Chicago's Best Rooftops for Summer Fun

Updated November 23, 2018

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Raising the Bar

Having a cold beverage on a rooftop bar is a summer rite of passage in Chicago. You’ve likely caught a Cubs game or concert at one of the Wrigley rooftops and sipped your fair share of rooftop bevvs. This is a shortlist of rooftops that offer both drinks and entertainment.

Play Rooftop Games

Above the bar and concert venue at Reggie’s Live is the ‘Trainwreck Roof Deck,’ complete with a basketball hoop, pool table, bags boards, and 8 flat screen TVs to catch the game. Oh and if you get sweaty, you can wash off in their outdoor shower…encouraging Chicago to keep it clean out there.

The Royal Palms Shuffleboard Club is like a Florida vacation adjacent to the 606. Hop into Chicago's only shuffleboard club and enjoy a signature cocktail on the roofdeck, equipped with a full size, regulation shuffleboard court.

Streeterville Social is a seasonal rooftop lounge atop the Loews Hotel. Games include Giant Jenga, cornhole, and pétanque, the French rendition of bocce ball. If you’re tired you can grab a cocktail and relax in a swinging chair. Cindy's at the Athletic Association Hotel has stunning views, and the indoor game room is a quick elevator ride away.

Beer and Brats with a View

Grocery shopping is less of a chore when beer and brats are involved. Gene’s Sausage and Deli in Lincoln Square is a grocery store, sausage deli and sandwich shop with a seasonal rooftop Biergarten.

Listen to Live Music

Tanta in River North is serving up more than great food and piscos this summer. Listen to live music on Wednesday nights May through October on their inviting rooftop deck.

Bring the Dog

Every Wednesday night during warm months Joe’s on Weed has doggy happy hour on their rooftop (pup parents are also encouraged to attend). Table reservations are an option by contacting or 312.337.3486.

Rooftop Yoga

Yoga Under the Lights at Navy Pier, presented by VibeUp, is a summer rooftop yoga series in Streeterville. Shop at the Mindful Market starting at 5pm and choose from two yoga classes. The event takes place at the Navy Pier Rooftop Terrace, which has panoramic views of Lake Michigan and the Chicago skyline. This is a unique opportunity to do yoga under fireworks and be social. The nearby Hancock Building has also hosted yoga and mimosas, but that class is an indoor experience. If you're into rooftop yoga and boozy cocktails, head to Whiskey Business in Wicker Park.

Related: Chicago Brewery and Beverage-Infused Yoga Classes