Nightlife in Chicago

As Tommy, one of Howl at the Moon’s piano players, explains on the club’s website, “Every night…we try and throw a party, regardless of whether it’s a Tuesday night or a Saturday night.” The bar’s trademark dueling pianos serve as the epicenter of these nightly celebrations; patrons submit their favorite songs on slips of paper for the pianists and backing musicians to recreate. If the website’s playlist is any indication, the bands can handle popular songs from all genres and eras, from Bon Jovi’s “Livin’ on a Prayer” to Kanye West’s “All of the Lights.” The performances are spirited: colorful lights splash upon a stage where servers, guests, and chairs that have somehow developed mobility all dance along to the music.

Fueling the celebration is the bar’s indulgent selection of drinks. Servers stand over patrons to plunge jello injectors into their mouths, and revelers grab colorful straws to help drain 86-ounce booze buckets filled with sangria or other fruity libations. Pomegranate liqueur and honey-infused whiskey sweeten specialty cocktails, and local beers add depth to coolers stocked with Stella Artois and Dos Equis.

Chicago Limo Net ushers its office-, nightlife-, and airport-bound clientele about the Chicago area in a fleet of luxurious, custom buses and limousines. Twenty-four-passenger party buses bedecked in low-level lighting, leather couches, dancing poles, and mirror-laden roofs bestow a nightclub-like feel minus the acute stares of gargantuan doormen. Smaller 6- and 10-passenger limousines present many of the same creature comforts in a more aerodynamic package for airport or around-town trips. Each party conveyance is piloted by a professional chauffeur with extensive knowledge of downtown Chicago, who will gladly take the fastest or most scenic route and can offer unique insights into the city, such as how to differentiate between the Willis Tower and the pier's ferris wheel.

While plantains make handy banana doppelgangers and semi-decent boomerangs, the sweet and starchy treats shine alongside island spices, savory meats, and sea-meats. Different in flavor and approach from other Latin cuisines, the Rumba Room's slow-baked sweet and spicy array of Cuban dishes is available for lunch (Monday–Friday) and dinner (usually Thursday–Saturday). If you're new to Cuban eats, try arroz con pollo ($8), a traditional, hearty dish of seasoned chicken with Puerto Rican–style rice, black beans, and sweet plantains or ropa vieja, a succulent seasoned and marinated beef slow-cooked until it falls apart. Spelunkers weary of Alabama cave shrimp can taste the real thing with Veracruz shrimp ($10) in garlic salsa, served with Puerto Rican–style rice, black beans, and tortillas. Specialty drinks like the Cuban mojito ($7) or rum runner ($7) present potable solutions to such dilemmas as lack of rum and taste for mint. If you use today's Groupon for lunch, you'll get a free order of light and sweet coquito rice pudding.

Situated in the center of the thriving Wicker Park neighborhood, 6 Corners Sports Bar quenches revelers' thirst for cold beer, live sports, and tasty pub fare every night. A 10-foot cinema screen and a chorus of 16 high-definition televisions blare athletic action year-round, from basketball playoffs to behind-the-scenes fisticuffs at the national spelling bee. The menu of hot wings, sliders, and wraps fuels diners for further pub crawling, and 23 bottled and on-tap beers wash down grub.

Michael Dorf stood with his brother Josh, smiling over the barrel filled with wine from grapes they'd just crushed, fermented, and pressed. He claims that despite tastings and classes, he'd never begun to understand wine until this moment. As his understanding grew, he laid the foundations for City Winery: a full winery facility, restaurant, and concert venue inside urban Chicago. He now watches over more than 400 international wines and 20 house wines. Inside the winery, these wines—made from nine US and international varietals—age inside stainless steel tanks and American and French oak barrels. Here, staffers lead winemaking classes, letting visitors join the crushing and fermenting process, and showing them how make private barrels and fill custom juice boxes or bottles pasted with labels of their own design.

These monolithic tanks and barrels can be seen through floor-to-ceiling windows from most of the restaurant's rooms, where servers ferry Executive Chef Andres Barrera's dishes, each a blend of Italian, French, Spanish, and Middle-Eastern flavors. The culinary team crafts small and large plates of artisanal cheeses, seafood, and flatbreads—which they make using the winery's own wine lees as yeast. In the restaurant and Barrel Room tasting bar, staffers pour housemade wines piped fresh from the cellar through 14 taps, while visitors bask in the glow from hard wood and floor to ceiling windows. Patrons dine on a ground floor lit by soft blue lights and hanging lamps fashioned from old wine bottles, as well as a mezzanine level looking out on the city skyline. Private dining rooms gather guests around long communal tables, stretched between exposed brick walls. In the show venue, comedians, live musicians, and slapstick-prone stage crew members entertain audiences under the glow of tabletop candles.

Island Sports Bar & Grill maintains the balance between good food and good fun, serving up hearty bar food to complement a full schedule of social events. The kitchen crew grills beef, turkey, and veggie burgers to order, and tops Vienna hot dogs with all the Chicago fixings. Meanwhile, customers strut their stuff during Monday-night line dancing and karaoke, or slap their knees in jubilant joy or subtle spasm during the Friday-night comedy hour. The middle of the week brings a host of events as well, from step and salsa dancing to live bands.