Best Rooftop Bars / Restaurants in Chicago

Looking for Chicago's best rooftop bar and restaurant? Look no further! The Windy City has a sky-high destination for everyone, from Downtown Chicago to The Loop and River North. Not only is it home to the world's largest rooftop bar and some fantastic Chicago rooftop pools, but it's also alive with colorful and stylish rooftop lounges with spectacular views of the Chicago skyline and Lake Michigan. While summer is the busiest and most popular season, many Chicago rooftop bars and restaurants are open all year.

Cindy's Rooftop

Location: 12 S Michigan Ave, Chicago, IL 60603

Contact No.: (312) 792-3502

A Rooftop restaurant and open-air patio with views of Millennium Park and the surrounding area. In between, stop by the rooftop bar for some snacks and expertly created drinks, local brews, or something from the impressive selection of wines.

Raised Bar

Location: 1 W Wacker Dr, Chicago, IL 60601

Contact No.: (312) 795-3444

An urban rooftop bar with a laid-back luxury vibe and spectacular views of Chicago. Locals and visitors alike may enjoy the outdoor/indoor bar, private outdoor areas, and a trendy open-roof terrace at Raised. The terrace offers to bar seating along the perimeter, which is ideal for people watching, as well as some very comfortable lounge sofas and fire pits.


Location: 122 W Monroe St, Chicago, IL 60603

Contact No.: (312) 750-9007

Even in the dead of winter, the Kimpton Gray Hotel's gorgeous rooftop bar feels like a tropical paradise. Drinks like the In the Morning, I'll Be Better, an addictive blend of plantain-infused Scotch, black walnut bitters, tiki bitters, and smoke, showcase South American flavors. Pair it with a plate of empanadas packed with flank beef, red pepper, and olives and served with chimichurri sauce, which is a fan favorite.

Reggies Rooftop Deck

Location: 2105 S State St, Chicago, IL 60616

Contact No.: (312) 949-0120

Reggies is most known for hosting rock concerts and providing shuttle service to White Sox games, but it also has a rooftop bar with tables and umbrellas. Take a seat, take in the views of State Street, and order from the standard menu of wings, burgers, quesadillas, and other pub fares while sipping a cold beverage in the sun.


Location: 118 W Grand Ave, Chicago, IL 60654

Contact No.: (312) 222-9700

Feast your eyes with its broad selection of a la carte menu and do-it-yourself kits for your Anticucho Skewers and Cebiche bowls. Next to its year-round rooftop terrace is a private dining room for any gatherings and occasions. Choose from a variety of personalized meal and beverage options, as well as bar packages featuring its Signature House Cocktails.

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