The third-largest city in America, Chicago offers an eclectic blend of sybaritic excitement, especially come darkness, when the stunning skyline shimmers over the shore of Lake Michigan. Its 77 distinct neighborhoods teem with buzz-worthy restaurants, bars, theaters and clubs, plus enough cafés to keep the midnight fuel burning. Add super-friendly locals, and it’s no wonder nearly 40 million people visit Chicago annually.

When the work day cools off, Chicago’s cocktail scene heats up — from neighborhood dives like Guthrie’s Tavern with board games and local beers to chichi lounges like Chef Grant Achatz’s Aviary in the Meatpacking District, where mixologists create fanciful, liquid works of art. In between, you’ll find hip watering holes like The Violet Hour; Billy Sunday, featuring drinks with exotic ingredients like maidenhair fern syrup and lusty bar bites (pig’s ears and jarred chicken livers); and The Drawing Room, a subterranean space in the ritzy Gold Coast with excellent cocktails, sophisticated mocktails (try the lemon and bitters soda) and locavore small plates. The Back Room, next door, has offered live music (jazz, R&B, swing and more) since 1968, while The Whistler, a West Side art gallery, record label and bar, features live music and a DJ seven nights a week, along with exotic libations like the Modern Medicine (rum, Drambuie, lemon, lime and banana bitters).

For eats, Chicago is your oyster, although as the largest meatpacking center in the country until the 1920s, it has long been known for meat. A stellar spot downtown is The Publican, an “homage to beer, pork and oysters.” Nearby lies Girl and the Goat, known for earthy fare like squash wontons, grilled octopus with beans and goat loin with pickled grapes. Locals also favor Siena Tavern’s scrumptious Italian fare like farro risotto with wild boar. For cutting-edge dining, snag a seat at Fat Rice for Asian-Portuguese comfort food laced with linguica, Port and salt cod. Then there’s the Chicago hot dog — a pure-beef frank on a poppyseed bun topped with tomatoes, pickled peppers and a dill pickle wedge — best at Hot Doug’s, also famous for duck fat fries.

For a little action after all that eating, Millennium Park has free ice skating (and rental skates) until mid-March, weather permitting. The Underground on the Near North Side draws celebrities for VIP bottle service and DJ dancing in a posh subterranean lounge. The heart of Chicago’s LGBT community is Boystown, home of the Kit Kat Lounge & Supper Club, with nightly shows performed tableside. @tmosphere in the Swedish Andersonville neighborhood is a popular “upscale dive” known for its male go-go dancers.

One of the city’s leading theater companies is Steppenwolf, specializing in ensemble productions. Nearby is The Second City improvisational comedy theater, which launched the careers of John Belushi, Tina Fey and Steve Carrell. For jazz, head downtown to Jazz Showcase, founded in 1947 and featuring local and international talent seven nights a week.