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7.
The wrong way to spell Chi-Town, which is a nickname for Chicago, Illinois, and has nothing to do with "shy"ness at all.

Only tourists spell it Shy-Town, and it's really annoying to have to correct.
Tourist: I'm going to stop in Shy-Town on my trip!
Chicagoan: Good Lord, not another one...
av Charm and Strange 5 april 2010
 
1.
a. From an acronym for Chicago, i.e., "Shit-Headed Yahoo Town."

b. A term of derision for a lunatic city that deserves every whit for giving America an unrivaled gaggle of thieves, murderers, perverts, gangsters, hoodlums, thugs, corrupt politicians and assorted societal misfits that boggles the mind.

c. A town teeming with Shit-Headed Yahoos who continually vote for the dregs of themselves to run the government.

d. A term hated by actual SHY Chicagoans who try to redeem their reputation by insisting "SHY" really means "chi" (actually a Chinese word and Greek letter) and insist it is used only by non-Chicagoans (which is generally true).
Why da' Shy Town hood pimpz voted fo' da' B-Ho? Ya'll is mad stupid.
av I. "Who Sane" Myars 6 september 2010
 
2.
what rappers and black people call Chicago
Shytown is the shit my nigga
av JDog 2 april 2005
 
3.
A nickname for Chicago, IL (USA) made popular by pop-music. Dissected by removing "cago" from the word and replacing the last half with words for communities. Such as: Chi-Town, Chi-City, Chi-Hood, etc

other nicknames for Chicago are in the Tags
I am going to visit my cousin in shytown.
av Roquen 7 maj 2011
 
4.
a city in chigao where all the ghetto ppl live
Guy: where u reppin B?
Guy2: Shy-Town!
av OLA 11 juli 2005
 
5.
a city/hometown, in America
a baller from shy town
av Kristi 19 oktober 2004
 
6.
the flyest new band in hollywood
what you doin tonight?

checkin out shytown at the mint

tight.
av music love 11 april 2009