Nightlife in Chicago

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.

Rittergut Wine Bar Restaurant & Social Club crafts the perfect wine, seafood, and steak experience, with seating that overlooks the Chicago River. Wine by the glass and bottle from the vineyards of Spain, Austria, France, and Italy complements charcuterie and imported cheese plates stocked with wild boar salami or herb-laden garrotxa goat cheese, much like the contents of an enophile's personal bomb shelter. The tasting bar and private wine rooms set the stage for uninterrupted swilling, while dining rooms bathed in amber light host feasts of lamb burgers seasoned with Moroccan spices. Arched ceilings draw the eye downward to exposed brick walls and hardwood floors indoors, and a riverside patio with dark wicker booths and wooden tables perch patrons over ebbing crests and bottled messages that implore you to try the salmon.

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.

A towering, 35-pound pile of Angus beef, American cheese, and bacon awaits those who accept the Da Big Hurt Challenge at Shoeless Joes Ale House & Grille, the 22-year-old sports bar that has won over Chicago diners and Channel 2 News alike. Diners who tackle the challenge are rewarded with a T-shirt and are automatically entered to win the next presidential election. Guests with smaller appetites can enjoy more reasonably sized selections from the sports bar's menu of 14 gourmet burgers, steak, ribs, and pizza. Meals pair with pours from an impressive wine list or the roster of more than 20 craft beers on tap. The restaurant's 36 flat-screen televisions beam sports into the pub throughout the week while guests shoot pool, and singers belt out karaoke tunes on Saturdays.

Only a true icon can name their venue Legends and get away with it. Luckily, famed blues artist Buddy Guy fits the bill. Known as ?the crowned king of Chicago?s electric blues scene,? Buddy has more than 50 years in music notched into his guitar strap, as well as six Grammy Awards and a coveted spot in the Rock & Roll Hall of Fame. Inside his beloved blues club, Guy can be seen on stage every January during sold out shows, easing into the playful stomp of Muddy Waters? ?Hoochie Coochie Man? and his soulful, woozy solo in ?Stone Crazy.? The performance space holds fans? intrigue with other performances throughout the year and has hosted such renowned musicians as John Mayer, ZZ Top, David Bowie, and Eric Clapton. Seven nights per week, live blues music drifts through the air while guests dine on southern Cajun soul food, from blackened bourbon shrimp to cat fish po? boys and chicken and sausage jambalaya. Music fans can sneak away from their meals to fawn over blues memorabilia such as original artwork, Grammys awards, and guitars signed by B.B. King, Carols Santana, and the late Stevie Ray Vaughan.

Lively jazz tunes bounce off the brick walls, exposed rafters, and blue-tinged décor of Close Up 2 Jazz's South Loop location. Bartenders shake cocktail mixers in syncopation with smooth jazz that flows from a floor-level stage. Up-and-coming artists mix R & B and classical jazz in the loft-style lounge, whose music and ambiance have attracted numerous mentions in the press. Just steps from the LaSalle/Van Buren Brown Line stop, the chic club leaves its doors open from 4 p.m. to 2 a.m. on weekdays and 9 p.m. to 3 a.m. on Saturdays to catch the postwork crowd and recently retired "L" train cars.