No matter the season, there is always something to do in Chicago. From vibrant street festivals and live concerts in the summertime to sporting events, delectable world-class dining experiences and strolls along the Magnificent Mile throughout the year. In short, the Windy City has something for everyone—especially imbibers.
As a native of the Chicagoland area and wine culture expert, I’ve had the pleasure of hitting various spots across the city for glasses of wine and elegant cocktails. In addition to a solid wine and cocktail menu, I classify a good rooftop bar as one with a welcoming vibe, cozy decor, top-notch food and drink offerings, groovy playlists and, of course, an impeccable view of one of the most mesmerizing skylines in the world.
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While rooftop bars in Chicago are often thought of as being best enjoyed during the warmer months, I’m here to confirm that here in the City of Wind, they’re available for patronage all year round. Whether you are on the northside, downtown or in the West Loop, there are rooftops to sip the day (and night) away.
To help me compile a list worthy for any eager and thirsty Chicago tourist, I’ve asked a few of the city’s most in-the-know beverage and hospitality experts to share their favorite rooftops and what they believe makes them special. In no particular order, here are eight rooftop bars that are worth visiting next time you are in Chicago.
NoMI Kitchen at the Park Hyatt Chicago (Streeterville)
Regine T. Rousseau, founder of marketing company Shall We Wine, Inc., is a self-proclaimed “sky bar” hopper, and has visited rooftop bars all over the world. “I can say with confidence that no other city in the world does celestial drinking like Chicago,” Rousseau states. She believes that NoMI’s rooftop is the top place to see and be seen. “There’s always interesting Champagne by the glass, and in terms of food they have one of the best burgers in the city.”
VU Rooftop Bar (South Loop)
Located right next door to McCormick Place, VU Rooftop Bar is an indoor rooftop that provides patrons with a 360-degree view of the city. I absolutely love the South Loop, and VU has plush and chic decor that makes you want to hang out for more than just one drink. Cocktails include updated twists on classics like the Uncle’s in New Orleans, a potent mixture of rye, Cognac, bitters and simple syrup infused with anise and cardamom that the menu describes as the “Sazerac of your dreams.”
ROOF on theWit (Downtown)
If you’re looking for a glam rooftop experience, this lounge, located 27 stories above State Street, is for you. With options for both daytime and evening adventures, ROOF on theWit also has an impressive dining menu, with dishes like truffle and burrata pizza and shrimp tempura sushi rolls. There’s a way to do ROOF on different budgets—bottle service for the high rollers, but also a notable happy hour with $12 French martinis and house sangrias.
I|O at The Godfrey (River North)
As the largest rooftop in Chicago, I|O is open all year round. “I|O is massive, I haven’t really seen anything quite like it in the city,” says creator and founder of Chicago Food Scene Leslie McConneIl. “Whether it’s raining or cloudy you will still have views on top of views. They have several different sections and they’re all cozy, with different beautiful views of the city.” Opt for sippers like the barrel-aged negroni or the Amythyst Destiny, a purple-hued stunner thar marries vodka and St-Germain.
Cindy’s Rooftop (Downtown)
Visiting Cindy’s is a must for those with even a passing interest in Chicago hospitality. “I love Cindy’s at the top of the Chicago Athletic Association,” says Ari Bendersky, writer and author of the Something Glorious with Ari Bendersky substack. “The view overlooking Millennium Park and Lake Michigan is unparalleled and shows locals and visitors a glimpse of the city’s history while also soaking up all its beauty.” Bendersky recommends starting with oysters and a cocktail like an Oaxaca Old Fashioned or a glass of crisp dry Provençal rose.
Cloud Bar at 360 (Downtown)
Located on the 94th floor of the John Hancock Observatory, this spot is a celebration of Chicago’s 77 unique neighborhoods. The cocktails are homages to specific areas—for instance, the Wild and Personable, a cucumber vodka-based concoction with strawberry puree and jalapeño with a tajin rim, is inspired by the vibrant and diverse Lakeview enclave. Many drinks also come in tilted glasses—yes, tilted—a nod to the observation deck’s harrowing TILT Ride. Entry to the bar requires a ticket purchase, but with views like this, who can complain?
Selva (Fulton Market)
Tucked away from the hustle and bustle of Downtown, Selva resides on the seventh floor of The Emily Hotel in the heart of the West Loop’s Fulton Market district. This chic, Mexican-inspired bar offers handcrafted cocktails with an emphasis on tequila and mezcal—they make a mean, authentic margarita—and real-deal, south-of-the-border fare like pork carnitas tacos and yuca fries topped with smoky barbacoa.
Devereaux (Gold Coast)
On the 18th floor of the Viceroy Hotel, which also happens to be the pool deck, Devereaux offers hearty share plates and inventive cocktails against a breathtaking view. Though currently closed for renovations, it’s poised for a spring of 2024 reopening—just in time to enjoy the poolside city views as the weather warms up. Nosh on shareable plates like the beer-battered cod tacos crowned with smoked trout roe, or opt for the salmon ceviche studded with mango, Fresno chiles, sesame and sriracha aioli. For drinks, go for sippers like the tropical Hollaback, which combines plantain-washed Cognac with banana liqueur and bitters, or on steamier nights, the rotating seasonal frosé.
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Published: April 19, 2024
