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Chicago rooftop roundup

Take your group out for dinner or cocktails on a Chicago rooftop that offers the added bonus of a spectacular view. We’ve got six great ideas for rooftops on the lakefront and around the city to get your planning started.


Cindys interior

Inspired by a Great Lakes beach house with its glowing string lights and picnic table seating, Cindy’s is the breathtaking rooftop restaurant perched atop the Chicago Athletic Association Hotel. The vaulted glass-and-steel restaurant features jaw-dropping views of Millennium Park and Lake Michigan. Choose dishes from Cindy’s menu of refined American fare, including delectable seafood options. And be sure to order a round of unique craft cocktails, including the Jillian, made with spiced clementine shrub.

VU Rooftop

Rooftop lounge

Located 22 stories above McCormick Place is VURooftop, the South Loop’s first year-round rooftop restaurant and bar. The swanky penthouse space features outdoor terraces with fire pits, multiple bars, and epic city views. Groups can mingle in several different spaces, including the Karaoke Room, Club Lounge, and Solarium. Try a small plate, like the grilled shrimp with jerk glaze, or the pork belly bao. The pineapple margarita makes for a great refresher on a warm evening.

Roof on theWit

Roof on the Wit

ROOF on theWit, the lively rooftop lounge on the 27th floor of theWit hotel, keeps the party going all year-round, thanks to its retractable roof. With its modern design, glittering city views, and nightclub vibe courtesy of live DJs, it’s no wonder Travel + Leisure named it one of the top three rooftop bars in the world. Cozy up on a couch by the fireplace and indulge in bites like the artisan roasted mushroom pizza, paired with a throwback cocktail such as the Bee’s Knees (gin, honey syrup, and lemon).


Aba Rooftop Patio
Photo by Jeff Marini

Located atop a historic building in the hot Fulton Market district, Aba features a lush, plant-filled terrace with downtown views and fire pits for cool evenings. Chef CJ Jacobson’s menu was inspired by summer in the Mediterranean, and features a variety of hummus (try the artichoke version), kebabs, and entrees like the slow-braised leg of lamb wrapped in eggplant. The bar program showcases Mediterranean wines, including vintages from Lebanon’s esteemed Chateau Musar.

Gibsons Italia

Gibsons Italia

Gibsons Italia is a stunning, three-level Italian steakhouse that boasts sweeping views of the Chicago River. The main dining room is on the second floor, while the third floor features a lounge with a dramatic retractable roof that allows for year-round cocktails and picturesque water views that change with the season. Must-orders include the lobster cocktail and USDA-certified Gibsons Prime Angus filet mignon. Select a glass from the top-notch wine list or enjoy a classic Manhattan.

Offshore Rooftop & Bar

Offshore at Navy Pier
Photo by Heidi Harris

As the world’s largest rooftop venue, all-seasons Offshore Rooftop & Bar at Navy Pier has plenty to offer. The glass-enclosed, 36,000-square-foot venue offers stunning views of Chicago and Lake Michigan, along with a chic bar and restaurant, terraces with cozy fire pits, and an entertainment and gaming area. Offshore also provides a front-row seat to Navy Pier’s summertime fireworks shows. Finger foods such as sushi and the Nashville-style hot chicken sandwich pair well with easy-drinking cocktails like the Whiskey Tango Foxtrot (whiskey, mango, ginger, and lemon).


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