View from Above: 5 Rooftop Dining Spots You Can’t Miss


Fig & Olive – 104 E Oak Street

This beautifully-chic restaurant brings nature to you, with a huge tree positioned right in the middle of the bar. 

Enjoy light Mediterranean cuisine and perfectly crafted cocktails from one of the only rooftops in the Gold Coast area. It’s a truly unique Chicago experience full of foliage and considered a “hidden gem” among neighborhood locals — one that may not stay hidden for long.

Offshore – 1000 East Grand Avenue 

This is the nation’s largest rooftop bar located on the third floor of Navy Pier’s festival hall. The advantage of being out on a pier? Views you won’t find anywhere else. 

Enjoy classic cocktails with a twist and order from a diverse menu. They focus on seasonal, modern american cuisine with global influences served as small, shareable plates. 

Homestead on the Roof – 1924 West Chicago Ave

Most restaurants claim to be “organic” or “farm-to-table” but fail to detail where their food actually comes from. At Homestead on the Roof, they literally bring the farm to you. 

With a beautiful 1,000 square foot patio in the Ukrainian Village, this restaurant combines rustic American charm with innovative flair. Their organic gardens are situated throughout the dining room, allowing you to not only taste but see the ingredients they use. Consider it the perfect place to enjoy an early happy hour or relax with your friends on a Sunday. 

LondonHouse – 85 East Wacker Drive

LondonHouse sits high above the Chicago River — and just as the water flows, so do the drinks. Enjoy a cocktail or a glass of wine while you take in one-of-a-kind views at one of the city’s tallest rooftop restaurants. 

If you work up an appetite, try their crispy-skinned roasted duck or something a little more classic like their cheeseburger. Whatever you indulge in, one thing’s for sure — sitting 22 stories above some of the most picturesque sites in the city at this swanky rooftop lounge will have you feeling like royalty.

Cindy’s – 12 S. Michigan Avenue

The crown jewel of the Chicago Athletic Association Hotel, Cindy’s Rooftop is a restaurant and open-air terrace offering panoramic views of Millennium Park, sparkling Lake Michigan, the Art Institute of Chicago, and beyond. 

Executive Chef Christian Ragano and his team dish out seasonal, family-style comfort food, bio-dynamic wines and award-winning cocktails with large format apothecaries. Anything you order is sure to be fresh, locally-sourced, and in tune with the vibes of this Great Lakes beach house.

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