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. 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 largest free blues festival in the world, which takes place over three days and on five stages in both Grant Park and Millennium Park. The always-packed open-air festival has been headlined by blues legends such as B.B. King, Koko Taylor, and Buddy Guy.

    , Illinois, USA
  • 2. 404 Wine Bar


    Next door to the rowdy Diag Bar & Grill you'll find the serene 404 Wine Bar, a romantic spot filled with cozy nooks. The librarylike back room has ornate chandeliers, shelves lined with books, and dramatic oxblood walls. Grab a spot on the patio or near one of two fireplaces and enjoy a glass, flight, or bottle of wine accompanied by a cheese plate.

    2852 N. Southport Ave., Chicago, Illinois, 60687-4128, USA
  • 3. Apogee

    Near North Side

    Trendsetters hit the scene on the 26th floor of the Dana Hotel and Spa for cocktails with penthouse views or gravitate toward the fire pit on the patio.

    2 W. Erie St., Chicago, Illinois, 60654, USA
  • 4. Blokes & Birds

    Wrigleyville | Bars/Pubs

    A departure from the typical Wrigleyville sports bar, this modern public house draws Anglophiles thirsty for a well-poured pint and contemporary takes on classic English pub fare, such as shepherd's pie with stout-braised lamb and fish-and-chips with malt vinegar aioli. (The bar's name is British slang for "guys and girls.") Friday and Saturday nights, sing your heart out in its karaoke lounge.

    3343 N. Clark St., Chicago, Illinois, 60657, USA
  • 5. Blues Heaven Foundation

    South Loop

    For a walk into history, stop by the Blues Heaven Foundation, which occupies the former home of the legendary Chess Records. Breathe the same rarefied air as blues (and rock-and-roll) legends Muddy Waters, Howlin' Wolf, Chuck Berry, and the Rolling Stones, all of whom recorded here. Check out the Chess brothers' private offices, the recording studio, and the back stairway used only by signed musicians. Be sure to see the eerie "Life Cast Portraits" wall showcasing the plaster heads of the Chess recording artists. Tour hours are 12–4 Monday through Saturday.

    2120 S. Michigan Ave., Chicago, Illinois, 60616, USA
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  • 6. Booth One

    Old Town

    While new ownership restored the Ambassador name to this storied Gold Coast hotel in 2017, they lost the rights to call its historic restaurant the Pump Room. So they renamed the space in honor of its most coveted table, where celebrities and other VIPs have held court since the 1930s. The updated decor features numerous black-and-white photos of those famous faces, while the bar's classic cocktail and wine lists hope to lure a new generation of A-listers.

    1301 N. State Pkwy., Chicago, Illinois, 60610, USA
  • 7. Bridge House Tavern

    River North | Bars/Pubs

    With an enormous patio overlooking the Chicago River, this bar attracts both the after-work crowd and tourists searching for the quintessential city view. Order a burger or bratwurst and watch the boats docking barside. Off-season visitors can take refuge inside the cozy lounge with stone walls and wood paneling.

    321 N. Clark St., Chicago, Illinois, 60610, USA
  • 8. Bull & Bear

    River North | Bars/Pubs

    Bull & Bear amps up the testosterone, with a dual focus on sports—the bar's name references two Chicago sports teams—and the stock market. Reserve one of five booths with built-in beer taps (you pay by the ounce), or grab a seat at the bar and catch the game on one of several flat-screen TVs.

    431 N. Wells St., Chicago, Illinois, 60654, USA
  • 9. Chicago Improv Festival

    Comedy Clubs

    The springtime Chicago Improv Festival, the nation's largest festival for improvisers, has stages devoted to group, pair, and single improv; sketch comedy; and more.

    , Illinois, USA
  • 10. Circuit

    Lakeview | Bars/Pubs

    The biggest dance club in Boystown is a stripped-down hall energized by flashing lights, booming sounds, and a partying crowd. Take a break in the up-front martini bar.

    3641 N. Halsted St., Chicago, Illinois, 60657, USA
  • 11. Citizen Bar

    River North | Bars/Pubs

    Everyone's welcome at Citizen Bar, a sleek space with exposed brick walls and traditional bar fare. But the real draw is the huge, multilevel outdoor area—it's one of the city's most coveted spots come summer.

    364 W. Erie St., Chicago, Illinois, 60610, USA
  • 12. Debonair Social Club

    Wicker Park

    In the historic Flat Iron Building, the Debonair Social Club combines visual arts, music, and late-night dining. Upstairs, curated video installations line the walls surrounding the stage-cum–dance floor; the dimly lighted downstairs has a more clandestine feel.

    1575 N. Milwaukee Ave., Chicago, Illinois, 60622, USA
  • 13. Division Street


    For vestiges of the old Rush Street, continue north to Division Street, between Clark and State. The watering holes here are crowded and noisy, and the clientele consists mostly of suburbanites and out-of-towners on the make. Among the better-known singles' bars are Butch McGuire's, the Lodge, and Original Mother's.

    Chicago, Illinois, USA
  • 14. Double Door

    Wicker Park | Live Music

    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 Rolling Stones shows have been held here. Door No. 3, a lounge with a speakeasy theme, occupies the basement.

    1572 N. Milwaukee Ave., Chicago, Illinois, 60622, USA
  • 15. East Room

    Logan Square

    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. Inside, the lights are dim, the drinks (cash only) are cheap, and the whiskey choices are plentiful. DJs spin funk, house, and other genres; seek out the decked-out elevator room for the best seat in the house.

    2354 N. Milwaukee Ave., Chicago, Illinois, 60647, USA
  • 16. Elbo Room


    Elbo Room, a multilevel space in an elbow-shape corner building, has a basement rec-room feel. Talented live bands add a strong dose of nu-jazz, funk, soul, pop, and rock seven days a week.

    2871 N. Lincoln Ave., Chicago, Illinois, 60657, USA
  • 17. Happy Village

    Ukrainian Village

    Located in Ukrainian Village, this neighborhood institution is known for its cheap beer, Ping Pong tables, and, when the weather cooperates, its massive beer garden. There’s no kitchen, but Chicago’s own “tamale guy,” who sells authentic Mexican tamales out of a cooler, swings by nightly. Be sure to hit an ATM before you arrive because Happy Village is cash-only.

    1059 N. Wolcott Ave., Chicago, Illinois, 60622, USA
  • 18. Joie de Vine

    Far North Side

    Catering to a lesbian clientele, this wine bar has expanded its focus to include craft beer and cocktails. The space itself is cozy, but good design (and sidewalk tables in summer) keeps it from feeling claustrophobic. Sit at the long wooden bar or opposing banquette and enjoy the room's real focal point, a glass-brick wall lighted up in multiple colors.

    1744 W. Balmoral Ave., Chicago, Illinois, 60640, USA
  • 19. Logan Square Auditorium

    Logan Square

    The second-floor ballroom hosts all-ages rock shows put on by the team at the Empty Bottle, plus other live performances and assorted special events. The acoustics aren't the best, but the hip younger crowd it draws doesn't seem to care. For those 21 and over, there's a full bar.

    2539 N. Kedzie Blvd., Chicago, Illinois, 60647, USA
  • 20. Lollapalooza

    Live Music

    The current incarnation of Perry Farrell’s famed festival takes over Grant Park for three days in August. Lollapalooza boasts a packed slate of big-name musicians (past editions have included the Red Hot Chili Peppers, Kanye West, Lady Gaga, and Pearl Jam). Tickets typically sell out before the lineup is even announced, but many turn up on Craigslist and third-party websites in the days leading up to the event.

    , Illinois, USA

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