Chicago Rooftop Bars
Drinks on Top of the World

Rising from the ashes of the Great Chicago Fire of 1871, Chicago became fertilized by architectural ingenuity and eventually sprouted an iconic skyline that many consider to be the country’s best. Today, the city is rife with rooftop bars where one can take in spectacular views of sky-reaching towers, sparkling waters, and the concrete canyons found in between.
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River North: Fireworks on the River

The glow of the city provides all the light you need for sipping cocktails on the terrace patio of the Trump Tower—not that the burst of twice-weekly fireworks isn't a welcome touch. When the weather gets hot, the house serves alcoholic freeze pops in flavors such as passion colada or limoncello and strawberry jus.

Near North: Imaginative Cocktails

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.

West Town: Burgers and Beer List

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.

The Loop: Retractable Roof on 27th Floor

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.

Gold Coast: Speakeasy-Style Lounge

Drumbar’s website says it “takes ‘speakeasy’ to the next level, 200 feet up to be exact.” The bar serves bourbon and whiskey-based cocktails at the top of the posh Raffaello Hotel, which was built in 1925.

West Town: Athlete Hotspot

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.

Lake View East: Slushie-Fueled Partying in Boystown

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.

River North: Flavors of Peru, Brazil & Japan

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.

Old Town: Lincoln Park Views

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.

Gold Coast: Candlelit 29th-Floor Hideaway

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.

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