It’s rooftop season in Chicago, which means you’ll find locals lounging about for hours, eating and drinking on outdoor terraces perched high in the sky. But there’s no reason to settle for a simple beer and burger when reveling alfresco — the city has several swanky rooftop spots where you can sip on creative cocktails and dine on fine fare. Here are a few of our favorites.
Streeterville Social at Loews Chicago Hotel
This brand-new hot spot is also the city’s largest alfresco rooftop with some 9,000 square feet laden with grassy lawns, hanging birdcage seats and cabanas, a giant Jenga set and stellar views of the surrounding skyscrapers and Lake Michigan. Meticulously made cocktails can be had at one of two bars (try the signature Streeterville Mai Tai) as well as small plates like the crispy lamb belly gyro made with candied onion and feta tzatziki sauce. The party gets started after 4 p.m. daily — weather permitting, of course.
The Terrace at Trump
This ritzy spot is far from your standard outdoor patio. Soaring above most restaurants and lounges, The Terrace on the 16th floor of Forbes Travel Guide Five-Star Trump International Hotel & Tower Chicago has some of the area’s best views. You can see Lake Michigan and the Chicago River, but the most stunning sights you’ll eyeball are of the nearby Wrigley Building clock tower and the top of the famed Tribune Tower. The Terrace is adjacent to the Five-Star restaurant Sixteen, and its cocktail and food menus live up to the refined indoor dining experience. Our picks? The Banana Cognac (Courvoisier, Giffard Banane du Brésil, banana puree, fresh cane syrup, angostura bitters and Cannella) and the Trump Mojito (Flor de Caña rum, fresh cane syrup, hand-muddled mint and lime). And for food, go with the lobster maitake roll and one of the three decadent seafood towers.
Shanghai Terrace at The Peninsula Chicago
On the fourth floor of this Five-Star hotel sits Shanghai Terrace, a unique and impossibly chic alfresco lounge serving up skyline views, cocktails and dim sum. Asian-inspired drinks are the way to go when ordering — try the cucumber martini with fresh mashed cucumber, gin, ginger syrup and lime, or the Yi Zi coconut almond drink made with fresh coconut, rum, amaretto, soda, goji berries and anise. Light bites include vegetable spring rolls and sesame orange beef; the dinner menu features dim sum and traditional Cantonese dishes like braised tiger prawns and baby abalone with chicken.
The Dec Rooftop Lounge and Bar at The Ritz-Carlton, Chicago
At this Four-Star property, you’ll find revelers mingling on the stylish 12th-floor rooftop (known as “The Dec” to locals). Cushy sofas made for lounging, low-slung chairs and a marble-flanked fireplace elevate this outdoor space into something really special. The eats and drinks are nearly as memorable as the décor — the duck confit nachos and the doughnut sundae are particularly tempting. Don’t skip the lavish libations, which include our summertime favorite, the Mileena. This refreshing drink is made with white rum, rhubarb, lime and prosecco.