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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.
I. "Who Sane" Myarsによって 2010年09月06日(月)
1254 46
 
2.
what rappers and black people call Chicago
Shytown is the shit my nigga
JDogによって 2005年04月02日(土)
155 156
 
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.
Roquenによって 2011年05月07日(土)
46 48
 
4.
a city in chigao where all the ghetto ppl live
Guy: where u reppin B?
Guy2: Shy-Town!
OLAによって 2005年07月11日(月)
148 151
 
5.
a city/hometown, in America
a baller from shy town
Kristiによって 2004年10月19日(火)
115 120
 
6.
the flyest new band in hollywood
what you doin tonight?

checkin out shytown at the mint

tight.
music loveによって 2009年04月11日(土)
80 122
 
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...
Charm and Strangeによって 2010年04月05日(月)
9 99