32 Best Nightlife in Chicago, Illinois

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.