A pretty cool city. Better than the shithole(New York). A lot like another great city, Boston(which is the best in my opinion). Also, people from there aren't all arrogant assholes like New Yorker's are.
by AflacJack August 13, 2003
an 80s band that played both heart wrenching break-up songs and songs that almost guarantee sex. ex we can last forever and stay the night.
girl to friend's : I didn't want to at first but then he played some chicago and and I could not controll myself.
by lurrrrrrrrrrrrrrrrrrrrrrrrrrrr August 20, 2011
A) The metropolitan capital of the state of Illonois. Known also as the "Windy City." Chicago is the third-largest city in the U.S., and the largest inland city in the country.

B) A game played while smoking the sacred herb whereby an individual who is smoking holds in his hit until the joint/blunt/pipe/bub/bong has been passed all the way around the circle and back to said individual. Then, and only then, can he exhale his hit and take another.
A) Chicago is a pretty cool city, you should check it out.
B) Dude, let's play chicago with that joint and get lifted outta our skulls!
by IAmHydrogen August 10, 2005
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
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
A lot of people want to come to this city but most of the people who love here want to leave this city.

Chicago is one of the most deadliest city's in America. This city will change your life in 1 day, and if you make it a another day it's because a bullet hit someone else.
They pull a knife, you pull a gun. He sends one of yours to the hospital, you send one of his to the morgue. *That’s* the *Chicago* way
by Stinkkay May 07, 2016
I dunno who thinks Chicago is pronounced the way it is here , but they obviously aren't from the City in a Garden. Yeah, many people pronounce it "Chi-cah-go," now. But if you are a white ethnic of a certain age or neighborhood the correct way to say it is "Chi-caw-go." Watch old movies from the 30s and 40s and you'll see that was the way it was spoken. I blame the New York based radio and TV media convincing the world that it is "Chi-cah-go." If you wanna talk like a real neighborhood Chicawgoan make an "s" sound at the end of plurals, don't use the "z" sound.
Hey you guyss, wanna go to the Chicago Bearss game on Sunnay?
by Steddy Eddy April 25, 2016
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