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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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