37 Best Bars in Chicago, Illinois

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.

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.

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.

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 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. 

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 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.

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).

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.

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.

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. 

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.

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.

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. 

Pops got its start more than 40 years ago and it's Chicago's only champagne bar. These days there's a focus on small-grower producers. The basement is home to Watershed, a cozy spot with limestone walls focused on Great Lakes regional craft beers and spirits.

Chicago hipsters and indie rockers have made Rainbo Club their unofficial meeting place. Apart from the working photo booth wedged into a corner, the stripped-down hangout is pretty barren, but drinks are dirt cheap and the crowd is loyal.

It’s hard to imagine a bar feeling homier than Rogers Park Social. The community-oriented spot has an impressive menu of craft beers plus fresh cocktails that pack deep layers of flavor into every glass.