Nightlife in Chicago (2024)

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 co*cktails, 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.

Bull & Bear amps up the testosterone, with a dual focus on sports—the bar's name references two Chicago sports teams—and the stock market. Reserve one of five booths with built-in beer taps (you pay by the ounce), or grab a seat at the bar and catch the game on one of several flat-screen TVs.

Bungalow by Middlebrow wears a lot of hats---brewery, 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. The owners also run an apprenticeship program that helps train at-risk youth for employment in the hospitality industry.

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 co*cktails 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.

A country-and-western dance spot, Charlie's lets you two-step nightly to achy-breaky tunes (club music takes over after midnight). It's mostly a boots-and-denim crowd on weekends.

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 co*cktails), the kitchen offers sushi and small bites, and after dark, DJ's spin French House.

Chef’s Special brings fun energy to Bucktown’s bar scene with brightly flavored co*cktails 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 Logan Square favorite Giant.

The springtime Chicago Improv Festival, the nation's largest festival for improvisers, has stages devoted to group, pair, and single improv; sketch comedy; and more.

The biggest dance club in Boystown is a stripped-down hall energized by flashing lights, booming sounds, and a partying crowd. Take a break in the up-front martini bar.

Everyone's welcome at Citizen Bar, a sleek space with exposed brick walls and traditional bar fare. But the real draw is the huge, multilevel outdoor area—it's one of the city's most coveted spots come summer.

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. Fine music and co*cktails served in blown-glass goblets draw hotel guests as well as neighborhood regulars.

Diagonally across the street from Wrigley Field stands the Cubby Bear, a Chicago institution since 1953. It is the place where Cub 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.

Davenport's, a sophisticated cabaret booking both local and touring acts, brings a grown-up presence to the Wicker Park club scene. The piano lounge is set up for casual listening, while the cabaret room is reserved for ticketed performances with a two-drink minimum.

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, ska, and rockabilly.

For vestiges of the old Rush Street, continue north to Division Street, between Clark and State. The watering holes here are crowded and noisy, and the clientele consists mostly of suburbanites and out-of-towners on the make. Among the better-known singles' bars are Butch McGuire's, the Lodge, and Original Mother's.

Double Door is a hotbed for music in Wicker Park. The large bar books up-and-coming local and national acts from rock to acid jazz. Unannounced Rolling Stones shows have been held here. Door No. 3, a lounge with a speakeasy theme, occupies the basem*nt.

This unmarked "secret" bar carries through with its speakeasy theme—the only sign you’re in the right place is the red light above the door. Inside, the lights are dim, the drinks (cash only) are cheap, and the whiskey choices are plentiful. DJs spin funk, house, and other genres; seek out the decked-out elevator room for the best seat in the house.

Elbo Room, a multilevel space in an elbow-shape corner building, has a basem*nt 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 24 beer taps. There's also a Logan Square location at 2363 North Milwaukee Avenue.

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 Fado'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 by fine dining vet John Manion, so do come hungry, and if you just can't bear trekking back to the city, consider booking into the so-called Sleepover Castle, a three-bedroom boho rental apartment above the bar.

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.

Up the street from Wrigley Field, Gman Tavern deftly manages to avoid being pigeonholed as a sports bar. The back room is outfitted with a small stage and top-notch sound system for live music and comedy shows; in the front room, the well-stocked jukebox and extensive beer list keep regulars and Cubs fans coming back.

Located in Ukrainian Village, this neighborhood institution is known for its cheap beer, Ping Pong tables, and, when the weather cooperates, its massive beer garden. There’s no kitchen, but Chicago’s own “tamale guy,” who sells authentic Mexican tamales out of a cooler, swings by nightly. Be sure to hit an ATM before you arrive because Happy Village is cash-only.

Rat Pack aficionados will appreciate the 1950s decor at this self-described "Swinger's mecca." Down a pint of beer and scan the typical (but tasty) bar menu as you listen to Frank Sinatra crooning on the well-stocked CD jukebox. The back room, in contrast, hosts karaoke, trivia and storytelling events on weeknights and '80s and '90s dance parties on the weekends.

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. Pricing begins at $175 for a table of four ($40 of which can be applied to your bill); semi-private and private party packages for bigger groups also available.