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. Berlin Nightclub

    Lakeview | Dance Clubs

    A multicultural, pansexual dance club near the Belmont El station, Berlin has progressive electronic dance music and fun themed nights (Madonna...Read More

  • 2. Big Chicks

    Far North Side | Bars/Pubs

    In the Uptown area of the Far North Side, Big Chicks is a striking alternative to the Halsted strip, with a funky crowd that appreciates the...Read More

  • 3. Buddy Guy's Legends

    South Loop | Live Music

    Relocated from its original location a few doors down, Buddy Guy's Legends has a superb sound system, excellent sightlines, and more space to...Read More

  • 4. Chicago Blues Festival

    Live Music

    The Chicago Blues Festival leaves no doubt about it: Chicago still loves to sing the blues. Each June, the city pulses with sounds from the...Read More

  • 5. Gilt Bar

    River North | Bars/Pubs

    Vintage furnishings and cocktails like the Bee's Knees (gin, lemon, and honey) set the 1920s speakeasy scene at this low-lighted lounge. The...Read More

  • 6. Green Mill Cocktail Lounge

    Far North Side | Live Music

    A Chicago institution, the Green Mill in not-so-trendy Uptown has been around since 1907. Deep leather banquettes and ornate wood paneling line...Read More

  • 7. Hopleaf

    Far North Side | Bars/Pubs

    An anchor in the Andersonville corridor, Hopleaf continues the tradition of the classic Chicago bar hospitable to conversation (there's not...Read More

  • 8. House of Blues

    River North | Live Music

    Though its name implies otherwise, House of Blues actually attracts big-name performers of all genres, including jazz, roots, gospel, alternative...Read More

  • 9. Old Town Ale House

    Near North | Bars/Pubs

    Just a stone's throw from Second City, Old Town Ale House has attracted a diverse cast of characters since it opened in 1958, including comedy...Read More

  • 10. Old Town School of Folk Music

    Lincoln Square | Live Music

    Chicago's oldest folk-music school has served as folk central in the city since it opened in 1957. The welcoming spot in Lincoln Square hosts...Read More

  • 11. Rosa's Lounge

    Logan Square | Live Music

    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

  • 12. Second City

    Near North | Comedy Clubs

    An institution since 1959, Second City has served as a launching pad for some of the hottest comedians around. Alumni include Dan Aykroyd, Tina...Read More

  • 13. Signature Lounge

    Near North | Bars/Pubs

    When it comes to views, the Signature Lounge has no competition. Perched on the 96th floor of the John Hancock Center—above even the tower's...Read More

  • 14. Simon's Tavern

    Andersonville | Bars/Pubs

    This classic Andersonville bar honors the neighborhood’s Swedish roots with its signature drink, glögg —mulled Swedish wine, served hot in...Read More

  • 15. The Annoyance Theatre & Bar

    Lakeview | Comedy Clubs

    This is home base for Annoyance Productions, an irreverent group best known for hits like Skinprov and Hitch*Cocktails . ...Read More

  • 16. The Empty Bottle

    Wicker Park | Live Music

    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

  • 17. The Hideout

    Bucktown | Live Music

    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

  • 18. 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

  • 19. 3rd Coast Cafe & Wine Bar

    Near North | Cafés

    The oldest coffeehouse in the Gold Coast pleases just about everyone with a full menu served until midnight seven nights a week. The inviting...Read More

  • 20. 404 Wine Bar

    Lakeview | Wine Bars

    Enter through rowdy Jack's Bar & Grill to find the serene 404 Wine Bar, a romantic spot filled with cozy nooks. The librarylike back room...Read More

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