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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.
Once a 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.
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 "Turn Up," with mezcal, Cynar, mango, coconut, and lemon. The bar itself is on the small side, but seating and service spill out into the Freehand hotel lobby.
This breezy, seasonal, casual bar and grill puts you so close to Lake Michigan that you might consider wearing a swimsuit. Perched atop the North Avenue Beach Boathouse, Castaways creates the perfect setup for lazy summertime sipping.
This ambitious bar and lounge, open till the early morning hours, offers a different environment on each of the four levels and high-quality cocktails throughout. Highlights include the fourth-floor Roof Garden, a year-round escapist experience under a fully retractable glass rooftop, and DISCO, on the third floor, which captures the energy, glamour, and sexiness of the 1970s in NYC, Paris, and Rome. DJs spin classics, deep cuts, and disco that evoke Studio 54 and Paradise Garage.
This longtime country-and-western themed outpost still hosts line dancing two nights a week (with free lessons!) plus karaoke and bingo nights, and there's also a variety of queer acts throughout the week including all-male revues and multiple drag performances.
The eye-catching Carbide and Carbon Building has its first rooftop bar. The Pendry Chicago Hotel, the skyscraper’s latest occupant, turned a former private-event space on the 24th floor into a chic indoor-outdoor lounge overlooking the Chicago River. The wine list emphasizes rosés (there are even several rosé cocktails), the kitchen offers sushi and small bites, and after dark, DJs spin French house.
Chef’s Special brings fun energy to Bucktown’s bar scene with brightly flavored cocktails in colorful shabby-chic digs. Don’t snooze on the menu of kitschy classic Chinese-American dishes; the kitchen is overseen by the team from Giant, the Logan Square favorite. Happy hour, held every evening from 5pm to 6 pm, means the place is packed within minutes of opening.
This compact dive bar—one of the few that caters to lesbians, though it draws gay men, too—has an after-hours license, meaning the party's only getting started at 2am when when most other bars are at last call. Karaoke nights at The Closet are particularly energetic.
A dark, wood-paneled room in the Drake Hotel, Coq d'Or has red-leather booths where Chicago legend Buddy Charles held court before retiring. Live music on weekends and cocktails served in blown-glass goblets draw hotel guests as well as neighborhood regulars.
The old-school taverns tucked at random along Bucktown's residential streets---many distinguished by a vintage Old Style beer sign---are a major contributor to the neighborhood's character, and this one (the latest iteration of a series of bars that have existed on this site since the 1950s) is a prime example. Come for the ice-cold beer, the easygoing dive vibe, and the jukebox tunes.
Diagonally across the street from Wrigley Field stands the Cubby Bear, a Chicago institution since 1953. It's the place where Cubs fans come to drown their sorrows in beer or lift one to celebrate. There are plenty of TVs for game watching, plus live music and a menu featuring burgers and other bar food.
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.
A rare dive bar amid Lincoln Park's tonier establishments, Delilah's is dark and a bit grungy. But the bar has a friendly, unpretentious vibe and a standout whiskey selection (more than 800 types are on offer). DJs spin punk, metal, and rockabilly.
When you combine an amazing whiskey list and tons of great craft beers with a dark, intimate space that plays great music like punk, rockabilly, alt-country and other outsider tunes, you get Delilah's. One of the coolest bars in Chicago for over three decades, Delilah's is a destination whether you want a rare pour of a hard-to-find bourbon, a game of pool, or just a cheap shot and a beer (because you can get one of each for just a few bucks every day).
Delicious lagers, smoked beers, and funky barrel-aged beers are specialties of this Eurocentric craft brewery. The rustic taproom offers snacks and easier-drinking shandies, and the brewery tours go deep into the interesting processes Dovetail uses to create their beers.
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.
Two of America’s favorite pastimes—drinking and playing classic arcade games—come together here. More is more is the governing M.O.: there are over three dozen arcade games to choose from, along with Skee-Ball, pinball machines, and around two-dozen beers on draft. There are also locations in Logan Square and the West Loop.
Mexican spirits like mezcal, sotol, and raicilla are the focus at petite Estereo, which has an unusual triangular shape due to its position on an angled corner lot. When the garage-style windows that surround the room are rolled up and the vintage Latin tunes are pumping, you’d be forgiven for thinking you’d been transported to a city much nearer to the equator.
Imported wood, stone, and glass are used to create Fadó's Irish look. The second floor—with a bar brought in from Dublin—feels more like the real thing than the first. Expect expertly drawn Guinness, a fine selection of whiskeys, a menu of traditional dishes, and live music on weekends.
Although it's a 30-minute schlep west of downtown Chicago, FitzGerald's draws crowds from all over the city and suburbs with its mix of folk, jazz, blues, zydeco, and rock. This early 1900s roadhouse has both great sound and sight lines. There's a menu of fantastic barbecue fare from Babygold, the adjoining restaurant. During the family-friendly Sunday brunch, it's paired with live acts that run the gamut from classic country to New Orleans funk.
Full of sports fans and former frat boys, Gamekeepers has more than 40 TVs, three projection screens, and complete satellite sports coverage. There's barely a game it doesn't get.
If you're in search of some footy on the telly, a proper pint of cider or stout, or pub grub like shepherd's pie or a full English fry-up breakfast, The Globe Pub should be atop your list. This North Center bar and grill is decked out wall-to-wall inside with soccer jerseys and team garb, while a patio allows for sunnier sipping in warmer weather.
Just up the street from Wrigley Field, Gman Tavern is a welcoming neighborhood tavern whose vibe is the opposite of the many rowdy sports bars nearby. The back room is outfitted with a small stage, a full bar, and a top-notch sound system for live music and comedy shows (it's also where a scene from The Color Of Money was filmed). In the front room, the well-stocked jukebox and well-curated beer list keep regulars and Cubs fans coming back.
This welcoming, female-owned tavern has been serving the city's craft beer scene since opening in 2011. The ever-rotating draft list focuses on local breweries from around Chicago like Spiteful Brewing and Half Acre, while also exposing patrons to more exotic beverages like the puckeringly sour Duchesse de Bourgogne from Belgium. A small array of wines and spirits supplement the drinks list, and patrons regularly pack the place for trivia nights and Euchre tournaments.
There aren't many reasons to make a special trip to the Bowmanville neighborhood, but Half Acre is certainly one of them. Head to their taproom to see where their legendary Daisy Cutter pale ale is produced, and while you're there, you can sip a pint in their beer garden or enjoy a plate of fish-and-chips or a katsu sandwich from their kitchen.
