Top Chicago Rooftop Bars in the Summer Sun
Cocktail time takes a turn outdoors when the weather gets nice in Chicago. Look up at cocktail time to find some of Chicago’s best al fresco venues.
Aside from the fresh air, rooftop bars boast great views, and a perspective you don’t ordinarily get.
Here’s a short list of our favorites. Let us know about your neighborhood favorites. Our real estate group covers Chicago neighborhoods and suburban communities within a 50 mile radius of downtown.
2018 W North Ave, (The Robey), Chicago, Wicker Park
Tiny elevator whisks visitors to the 13th floor. This West Town location, a distance away from downtown, has incomparable views of the city.Tanta Chicago
118 W Grand Ave, Chicago, River North
Come for the sophisticated Peruvian cocktails and stay for dinner. Great treetop view of River North.
455 N Park Dr., Chicago, Streeterville
This third-floor oasis is a Zen zone. The large terrace divides into separate grassy areas offering giant Jenga, cozy swing chairs, and great views of the lake.
1750 N Milwaukee Avenue, Chicago, Bucktown
Fancy a bit of shuffleboard with your cocktail? Spacious, sunny, and hipster-approved rooftop playground offers it all.
ROOF on theWit
201 N State St, Chicago, Loop
A summer hotspot on the 27th floor of the Wit Hotel, with skyline views & upmarket cocktails.
Reggies Trainwreck Rooftop Deck Bar
2109 S State St, Chicago, South Loop
Laid–back sports bar with a roof deck and games features eight flat screens, a pool table, a Pop-A-Shot machine, cornhole, and picnic tables.
2101 N California Ave, Chicago, Logan Square
Sun-drenched rooftop serving Mexican food and beverages.
85 E Wacker Dr., The Loop
Exceptional views of the Chicago Skyline overlooking the Chicago River.
12 S Michigan Ave, Chicago, downtown
Hip, stylish rooftop bar overlooking Grant Park and Lake Michigan.
111 W Hubbard St, Chicago, River North
Swanky hangout with a downstairs bar plus a lounge & art deco New American supper club upstairs.
2 W Erie St., Chicago, Near North Side
The second highest rooftop bar in Chicago boasts inventively named and presented cocktails on its 27th floor lounge.
Some other options to consider if the weather isn’t quite so nice. These enclosed spaces offer year-round options for great drinks and to-die-for views:
Plymouth Restaurant & Rooftop Bar
327 S Plymouth Ct, Chicago, Printer’s Row
Three-level venue with year-round rooftop in the heart of downtown.
350 West Mart Center Drive, Chicago, Loop
Romantic 15th-floor bar with floor-to-ceiling windows showcase stunning views of the Chicago River and skyline.
52Eighty Rooftop Lounge
166 E Superior St, Chicago
Twenty-ninth floor luxe rooftop lounge offers indoor and outdoor seating.