Andy's Jazz Club
A favorite after-work watering hole with a substantial bar menu, Andy's Jazz Club has live music ranging from swing jazz to bebop.
Rush Street may have lost its former glory, but the bars along Division Street still attract rowdy singles. Reprieve from the bustling Division Street scene is only a few blocks south, in the Near North and River North neighborhoods. Hunker down in a low-key lounge or sip a hearty pint of Guinness at an authentic Irish pub. At the southern edge of River North, waterfront lounges popular with the after-work crowd line the Chicago Riverwalk.
A favorite after-work watering hole with a substantial bar menu, Andy's Jazz Club has live music ranging from swing jazz to bebop.
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.
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.
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.
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.
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.
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 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.
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.
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.
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.
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.
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.
Sound-Bar is a two-level labyrinth of nine bars, each with a unique design and color scheme (some even serve matching colored cocktails). Feel like dancing? Join the pulse of Chicago's best-dressed on the huge dance floor.
This late-night underground dance club has been in the River North area for more than 25 years. Featured are internationally renowned and up-and-coming local musicians and DJs.
Once you’ve found the alley entrance (hint: look for the red-roped line of people waiting outside), descend the glowing skull-lined stairs to reach this hip spot that’s an homage to the mid-century tiki craze. "Three Dots and a Dash" is an old-school, rum-based tiki cocktail that gets its name from the morse code for the letter "V" as in victory, as used in WWII. There are Pan-Pacific nibbles, like the shareable pu pu platter, to accompany the strong tropical cocktails adorned with flowers and served in tiki mugs.
This subterranean dance club has dropped the quasi-military underground bunker theme it once sported, but it still attracts celebs, international DJs, and the clientele that follows both.
Small and funky with zebra-striped lamps and other kitschy accoutrements, this lounge attracts an interesting crowd of dressed-up and dressed-down regulars who come to sing along with the pianist on duty.
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.
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.
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.
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.
The Motel Bar has all the comforts of a real, honest-to-goodness motel bar (TVs tuned to sports, classic cocktails, and a retro color scheme), but the atmosphere is amped-up with sexy, low-rise furniture and a "room service" menu of upscale bites.
Designer Nate Berkus assembled Rockit's hunter-lodge look: picture wood-plank-framed plasma TVs, antler chandeliers, and brown-leather booths. The crowd, much like the beer list, is diverse and tasteful, and there's a good mix of men and women despite the masculine vibe. Dress to impress.
The famous Chicago bar scene known as Rush Street has faded into the mists of time, although the street has found resurgent energy with the opening of a string of upscale restaurants and outdoor cafés.