20. Uptown

Location: Uptown

Former playground of prohibition-era mobsters (The Green Mill [4802 North Broadway St.], Al Capone's famous old haunt, is still considered Chicago's best place to catch some jazz), this North Side neighborhood enclave is now home to the city's densest population of Vietnamese and Korean food and culture. Get your Pho while getting your culture, too. Browsing this neighborhood offers some of Chicago's finest, oldest theaters, such as the Aragon, Riviera, and Uptown Theater.