it's tall.
by shitcago March 12, 2005
 
91.
The whole damn city is ghetto expect for the northside and Downtown. Its like a mini New York City.
It's a desent city. View is better from hancock building then, Sears Tower and don't let anyone tell you anything different.
by Taji July 25, 2004