Chicago

Chicago's entertainment varies from loud and loose to sophisticated and sedate. You'll find classic Chicago corner bars in most neighborhoods, along with trendier alternatives like wine bars and lounges. The strains of blues and jazz provide much of the backbeat to the city's groove, and an alternative country scene is flourishing. As far as dancing is concerned, take your pick from cavernous clubs to smaller spots with DJs spinning dance tunes; there's everything from hip-hop to swing. Wicker Park/Bucktown and River North have the hottest nightlife, but prime spots are spread throughout the city.

Shows usually begin at 9 pm; cover charges generally range from $3 to $20, depending on the day of the week (Friday and Saturday nights are the most expensive). The list of blues and jazz clubs includes several South Side locations: be cautious about transportation here late at night, because some of these neighborhoods can be unsafe. Drive your own car or ask the bartender to call you a cab.

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  • 1. Rosa's Lounge

    Logan Square | Music Clubs

    On a given night at Rosa's Lounge, near Bucktown, you'll find Tony, the owner, working the crowd, and his mother, Rosa, behind the bar. What...Read More

  • 2. The Empty Bottle

    Wicker Park | Music Clubs

    This place, in the Ukrainian Village near Wicker Park, may have toys and knickknacks around the bar (including a case of macabre baby-doll heads...Read More

  • 3. The Hideout

    Bucktown | Music Clubs

    The Hideout, which is literally hidden away in a North Side industrial zone, has managed to make country music hip in Chicago. Players on the...Read More

  • 4. The Matchbox

    Wicker Park | Bars/Pubs

    In West Town near Wicker Park, the Matchbox isn't much bigger than a you-know-what, but the hodgepodge of regulars don't seem to mind. In fact...Read More

  • 5. B.L.U.E.S

    Lincoln Park | Music Clubs

    The best thing about B.L.U.E.S. is that there isn't a bad seat in the joint. The worst thing? The crowds—come early if you want to score a seat...Read More

  • 6. Davenport's Piano Bar & Cabaret

    Wicker Park | Piano Bars/Lounges

    Davenport's, a sophisticated cabaret booking both local and touring acts, brings a grown-up presence to the Wicker Park club scene. The piano...Read More

  • 7. Debonair Social Club

    Bucktown | Bars/Pubs

    In the historic Flat Iron Building, the Debonair Social Club combines visual arts, music, and late-night dining. Upstairs, curated video...Read More

  • 8. Delilah's

    Lincoln Park | Bars/Pubs

    A rare dive bar amid Lincoln Park's tonier establishments, Delilah's is dark and a bit grungy. But the bar has a friendly, unpretentious vibe...Read More

  • 9. Double Door

    Wicker Park | Music Clubs

    Double Door is a hotbed for music in Wicker Park. The large bar books up-and-coming local and national acts from rock to acid jazz. Unannounced...Read More

  • 10. East Room

    Logan Square | Bars/Pubs

    This unmarked "secret" bar carries through with its speakeasy theme—the only sign you’re in the right place is the red light above the door...Read More

  • 11. Emporium Arcade Bar

    Wicker Park | Bars/Pubs

    Two of America’s favorite pastimes—drinking and playing classic arcade games—come together here. You can do both affordably, too. Most games...Read More

  • 12. FitzGerald's Nightclub

    Music Clubs

    Although it's a 30-minute schlep west of Chicago, FitzGerald's draws crowds from all over the city and suburbs with its mix of folk, jazz, blues...Read More

  • 13. Gamekeepers

    Lincoln Park | Bars/Pubs

    Full of sports fans and former frat boys, Gamekeepers has more than 40 TVs, three projection screens, and complete satellite sports coverage...Read More

  • 14. Happy Village

    Ukrainian Village/Wicker Park | Brewpubs/Beer Gardens

    Located in Ukrainian Village, this neighborhood institution is known for its cheap beer, Ping Pong tables, and, when the weather cooperates...Read More

  • 15. Hi-Tops

    Lincoln Park | Bars/Pubs

    Hi-Tops may be the ultimate sports bar. Multiple flat-screen TVs, a lively crowd, and solid bar food keep sports fans coming. ...Read More

  • 16. I.O.

    Lincoln Park | Comedy Clubs

    Formerly called ImprovOlympic, I.O. is the city's home for long-form improvisation. The signature piece is "The Harold," in which a team of...Read More

  • 17. Kincade's

    Lincoln Park | Bars/Pubs

    Popular Kincade's packs 'em in on two levels with a 10-foot-wide video monitor, several plasma screens, and a bar menu that invites patrons...Read More

  • 18. Kingston Mines

    Lincoln Park | Music Clubs

    In 1968, Kingston Mines went down in Chicago history as the first blues club to open on the North Side. Though it's since moved to bigger digs...Read More

  • 19. Late Bar

    Bars/Pubs

    Enjoy late-night music and potent martinis? Late Bar, located along a somewhat lonely stretch of Belmont Avenue, is the place for you. The best...Read More

  • 20. Lincoln Hall

    Lincoln Park | Music Clubs

    The owners of Lincoln Hall transformed a former movie theater into an intimate concert space with great sight lines, an excellent sound system...Read More

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