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10Best's Chicago Nightlife

Bootleg liquor, improv jazz, and gorgeous dames in flappers. Prohibition Era Chi-Town was legendary for its underground speakeasies. Today’s scene is more on the up-and-up – an electrifying nightscape that holds its own against any in the world. Within walking distance of Wrigley Field’s cozy confines are busy sports bars and pubs, headlined by immortal Murphy’s Bleacher’s and Old World-style Irish Oak Pub. For swankier environs, look to River North and the Magnificent Mile, where you’ll find Harry’s Velvet Room on West Illinois, Hellenic-themed Narcisse, and other such young and trendy enclaves. When it’s time to pop the big question, there are few better places than the Hancock Building’s Signature Lounge, a sophisticated, 96th-floor aerie that overlooks the restaurant below and offers a spectacular panorama of the Chicago skyline. Of course, no visit is complete without sampling live blues at a dingy, smoky legend like B.L.U.E.S. on North Halsted, where folks like Big Jack Johnson and Magic Slim have thrilled crowds deep into the Windy City night.