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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 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 legendary local acts like Wilco and Andrew Bird have been known to use the crowd here as a sounding board for new material. Late-night DJ sets, stand-up, and even the odd square dance round out the entertainment offerings.
A favorite after-work watering hole with a substantial bar menu, Andy's Jazz Club has live music ranging from swing jazz to bebop.
This is home base for Annoyance Productions, an irreverent group best known for hits like Skinprov and Hitch*Cocktails. Two theaters host multiple shows seven days a week, and drinks and snacks are available for enjoyment during the performances. The Annoyance is mostly focused on improv and sketch comedy, but there are also burlesque performances, open-mic nights, and more.
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.
Bungalow by Middlebrow wears a lot of hats---brewery, natural winemaker, sourdough bread bakery, pizzaiolo, all-day neighborhood third place---and looks darned good in all of them. There’s a relaxed, come-one-come-all feeling to the dining room and patio here; indie folk types play mellow sets while friends sip wild ales and families linger over pizza. Fun one-off events, like block parties and collaborative pop-up dinners, are frequent; check in with the house Instagram account ( instagram.com/middle_brow) to find out what's upcoming.
For a truly unique evening, try and find this cocktail bar hidden behind a storefront along Andersonville's Clark Street. Once inside, you'll find a bar where magicians perform up-close sleight of hand while patrons sip delicious cocktails. That's just the prelude to the main theater where feats of illusion and trickery are performed nightly.
This place 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.
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 legendary 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 (appearing nightly; cover charge required; cash only) is both excellent and contemporary, as are the monthly poetry slams.
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.
In West Town near Wicker Park, the Matchbox isn't much bigger than a you-know-what, but the hodgepodge of regulars doesn't seem to mind. In fact, many claim it's the dark, cramped quarters (we're talking three 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.
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 and a mural of bar denizens painted in the 70s, 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."
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.
On a given night at Rosa's Lounge, you'll find Tony, the owner, working the crowd. He moved here from Italy out of a pure love for the blues, and what makes his club special is a gritty authenticity that some of the sleeker city center blues establishments lack. 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. Take a rideshare after the show, as this corner of the neighborhood can be a bit rough around the edges at night.
The epicenter of comedy since 1959, The Second City has launched the careers of countless comedy legends, including 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 classic Andersonville bar telegraphs the neighborhood’s Swedish roots from the moment you walk under the bar's sign: a blue-and-yellow neon herring holding a cocktail glass. Don't miss the chance to sample their signature drink, glögg—mulled Swedish wine, served hot in a mug in winter and in frozen slushie form in summer. The Viking/Midwestern-chic decor is eclectic and divey, but in a very good way. (Ask about the story behind why someone was "cut out" of the decades-old mural on the wall.)
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.
Chef Grant Achatz applies his cutting-edge culinary style to cocktails at this West Loop bar, adjacent to his high-concept restaurant Next. Your newfangled old-fashioned might arrive injected into an egg of ice, or your drink's flavor might change subtly as its flavored ice melts. Inventive bar bites are on offer as well.
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 have become Chicago cult figures. The more the audience tips, the better the show gets, so bring your bills.
This North Side bar and music club brings in the crowds thanks to a good sound system and a great space for solid rock, alternative-rock, country, and rockabilly acts plus live local comedy during the week. On the Kitchen side, guests can order up salads, sandwiches, burgers, pizzas, and desserts. The well-earned popularity of the Belmont location spawned spots downtown on the Riverwalk and a Cantina location at Navy Pier.
You know a taproom takes beer seriously when they specify exactly what temperature their drafts are served at. That's the Beer Temple, an inviting space with around 20 ever-changing handles and lots of seating for the requisite beard-and-flannel types. Do pay a visit to the fantastic bottle shop, which precedes the taproom by several years. It specializes in super-limited-release local drops and brews from Belgium and France, and the staff's knowledge of obscure brewers and beer styles is mind-boggling.
Tucked into a residential spot of North Center between two rail lines is this friendly neighborhood craft brewery. Begyle's beers are often more approachable than other breweries, with blonde ales, pale ales, and kölsches taking center stage alongside IPAs and stouts.
The bartenders at this swanky but unfussy cocktail bar on the ground floor of the hip ACME Hotel specialize in improvisation—name a spirit, flavor profile, and type of glassware from the "Dealer's Choice" menu and they'll craft a drink for you on the spot.
This long-time uptown gay bar and artsy neighborhood restaurant offers a relaxed getaway from Northalsted during the day, and at night can get just as loud and boisterous as any bar in Boystown. Big Chicks has built a friendly, welcoming community around this little cocktail bar over the last few decades where a dance party could happen at any minute. In the morning, order some Bloody Marys alongside a hearty brunch.
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.
In an upscale part of downtown, Blue Chicago has none of the trademark grit or edginess of the older South Side blues clubs. What it 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.
