Local, award-winning sommelier Regine Rousseau loves rooftop bars almost as much as she loves wine. From understated luxury to lively cocktail lounges, these are her top sky-high spots in the Windy City.
Nicknamed the “Windy City” and famous for its brutal winters, Chicago might not immediately seem like rooftop-bar territory. But for sommelier, media personality and events planner Regine Rousseau, rooftop culture is one of the city’s greatest pleasures.
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An award-winning writer, speaker and entrepreneur, Rousseau is the founder and CEO of Shall We Wine. She regularly appears as a wine expert on WGN Chicago and other local television programmes and was named one of the top 40 African-American Tastemakers. She holds a Level II certification from the International Sommelier Guild.
“We Chicagoans really appreciate a rooftop because we have to endure the winter,” Rousseau told the BBC. “The moment it’s nice outside – even if it’s just sunny – we’re putting on shorts and going out. And if a restaurant can open its rooftop during the colder months, we’ll still show up.”
Chicago’s rooftop culture, she says, is both enthusiastic and deeply ingrained. “I don’t know another city where people say ‘let’s go to a rooftop’ the way they talk about a sporting event. It’s serious business here.”
A self-described “sky-hopper”, Rousseau regularly scouts rooftops – and their wine lists – while curating luxury events for her clients. “Chicago has such a gorgeous skyline,” she said. “Even locals still get excited about seeing downtown from above.”
Beyond nightlife, Rousseau is also a passionate ambassador for her hometown. “Chicago is the greatest city in the world,” she said. “It’s friendly. People talk to you. You can stop someone on the street and ask for recommendations, and they’ll actually help. We love having visitors.”
Here are Rousseau’s five favourite rooftop bars in Chicago.
1. Best overall: NoMI Garden at the Park Hyatt
Chicago has no shortage of polished rooftops, but Rousseau’s top choice is NoMI Garden, located on the seventh floor of the Park Hyatt Chicago along the Magnificent Mile.
“That’s my favourite,” she said. “When you walk past the reception area and step into NoMI, it’s just… peace.”
The minimalist space is defined by dark woods, soft lighting and a calming atmosphere, while NoMI Kitchen – enclosed in floor-to-ceiling glass – offers sweeping views of Lake Michigan and the historic Water Tower.
Rousseau is particularly impressed by the wine list, especially its Champagne and sparkling selections, which include Laurent-Perrier alongside alcohol-free options like Lyre’s Classico.
“It’s my Champagne spot,” she said. “It’s where I go to really explore a wine list. You experience Chicago from above, but it’s a very quiet, refined side of the city.”
Website: nomichicago.com
Address: 800 Michigan Ave, 7th Floor, Chicago, IL 60611
Phone: (312) 239-4030
Instagram: @nomichicago
2. Best for Chicago vibes: IO Godfrey Roofscape Bar and Lounge
That energy shines at IO Godfrey, a lively rooftop in River North. “There’s always something happening,” Rousseau said. “People look good. You can’t just roll in you’ll want to dress up a little.”
The sleek, high-tech space features white lounge seating, a retractable roof and panoramic skyline views. In winter, guests can reserve igloos or gather around fire pits, making it a year-round destination for cocktail flights and happy hours.
Website: godfreyhotelchicago.com/i-o-rooftop-lounge
Address: 127 W Huron St at LaSalle, Chicago, IL 60654
Phone: (312) 374-1830
Instagram: @iogodfrey
3. Best for impressing out-of-town visitors: VU
Rather than steering visitors toward the heavily touristed Loop, Rousseau prefers to showcase Chicago’s South Side. “I’m a South Sider, through and through,” she said. Rousseau lives in Bronzeville, once known as the city’s “Black Metropolis”.
Her go-to neighbourhood rooftop is VU, a glass-walled lounge on the 22nd floor of the Hampton Inn near McCormick Place. The expansive space offers sweeping views and serves craft cocktails alongside brunch favourites like Chicago hot chicken and waffles.
“You get tourists because of McCormick Place, but also lots of locals,” Rousseau said. “It’s accessible, comfortable, has good music and an incredibly big bar.”
Website: vurooftop.com
Address: 133 E Cermak Rd, Chicago, IL 60616
Phone: (312) 256-2990
Instagram: @vurooftop
4. Best for a post-shopping lunch: Cindy’s
Overlooking Millennium Park and steps from downtown shopping, Cindy’s is Rousseau’s top pick for a leisurely rooftop lunch.
Located on the 13th floor of the historic Chicago Athletic Association building, the space blends preserved 19th-Century details with modern elegance. “The moment you walk in, you feel like something special is about to happen,” Rousseau said.
The New American menu features locally sourced dishes such as Pink Moon oysters, truffle fries and rainbow trout. “They also have amazing salads,” she added. “And the grilled cheese and tomato? Delicious.”
Her insider tip: “If you can, sit on the balcony overlooking Michigan Avenue and Lake Michigan. Your whole mood changes.”
Website: cindysrooftop.com
Address: 12 S Michigan Ave, Chicago, IL 60603
Phone: (312) 792-3502
Instagram: @cindysrooftop
5. Best for a younger crowd: Panchos Rooftop Cantina
While Chicago rooftops often lean upscale, Panchos Rooftop Cantina keeps things casual.
“It’s super easy and fun,” Rousseau said. “If you don’t want anything fancy, this is the place.”
Spanning two floors, the colourful Mexican bar features an open-air rooftop, mural-covered walls, an extensive margarita menu and views of the South Loop skyline. Expect plastic cups, loud music and a younger crowd, alongside Mexican street-food favourites like tacos and elote bites.
“It’s completely different from the others,” Rousseau said – and that’s exactly the appeal.
Website: panchoschicago.com
Address: 327 S Plymouth Ct, Chicago, IL 60604
Phone: (312) 362-1212
Instagram: @panchos.rooftop
