The sky is the limit for drinking and dining during the Chicago summers—literally. When the temperature finally rises, so does the elevation of the good-time seekers. Rooftops are the place to be to take in the views and the warm weather. From the highest heights to a little closer to earth, we’ve put together a list of the places you need to check off your rooftop bucket list while the summer lasts.
Cindy’s
Photo Credit: Photographye3.com | Fraiberg+Hollander
Fixed atop the Chicago Athletic Association Hotel, it’s no wonder this hidden gem calls itself the jewel in the crown of this gorgeous historic building. The view overlooking Millennium Park and Lake Michigan is only matched by the design and style of this indoor/outdoor space. A glass roof, exposed brick, and an abundance of natural light by day and ambiance by night set the scene perfectly for brunch, lunch, or even date night. The restaurant’s apothecary style drink menu adds a touch of whimsy to the experience while the made-to-share dishes on the menu will have you rethinking classic comfort food. Feeling a bit less formal? Head out to Cindy’s terrace overlooking the park and enjoy a boozy popsicle and some grownup summer fun.
12 S Michigan Ave, Chicago, IL 60603
LH Rooftop
Photo Credit: Nicholas James Photography
This multi-tiered rooftop at the intersection of Michigan Avenue and the Chicago River is a real multi-tasker. Above the LondonHouse Chicago you can take in the view from the 22nd floor’s outdoor terrace while exploring a seasonal menu of reimagined American dishes (think waffle fried duck) and classic cocktails. If you’re not up for dining al fresco, the 21st floor boasts equally stunning views and air conditioning. If you’re looking to raise the bar (literally), LH rents out the building’s crowning feature—the cupola—on the 23rd floor to let you rise above it all in an epic and intimate setting. This trio of options offer a prime spot to enjoy the summer and some lofty living.
85 E Wacker Dr, Chicago, IL 60601
The Roof at Joy District
Photo Credit: Joy District
If you like your rooftops with a little more bass, look no further than The Roof at Joy District on Hubbard. This clubby rooftop offers lounge seating, some swanky, urban art décor, and fun cocktails like rosé champagne poured over sorbet. The eclectic, fusion menu is a cut above the usual club grub with dishes like octopus tacos and ostrich meatball ramen. Add in a steady rotation of featured local and special guest DJ’s, and it’s the perfect spot to take in the Chicago nightlife under the stars.
112 W Hubbard St, Chicago, IL 60654
Cabana Club
Photo Credit: Adrian Gaut
What says summer in Chicago better than rooftop drinking and dining? How about drinking and dining poolside. Nestled in the middle of Chicago’s Wicker Park on the Robey Hotel’s sixth floor this elevated oasis with some tropical flair serves up the fruity drinks you’d expect—like their piña colada and frozen margarita—as well as some surprises—like a jalapeno-infused tequila shot. While the vibes may be tropical, the view is 100 percent Chicago. Take it all in, from the neighborhood sites and sounds to a breathtaking view of the downtown skyline.
2018 W North Ave, Chicago, IL 60647
FountainheadPhoto Credit: Fountainhead
Enjoy the summer sun away from the downtown crowds at this Ravenswood favorite. This local gastropub has a more laid-back vibe; however, its drink menu is anything but. The more than 25 beers on tap and 150-plus bottled beers and ciders may seem over the top until you look at their Scotch selection. Let’s just say it’s north of 300. If you’re an early riser (and assuming you didn’t test all the Scotch on Saturday), on summer Sunday’s you can get to the bar early for some namaste and mimosas with sunrise rooftop yoga led by Coconut Yoga.
