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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  • 21. Nick's Beer Garden

    Wicker Park

    Nick's Beer Garden is a neighborhood favorite, especially in the wee hours (it's open until 4 am; 5 am Saturday). Kitschy tropical decor—think palm trees, flamingos, and a surfboard—adds to the appeal.

    1516 N. Milwaukee Ave., Chicago, Illinois, 60610, USA
    773-252–1155
  • 22. Northside Bar & Grill

    Wicker Park

    This spot was one of the first anchors of the now-teeming Wicker Park nightlife scene. Locals come to drink, eat, shoot pool, and see and be seen. The enclosed indoor-outdoor patio lets you get the best out of the chancy Chicago weather.

    1635 N. Damen Ave., Chicago, Illinois, 60647, USA
    773-384–3555
  • 23. Pitchfork Music Festival

    Live Music

    This three-day indie-oriented festival brings a diverse array of top and emerging talent to Union Park each July. Although smaller than Lollapalooza (it has three stages compared to eight-plus), devotees say the acts are more eclectic and the environment more comfortable. Artists including Beck, Kendrick Lamar, The National, and St. Vincent have played Pitchfork.

    , Illinois, USA
    312-746–5494
  • 24. Rockit Bar & Grill

    River North | Bars/Pubs

    Designer Nate Berkus assembled Rockit's hunter-lodge look: picture wood-plank-framed plasma TVs, antler chandeliers, and brown-leather booths. The crowd, much like the beer list, is diverse and tasteful, and there's a good mix of men and women despite the masculine vibe. Dress to impress.

    22 W. Hubbard St., Chicago, Illinois, 60610, USA
    312-645–6000
  • 25. Rodan

    Wicker Park | Bars/Pubs

    The highly stylized Rodan is a restaurant and lounge that caters mostly to the young neighborhood hipsters who arrive at dinnertime (served until 11 pm) and stay put until closing. The narrow space often feels cramped, but if you can snag a spot at the bar or on a blue-suede banquette, an evening of major-league people-watching is in store. Snacks are served all night, so refuel with a pile of wasabi-tempura fries served with a side of siracha ketchup.

    1530 N. Milwaukee Ave., Chicago, Illinois, 60622, USA
    773-276–7036
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  • 26. Rush Street

    Bars/Pubs

    The famous Chicago bar scene known as Rush Street has faded into the mists of time, although the street has found resurgent energy with the opening of a string of upscale restaurants and outdoor cafés.

    Chicago, Illinois, USA
  • 27. The Abbey Pub

    Irving Park | Live Music

    Located in the Irving Park neighborhood, about 15 minutes northwest of downtown, this place showcases rock, as well as some Irish, Celtic, and country music, in a large concert hall with a separate, busy pub. By day the hall is used to show soccer and rugby games from the United Kingdom and Ireland.

    3420 W. Grace St., Chicago, Illinois, 60618, USA
    773-478–4408
  • 28. The Burlington

    Logan Square

    Just a few blocks from the heart of Logan Square, this narrow bar has a woodsy vibe and a straightforward menu. In the front room, a rotating roster of DJs plays an eclectic mix of tunes; in the back room, live music from both local and touring acts tends to skew toward punk or noise rock.

    3425 W. Fullerton Ave., Chicago, Illinois, 60647, USA
    773-384–3243
  • 29. The California Clipper Lounge

    Humboldt Park

    After being spruced up by Brendan Sodikoff, one of Chicago's best-known restaurateurs, this 1930s lounge is better than ever. A curving 60-foot-long Brunswick bar still dominates the interior, and tiny booths still line the long room back-to-back like seats on a train. But the look is now cleaner, and the cocktail list is longer (most cost $11 or less, so prices are refreshingly old-school). A tobacco shop has been added in the back room, too. Beloved by hipsters who've begun gentrifying the surrounding neighborhood, the lounge is located in Humboldt Park, just west of Wicker Park.

    1002 N. California Ave., Chicago, Illinois, 60622, USA
    773-384–2547
  • 30. The Motel Bar

    River North | Bars/Pubs

    The Motel Bar has all the comforts of a real, honest-to-goodness motel bar (TVs tuned to sports, classic cocktails, and a retro color scheme), but the atmosphere is amped-up with sexy, low-rise furniture and a "room service" menu of upscale bites.

    600 W. Chicago Ave., Chicago, Illinois, 60610, USA
    312-822–2900
  • 31. The Whistler

    Logan Square

    If you love unusual cocktails, free live music, and a laid-back vibe, the Whistler is the bar for you. It can get crowded, but the potent and creative drinks will make you forget any time spent waiting in line. These days the cocktail list changes daily; check @whistlermenu on Instagram for the latest update.

    2421 N. Milwaukee Ave., Chicago, Illinois, 60647, USA
    773-227–3530
  • 32. Transit

    West Loop | Dance Club

    Despite being hidden away underneath the El tracks in a spooky stretch west of downtown, Transit is wildly popular with young clubgoers. Inside, the multiroom space has a crisp design and sumptuous VIP area. Don't miss the glowing black-and-white bar between the oval and chandelier rooms, or the mezzanine with its minimalist furniture and oversize mahogany table.

    1431 W. Lake St., Chicago, Illinois, 60607, USA
    312-491–8600

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