C-View, on the 29th floor of MileNorth, feels like a secret hideaway.

C-View
As one of the city's few year-round rooftop bars offering panoramic views of downtown, C-View attracts tourists as well as residential crowds to its exotic outdoor patio and adjacent indoor bar. Less scene-y than other hotel rooftop spots, this 29th-floor lounge of the MileNorth hotel still feels like a secret hideaway. 166 E. Superior St., 312-523-0923

Drumbar
With an opening this month at the Raffaello Hotel, this spot brings a taste of Miami to the Gold Coast. Pass through dramatic arched doors to hit the two rooftop oases—one features lounge seating and small bites; the other sports cooking grills and a more casual ambiance. Of course, both boast stellar classic cocktails and lake views. 201 E. Delaware Pl., 312-943-5000

Epic Sky
Arrive early if you expect to nab one of the few cabanas for a couple of rounds of after-work cocktails (cabanas are available on a first-come, first-served basis, with no bottle-service requirement). The crowd is sharp, typically single, and ready to mingle. 112 W. Hubbard St., 312-222-4940

Lakeview Baseball Club
Getting tickets to this venue to watch the Cubs play is as challenging as scoring first-row seats behind the plate. But once you're in, it's all-inclusive: an open bar and a buffet of burgers, brats, and hot dogs for the duration of the game. Jaw-dropping sight lines, open seating, and easy access to the bathrooms are also nice perks. 3633 N. Sheffield Ave., 773-935-1880

NoMI Garden
You know it's summer when NoMI Kitchen's patio officially opens for business. The restaurant's 2011 renovation gave it a more approachable vibe, along with an impressive new craft cocktail program and shareable bites. 800 N. Michigan Ave., 312-239-4030

The Plymouth
Someplace needed to fill the void now that Trader Vic's is no longer a kitschy mai tai joint. This Loop lounge looks and feels like a swingin' sixties watering hole, complete with photos of Hollywood's Rat Pack, as well as legendary Chicago personalities like Mike Ditka, Oprah, and John Cusack on the walls. 327 S. Plymouth Ct., 312-362-1212

SushiSamba Rio
The vibrant setting and tropical beats add warmth to this rooftop spot no matter what the weather. The bar is completely covered, making it the perfect spot to sip mojitos and caipirinhas whether it's balmy or brisk. Either way, it's a see-and-be-seen kind of bar. 504 N. Wells St., 312-595-2300

The Terrace at The Peninsula Chicago
Adjacent to the splendid Shanghai Terrace Chinese restaurant, The Terrace is one of the more luxurious rooftops in the city. Here, you'll sip Champagne or cognac on luxurious, plush, custom-designed outdoor furniture that you'll instantly covet for your own home. 108 E. Superior St., 312-573-6744

The Terrace at Trump
Those without access to a summer rooftop with views of Navy Pier's twice-weekly fireworks can camp out here for the perfect sight lines. Seating is hard to come by, so reservations are highly recommended. Premium cocktails—like the $81 Iva Sefulu, made with Gran Patrón Platinum tequila, Grand Marnier 150, and Mediterranean sea salt—and seasonal punch bowls make the experience extra special. 401 N. Wabash Ave., 312-588-8000

Vertigo Sky Lounge
Clubby crowds in designer jeans and dresses frequent the Dana Hotel and Spa's showy cocktail bar with a Vegas attitude. DJs spin high-energy music and there's plenty of eye candy to go around. 2 W. Erie St., 312-202-6060

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