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. 


Up Room

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.


Streeterville Social

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.


Royal Palms

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.


Lonesome Rose

2101 N California Ave, Chicago, Logan Square

Sun-drenched rooftop serving Mexican food and beverages.


London House

 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.


Apogee Lounge

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.


Cityscape Bar

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.