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1.
A resident who lives or was born in Chicago. They are very proud of their city, which is a beautiful one. Sometimes they will try to compare it to the greatest city in the world (New York City) which is unacceptable.
Chicagoan: Chicago is the best city in the world and New york city is not

Chinese people: oh new york!!! I love nyc, but what the fuck is a "chicago"?

Indian: Yea, I never heard of a "Chicago" before, but I'd love to visit new york!
by healthy carrot <<< was bored July 10, 2008
 
2.
A person from the city of Chicago.
I had great sex with a hot female Chicagoan.
by brahm2 October 15, 2003
 
3.
An overbearing, usually quite overweight, pompous citizen who hails from the armpit of the Midwest-Chicago Illinois. Interests include getting drunk, using drugs, watching meaningless baseball, watching meaningless football, and dating transvestites from Wrigleyville.
That Chicagoan sure does like to boast about their crappy overrated town!
by Stevie Bartman March 14, 2007
 
4.
a person from the spectacular city of Chicago. A resident. Someone who knows how to party , work , and enjoy skyscrapers.
chicagoans come from chicago(aka chitown)
by chicago nikki February 13, 2005
 
5.
A true Chicagoan : lives in the city, Is not stuck up, and puts mayo and hot sauce on the elotes sold at the street corner.....A suburbanites are clueless as to what the elotes man with the cart is selling. They are always bad mouthing the city but cheer for the Chicago teams and say they are from Chicago when they go to other parts of the country/world.
The man in the suit with the fancy expensive watch standing on the L platform was obviously not a Chicagoan.
by Johnny Chicago Dillinger February 10, 2011