50
A awesome city located in Illinois. It has the world famous Sears Tower and it also has the Hancock building. Many people say it has many gangs, but it really doesn't. Chicago actually has the most nicest people.
John: Chicago has a lot of gangs!

Jeff: Have you ever even been to Chicago? There is barely any gangs and they have very nice people.
by ChicagoCitizen June 02, 2009
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51
the realest, truest city there is
where there is hella haters
where we say joe after every word
where we have bussas on every block
where we have a Pete's n harolds Chicken
where we ask for extra mild sauce
where we have grammer schools
the niggaz that rap don't just rap they tell a story
where the rawest projects stood up
where it's the most popular n most haters
where we come up with the best slang
where there is mostly blacks
this city is where people wish they were born so they hate cause they know the real ones stay duggie fresh
this is my city Chicago
there are hella haters in chicago
Other cities stay hatin on Chicago because of our slang and dance
by Ghetto Queen April 14, 2007
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52
Amazing world class city! Friendly dense urban center known as the Windy City, located in the American Midwest on the Great Lakes.

City that raised from the ashes (was totally destroyed in a great fire), and in testament of will/ability of mankind, Chicago was rebuilt, better taller wider and prouder, welcoming all opportunity to make self/community... Including world's first skyscrapers, first feats of pure brick, to innovative steel frames that have led to the boom of beautiful skyscrapers of great cities all around world!

Chicago's a busy hustling but friendly city with something for everyone! Good business/work opportunity (many fortune 500), relatively affordable cost of living, diverse restaurants, clubs/nightlife, family friendly parks/museums (Navy Pier, parks all along lake front), concerts (Lollapalooza, House of Blues, largest free music festival), Shopping (magnificent mile/Woodsfield mall), Sports lover's paradise (Cubs/Sox, Da Bears!, Bulls, Blackhawks etc)… Many diverse communities, from suburban to urban, all identify as "Chicago'ins"! There's many amazing cities, but no place quite like good old Chicago!
come on, baby don't cha wanna go, Back ta that same ol' place… sweet home Chicago!
by rext86 November 29, 2010
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53
An absolutely AMAZING city. If one is not from Chicago and wished to visit, I recommend staying in the North side. The North Side is an extremely nice place with plenty of entertainment and good food. However, if one should find themself in the South Side of Chicago, RUN FOR YOUR FUCKING LIFE!!! On my list of ghettos, I am officially declaring Chicago's South Side to be the fourth most dangerous ghetto in America.
Chicago's North Side is the complete opposite from it's South Side.
by Zuke July 12, 2006
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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
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Soft and offensive. Just like you.

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55
best city in the world: so much better than new york city
Chicago kicks New York's ass (mostly cuz chicago has ME! new york can never come close)
by chicagogirl415 August 02, 2011
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56
How an Assyrian Boater pronounces Chicago; a female in Chicago on the go
hi im new to chic-a-go. lookit at the chic-a-go
by Tena Love Less Zaia January 03, 2012
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