Chicago's Best Rooftop Bars

Chicago's restaurant clout has hit a high, and it's equaled only by the bars and lounges. A hub of secret tippling activity during the Prohibition era, Chicago now has a well-known and well-publicized cocktail culture. From the sports-obsessed Wrigleyville strip to the swanky, see-and-be-seen clubs in River North, there truly is a watering hole for everyone. For the spots that come out on top, just look up. Rooftop bars are taking over, and everyone wants to be above the cut (and the sidewalks). They're the perfect places to take in some sun and fun during the afternoons, or for a nightcap overlooking the sparkling cityscape. We've rounded up some of our favorite Chicago rooftop bars and lounges. Even if you're afraid of heights, the views, inventive menus and cool atmospheres will keep you grounded. 

Vertigo Sky Lounge

Stunning views, tempting small plates and signature cocktails, and cozy seating around a firepit make this 26th-floor indoor-outdoor penthouse lounge atop the Dana Hotel and Spa a tempting late-night destination.


On the 27th floor of theWit Hotel, this 7,000-square-foot rooftop lounge scores with gorgeous city views, live music and DJs, and a creative small plates menu. Thrill-seekers can request the glass-enclosed table for eight hanging over the city. Open M-F 4 pm-2 am; Sa 2 pm-3 am.

Streeterville Social

Something of an anomaly when it comes to rooftop lounges, Streeterville Social skips the bass thump of the club scene and goes for more of a country club feel.

Rock Bottom Restaurant Brewery

This lively River North neighborhood brewery offers a wide variety of brews handcrafted on site. The menu features traditional American fare and innovative recipes. Private event spaces accommodate up to 250 guests, cocktail style. L, D (daily).


Evoking turn-of-the-century Chicago glam, this River North hybrid dashes the glitz on multiple floors, starting with a vintage bar. In the Deco Room, find a 1920s supper club vibe for feasting on dishes such as Moroccan chicken pita and salmon with herbed spätzle. Come summer, escape to a Victorian-inspired rooftop garden.


Make your way to the 18th floor of the Raffaello Hotel for Hancock Building, Lake Michigan and Water Tower Place views. Quench your thirst with an impressive array of tincture-laced cocktails, by-the-glass vinos and bottle service, all the while absorbing the swank, speakeasy vibe.

Terrace at Trump

One of the city’s most primo patios, this 16th-floor oasis scores with postcard-worthy views of the Wrigley Building and Tribune Tower. Open daily 2:30 pm-12:30 am.

Virgin Hotels Chicago

The Virgin brand is now in Chicago with its first hotel. Designed from a 1920s bank in the heart of the city, with the restored original fixtures, this 250 room hotel—with 2 penthouses, 40 suites and 40 pet-friendly rooms—is making itself at home in the Windy City.


Though it has much in common with the neighborhood’s trendy Brazilian steakhouses—think deluxe salad bar and an assortment of all-you-can-eat meats brought by chefs to your table—this River North destination goes for a more varied menu, with dishes like citrus salmon and goat cheese-encrusted rack of lamb.


It's a rooftop terrace bar, but located on the third floor of the Renaissance Chicago Downtown Hotel the views are more intimate than sweeping. Views of the Chicago River and of Marina Towers right across the way.