Fancy a sophisticated evening above Chicago’s twinkling highrises? Looking for a taste of the tropics? Care to mingle with fellow wine lovers? Want a low-key hipster vibe? Whatever your pleasure, Chicago’s booming rooftop scene offers. In the past year, a bevy of new arrivals joined the standbys. The result? High-altitude happiness. Whether you expect fanciful cocktails or tastes straight from Asia, glass roofs or sky-high pools, the secret’s out: During the Windy City’s all-too-brief mild months, locals like to get down from up high.
Noyane: The rooftop of the Conrad Chicago hotel has been transformed into a plush, warm-weather oasis. Noyane emphasizes sushi, skewers, shareable apps, and wagyu beef. And incredible cocktails—such as a sake sangria; a delicate blend of sake, sparkling wine, grapes, watermelon, and eau de vie. Originally conceived as a Japanese-Latin fusion venue, Executive chef Jordan Dominguez insisted that straight Japanese would better suit the Chicago market. Unlike other rooftops that stretch the seasons with heaters and ceilings, Noyane's open-air layout means that its peak months are fleeting: Better hurry.
Apogee: Perched atop the Dana Hotel, Apogee is pure whimsy. Locally produced custom glassware in the shapes of toadstools, edible butterflies, and torched marshmallows dipped in anise and coconut ash: the Chicago Tribune says that Apogee is "serving the most fun cocktails in Chicago this summer." You must taste the genius of mixologist Benjamin Schiller. Try the Where Do You Summer?, a complex blend of El Dorado rum, Falernum, grapefruit, Maraschino, Tiki bitters, and pumpkin spice. Better yet, cozy up to the large-format beverages, serving 2-4 people out of breathtaking glass vessels. The Fifty/50 Restaurant Group’s new spot doesn’t skimp. Expect mohair couches and a marble bar, as if you weren’t sold at the cocktails alone. You might love Apogee enough to move in, but CONLON / Christie's International Real Estate can help you with the next best thing—moving into a beautiful property nearby. Check out 1500 North Lake Shore Drive, a historically significant 10,000 square-foot duplex with 19 windows that offer unadulterated Lake Michigan views.
Cabana Club: The Robey Chicago’s rooftop is hip. Refined, maybe. Cool, absolutely. Chicago Magazine calls it “The Casual Rooftop Bar of Your Dreams.” That doesn’t mean the place skimps on style. With nautical striped upholstery, exposed brick, a shallow pool, and sweeping views of Wicker Park, Cabana Club stands up to the thoughtful, polished Midcentury aesthetic of the Robey itself. Cabana Club’s Mexican-inspired menu refreshes: Try a classic Paloma with tequila, grapefruit, and soda water. Pair that with a camaronesor elote tostada, and you’ve got yourself a fiesta. While you're in the neighborhood, make it your home! Check out the 4-bedroom, 4,400 square-foot contemporary family at 1720 West Pierce Avenue.
Boleo: It seems impossible, but someday, summer will end. Take comfort in Boleo, a South American restaurant and bar in the Financial District that has the good sense to encase its rooftop in glass. It’s a year-round taste of the tropics, Try Latin American street food such as beef empanadas with hard-boiled eggs, citrus, and cilantro. Or a vibrant whitefish ceviche. Wash that down with a Chilcano—infused Pisco with ginger and carbonation in flavors such as guava and strawberry, coconut and lemongrass, or pineapple and cinnamon. Bold palates will appreciate an Argentinian favorite: the Fernet and Cola.
Cindy’s: It’s a rare and jaded visitor who isn’t floored by Cindy’s stunning views of Millennium Park. Perched atop the Chicago Athletic Association, this crown jewel has been making people happy to be elbow-to-elbow since it opened in 2015. Try the lavender-colored Grey Garden, a blend of Tito’s, Dolin Blanc, Crème de Violette, jasmine tea, and lemon. No alcohol? No problem! Try Frog Greishaw’s cult-favorite kombuchas in flavors such as raspberry-chocolate mint. Hearty eaters will rejoice at the menu’s fortifying duck breast, striploin, and charcuterie. There’s something for everyone at Cindy’s.
Mahalo: If ever there were a Chicago restaurant built for summer, Mahalo is it. The white clapboard of this Hawaiian-themed Wicker Park haunt can feel wistful when the mercury drops, but during the dog days, Mahalo’s one of the best places to unwind. The rooftop boasts surfboards and grass umbrellas. And the menu? Poké bowls, Hawaiian Ramen, fish tacos, a shredded Kalua pork sandwich. On the drink program, find the Gin Aku, gin with apricot liquor, pineapple juice and mint. Or the Mo’Betta with Buffalo Trace, Aperol, guava purée, lemon juice, and mint. The Daily Daiquiri? Can’t go wrong.
Make the rounds before the leaves fall. Whether you want classic Japanese fare at Noyane, the whimsical mixology at Apogee, the mellow party at Cabana Club, a taste of Latin America at Boleo, kombucha and views at Cindy’s, or a Big Island vibe at Mahalo, Chicago’s summertime rooftop spots won’t disappoint. With all of these wonderful options, we advise clearing your calendar.