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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.
It's probably just our imaginations, but somehow the sunlight that streams over the vintage tiles and velvety banquettes in this easy-going Humboldt Park cocktail bar seems to glow. An equally dreamy side patio has a second bar and a brick fireplace flanked by lots of low seating for basking in the firelight once the sun sets. Dogs are very welcome here.
Rat Pack wannabes or anyone looking to relive the swing-dance dream of the 90s will appreciate the mid-century decor at this modern-retro lounge. Order a martini and scan the straightforward bar menu as you vibe to crooners like Frank and Dino on the digital juke box. The back room hosts comedy open mics, karaoke, trivia, and storytelling events on weeknights and 80s and 90s dance parties on the weekends.
Home to the haziest IPAs and biggest barrel-aged stouts, Hop Butcher is the place to be for a look at the cutting edge of American craft beer. Stop by the taproom for a flight or a pint or hit the retail store for some merch or a four-pack of cans to go.
Among the performers at this fun spot are dualing pianists who encourage the crowd to belt out popular songs. Walk-ins are welcome, but weekend table reservations can be purchased in advance. Table reservations range from $60 to $275 for a table of four ($40 of which can be applied to your bill); semiprivate and private party packages for bigger groups also available.
Billing itself as a "Continental tavern," this two-story River North hot spot pays homage to Ernest Hemingway's travels with classic cocktails and eclectic, globetrotting decor—think Moroccan tiled walls, vintage books, dramatic oil paintings, brass light fixtures, and tables made from reclaimed wood. Small plates are designed with communal dining in mind, though you may want to keep your perfectly balanced Sazerac all to yourself.
One of the best-known queer night clubs in Chicago, Hydrate combines a relaxed front lounge with a late-night, high-energy dance floor in the back. Weekly events include DJs, drag shows, and viewing parties for RuPaul's Drag Race when the show is airing. Sundays see the post-brunch crowd stopping in for drinks and then dancing well into the night.
Formerly called ImprovOlympic, I.O. is the city's home for long-form improvisation. The signature piece is "The Harold," in which a team of improvisers explores a single audience suggestion throughout a series of stories and characters until they all eventually weave back together to fit with the original audience idea. There's no drink or age minimum. Seating is first-come, first-served, so be sure to arrive early, especially for weekend shows.
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.
Popular Kincade's packs 'em in on two levels with a 10-foot-wide video monitor, several plasma screens, and a bar menu that invites patrons to linger for a game—or three. An outdoor beer garden, pool tables, and French doors that prop open on warm summer days are added bonuses.
In 1968, Kingston Mines went down in Chicago history as the first blues club to open on the North Side, and it's hosted luminaries like Koko Taylor and Junior Wells. Though it's since moved to bigger digs with not one, but two stages, it still offers the same traditional sounds and late-night hours as the original club. Have something you need to get off your chest? Work it out at the Sunday evening open blues jam.
This handsome spot in the Hilton Chicago is an authentic Emerald Isle pub with all things Irish, including live music Thursday through Sunday, beer, food, and bar staff.
Enjoy late-night music, potent martinis, and Gothy vibes? Late Bar, located along a somewhat lonely stretch of Belmont Avenue, is the place for you. The best time to come is Saturday night, when the club is bumping with New Wave classics until 5 am.
This outpost of the Laugh Factory is part of the chain of comedy clubs that has locations in Hollywood and Las Vegas, among others. Shows like Chicago's Best Standup, The Nasty Show, and Latin XL take place throughout the week while national headliners also appear regularly.
Done up in pretty Prussian blue with warm walnut accents, this wine bar/bottle shop channels calm vibes—and if you're still feeling keyed up, a pour or two from the Eurocentric wine list should do the job. Standard wine bar fare like cheese and charcuterie plus a few Spanish-inspired pintxos make up the small food menu.
The owners of Lincoln Hall transformed a former movie theater into an intimate concert space with great sight lines, an excellent sound system, and a wraparound balcony with seating. The booking is always on point, so it's worth taking a chance on a lesser-known band. A separate bar up front pours preshow pints from local breweries.
This comedy showcase started in the back room of a Lincoln Square diner, where for years young comics like Hannibal Buress, Cameron Esposito, and Kumail Nanjiani honed their stand-up. The Lodge now has its own venue in Bucktown, where you can find the next generation of comedians working the room most nights of the week.
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.
This inviting bar is the perfect spot to wait out the long lines at nearby restaurants Au Cheval or Girl & the Goat. The tiny but mighty menu of bar snacks (homemade corn dogs, grilled cheese, spicy fries) will tide you over nicely; solid takes on classic cocktails and a healthy rotating draft list make it a welcome addition to the restaurant-heavy ’hood.
Come summer, Ludlow gets top marks for its spacious back patio, and when the weather goes south, it's hard to fathom a cozier spot than one of the high-backed stools that flank the handsome vintage bar. Whatever the season, the drinks here are stiff, and the smash burgers hit the spot. Check the website for the monthly roster of quirky events, like musical bingo nights and tarot readings.
The Map Room might help you find your way around Chicago, if not the world. Guidebooks decorate the walls of this self-described "travelers' tavern," and the craft beers represent much of the globe. This is a favorite gathering spot for soccer fans, so expect it to be roaring during World Cup season.
Tucked onto a side street slightly removed from Andersonville's main stretch of Clark Street, minuscule Marty’s has been serving up some of the tastiest cocktails in the neighborhood for two decades. Roughly the size of a one-bedroom apartment, the bar can get very crowded, so come early in the night (or just escape to the outdoor patio).
Martyrs' brings mostly local rock bands (and the occasional major-label act) to North Center, a small neighborhood sandwiched between Lincoln Square and Roscoe Village. Music fans can see the stage from just about any corner of the bar, while the more rhythmically inclined gyrate in the large standing-room area. A mural opposite the stage memorializes late rock greats.
Nearly everyone who passes through Chicago plays at Metro at some point, from the best local bands to international superstars looking for an intimate club show experience (including bands like Metallica and Foo Fighters). It's among the best places in town to see live music, whether you're packed in on the main floor or above the fray in the balcony. In the basement is Smart Bar, a late-night dance club that starts hopping after midnight.
Local beer geeks flock to this minimalist taproom, stationed along a rather unassuming stretch of repurposed industrial buildings, to sample the latest pours from Off Color Brewing. Traditional European styles with a twist (Berliner weiss brewed with Chardonnay grapes, for instance) are the order of the day here.
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.
Hidden behind the the kitchen door of Moon Palace Express is Chinatown’s first cocktail bar. Neon lights illuminate Nine Bar’s sleek, dark space, and Asian-inspired cocktails with ingredients like Sichuan peppercorns and rice vodka feature on the menu. Don’t overlook bites like mapo fries, wings, and the chicken sandwich on the small food menu.
This unassuming joint claims the mantle of Wrigleyville's oldest bar, operating continuously since 1951. Whether it's thronged with Cubs fans on game days or by its loyal regulars in midwinter, the Nisei exudes a welcoming, divey vibe. If you want to sample Malört, Chicago's favorite unbelievably bitter liqueur best described as an acquired taste, no bar will be happier to introduce it to you.
Named for its location at the north edge of Boystown, this decades-old gay-friendly sports bar is a favorite spot for watching the game, shooting some pool, throwing some darts, or just having a cheap beer with friends.
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.
Since the 1960s, The Original Mother's has been a local favorite for cutting-edge music and dance-'til-you-drop partying. The subterranean destination was immortalized by Demi Moore, Jim Belushi, and Rob Lowe in the '80s rom-com About Last Night.
