Cocktails, champagne, and wine can be enjoyed among unmatched luxury as patrons take in sights of the Chicago River and the Wrigley Clock Tower from Trump International Hotel & Tower’s 16th-floor lounge. Meanwhile, adventurous drinkers can sample the bar’s freeze pops, such as the Sangria Rouge made from Syrah.
Twisted Spoke is an easy place to spot—it’s the biker-friendly diner with the half-buried motorcycles sprouting from its front garden. Past the restaurant’s pinball machine and biker-themed décor, the rooftop patio has several picnic tables where visitors can scarf down a “Fat Boy” burger, one of the city’s best.
From the 27th floor of the Wit Hotel, ROOF on theWit dazzles visitors with some of the city’s most memorable panoramic views. See the Marina City towers to the north, Lake Michigan to the east, and State and Lake Streets below. Iits outdoor fireplace and retractable glass ceiling make it a year-round destination and one of Travel + Leisure’s “hottest rooftop restaurants” in the world.
Bulls, Bears, and Blackhawks players have all been spotted at Market Bar, which is part-owned by White Sox GM Kenny Williams and features a rooftop that offers stunning views of the skyline from a mile west of the Loop. The rooftop area features plush booths where guests can enjoy upscale pub grub such as pizzas, angus burgers, or cheese plates.
When it first opened in 1982, Sidetrack offered beer cases as seating and didn’t even have a sign outside. Since then, the Boystown staple has grown to span eight storefronts and can host more than 1000 revelers at a time. Up on the bar’s massive multi-level rooftop, patrons can watch people stroll down Halsted while sampling one of the lounge’s boozy slushies.
The fusion of Latin and Asian influences can be seen not only throughout Sushisamba Rio’s chic Carnival-in-Tokyo décor, but also in its food and drink menus. While lounging on a low-profile couch, discerning drinkers can try cocktails made from cachaca, Brazil’s fermented sugarcane, or shochu, a Japanese distilled liquor.
Perched atop Hotel Lincoln, The J. Parker shares its name with a tragic figure—officer John Parker was assigned to guard President Lincoln on the night he was assassinated, but was off drinking at a nearby bar instead. Visitors of the rooftop lounge enjoy stunning, dichotomous views of verdant Lincoln Park and towering downtown. James Beard Award-nominee Chef Paul Virant assembled the menu of small plates, while the bar’s drink menu focuses on libations from Spain, Mexico, and Cuba.
Located on the top of Affinia Hotel’s 29th floor C-View feels like a hideaway in the clouds. Candlelit tables and views of the Hancock Tower create a romantic setting where patrons dine on the culinary creations of chef Nicole Pederson, who heads the lounge’s sister C-House restaurant.
Travel + Leisure chose Zed 451’s rooftop as one of “America’s Best Outdoor Bars” not just for its spectacular views of Near North, but also for its imaginative cocktails. Try a spiced strawberry margarita, infused with habanero simple syrup, or sip on the muddled fresh blueberries and mint in the Blueberry Gin Mojito. Each can be paired with selections from the upscale steakhouse’s lounge menu.
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