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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.
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 owner's art collection hanging on the walls. The fun-loving staff and their self-selected eclectic music are the payoffs for the hike to get here. Special attractions include weekend dancing and free Sunday-afternoon buffets.
Relocated from its original location a few doors down, Buddy Guy's Legends has a superb sound system, excellent sightlines, and more space to showcase Grammy Award–winning blues performer/owner Buddy Guy's collection of blues memorabilia. Look for local blues acts during the week and larger-scale touring acts on weekends. Don't miss Buddy Guy in January, when he performs a monthlong home stand of shows (tickets go on sale one month in advance). There's also a substantial menu of Cajun and Creole favorites.
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.
Vintage furnishings, upholstered walls, and intriguing details set the 1920s speakeasy scene at this low-lighted lounge. Downstairs, The Library has velvet booths and vintage art surrounding a handsome book-lined bar.
A Chicago institution, the Green Mill has stood sentinel in the Uptown neighborhood since 1907. Deep leather banquettes and ornate wood paneling line the walls, and a photo of former patron Al Capone occupies a place of honor on the piano behind the bar. The jazz entertainment is both excellent and contemporary—the club launched the careers of Kurt Elling and Patricia Barber.
An anchor in the Andersonville corridor, Hopleaf continues the tradition of the classic Chicago bar hospitable to conversation (there's not a TV in sight). The lengthy beer menu emphasizes Belgian varieties and regional microbrews, and the Belgian fare served here far surpasses typical bar food. Don't miss the ale-steamed mussels and delectable skinny fries with aioli on the side.
Though its name implies otherwise, House of Blues actually attracts big-name performers of all genres, including jazz, roots, gospel, alternative rock, hip-hop, world, and R&B. The interior is an elaborate cross between blues bar and ornate opera house. Its restaurant has a satisfying Sunday gospel brunch. Part of the Marina City complex, its entrance is on State Street.
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 legends John Belushi and Bill Murray. With eclectic artwork, a mural of bar denizens painted in the '70s, and an on-site lending library, it's a dingy neighborhood bar unlike any other in the city—perhaps the country. Esteemed film critic Roger Ebert called it "the best bar in the world."
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 outstanding performances by national and local acts in an intimate-feeling 420-seat concert hall that has excellent acoustics. A major expansion in 2012 added a new, environmentally friendly facility across the street, with a 150-seat performance hall and acoustically engineered classrooms.
On a given night at Rosa's Lounge, near Bucktown, you'll find Tony, the owner, working the crowd. What makes the club special is that he moved here from Italy out of a pure love for the blues. Stop by and partake in Rosa's winning mixture of big-name and local talent, stiff drinks, and friendly service—the same since it opened in 1984.
The epicenter of comedy since 1959, The Second City has launched the careers of countless comedy legends. Alumni include Bill Murray, Catherine O’Hara, Stephen Colbert, Tina Fey, and Keegan-Michael Key. The revues on the company's historic Mainstage and more intimate e.t.c. space are fully realized sketch comedy shows, but the prescripted material is developed through improvisation in front of audiences. There’s always plenty of time in each show devoted to demonstrating the comedy chops of the quick-witted performers. Most nights, a free improv set after the late show features cast members and invited guests (sometimes famous, sometimes not). UP Comedy Club presents award-winning touring shows, comedy festivals, and special guest performances. In Donny's Skybox upstairs, you're likely to see one of Chicago's many fledgling improv comedy troupes debuting fresh material.
This is home base for Annoyance Productions, an irreverent group best known for hits like Skinprov and Hitch*Cocktails.
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), but when it comes to booking rock, punk, and jazz bands from the indie scene, it's a serious place with no pretensions. Grab some grub next door at Pizza Friendly Pizza before the show—the thick Sicilian-style squares, created in collaboration with fine dining vet Noah Sandoval, are among the best pizza bets in the whole city.
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 city's alternative country scene have adopted the friendly hole-in-the-wall, and bands ranging from the obscure to the semifamous take the stage. Late night DJ sets, standup, trivia, and even a music-theme talk show round out the entertainment offerings.
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, many claim it's the dark, cramped quarters (we're talking 3 feet wide at its narrowest) that keep them coming back. A heated front patio comes in handy when you need to reclaim a little personal space. You're practically required to try the signature drink, a margarita.
Lovers of vintage bar rooms will be in heaven at this veritable 1950s-era time capsule on Division Street: After shuttering in 1975, it was left undisturbed until 2015, when a local hospitality group dusted off the warm wooden interior and reopened the doors. Today there’s an emphasis on nautical quaffs like grog and navy strength gin. The Sunday and Monday oyster and martini happy hour is a favorite with locals.
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.
A favorite after-work watering hole with a substantial bar menu, Andy's Jazz Club has live music ranging from swing jazz to bebop.
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.
At Baton Show Lounge, boys will be girls. The lip-synching revues with female impersonators have catered to curious out-of-towners and bachelorette parties since 1969. Some of the regular performers, such as Chilli Pepper, have become Chicago cult figures. The more the audience tips, the better the show gets, so bring your bills.
North Side stalwart Beat Kitchen brings in the crowds because of its good sound system and solid rock, alternative-rock, country, and rockabilly acts. It also serves soups, salads, sandwiches, pizzas, and desserts.
This Logan Square cocktail go-to with an impressive catalog of vintage spirits focuses on elevating classic drink recipes by using unexpected ingredients. The Charlie Trotter's alums who opened Billy Sunday cheekily named the bar for the Prohibition-era temperance evangelist.
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.
In an upscale part of downtown, Blue Chicago has none of the trademark grit or edginess of the older South Side blues clubs. What is does offer is a good sound system, a packed calendar that regularly features female vocalists, and a cosmopolitan audience that's a tad more diverse than some of the baseball-capped crowds at Lincoln Park blues clubs.
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.
Once an metal factory and later a taxi cab repair shop, this 18,000-square-foot industrial conversion has an invitingly funky restaurant and bar up front. But the main draw is the midsize music room that accommodates 700 concertgoers—good for an up-and-coming underground act, or a higher-profile touring band looking for an intimate feel.
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.
Like its siblings in Miami, NYC, and elsewhere, Chicago's Broken Shaker specializes in highly creative cocktails, with a rotating menu that leans to the savory side. On one visit, we sampled a "Log Cabin Old Fashioned," with a hint of maple and garnished with a slice of toasted waffle; also look out for the Daiquiri of the Month. The bar itself is on the small side, but seating and service spill out into the Freehand hotel lobby.
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