Regine Rousseau, an award-winning author, speaker, and entrepreneur, is the founder of Shall We Wine. She has been featured on WGN Chicago, as well as other local TV broadcasts. She was also named one of “40 African American Tastemakers. She is a Level II certified Sommelier Guild.
She told the BBC that Chicagoans are grateful for rooftops because they have to endure the winter. “We go outside as soon as the weather is nice, even on a sunny winter day. We put our shorts and go outside.” If a restaurant has a rooftop or patio that is open in the winter months, we will go there.
Rooftop culture in the city is widespread and enthusiastic. “I have never been to another city where people would talk about going to a roof like it was a sporting event. It’s very serious around here.” Rousseau, a self-described “sky-hopper, scours the city’s roofs and wine lists to find the ideal backdrop for her client’s mile-high luxury event. Even Chicago natives appreciate the beauty of the city’s skyline.
Rousseau, a Chicago native who grew up in the city of Chicago, is not only a champion for nightlife but also for her hometown.
She said, “Chicago’s the best city in the entire world.” It’s a friendly town. You can ask questions to people. You can ask for recommendations. For example, “Oh, I am walking down the road; is there a good place to eat?” You can still find people who are happy to talk to you.
1. NoMI Garden, Park Hyatt: Best Overall.
Chicago has many posh roofs. But Rousseau’s favorite is NoMI Garden on the 7th floor of Park Hyatt Chicago, on the Magnificent Mile. She said, “That’s the one I like best.”
The decor is very minimalist. It’s bright, spacious, and has a beautiful, soothing scent. NoMI Kitchen is a dinner restaurant that’s completely enclosed in glass. It offers a stunning view of Lake Michigan, Chicago’s Water Tower, and the Chicago skyline.
NoMI’s carefully curated international wine list, including Laurent Perrier and Lyre Classico, is a favorite of the sommelier. She said, “It is my Champagne spot.” “It’s the place I go to explore their wine menu.”
She added, “It is a lovely space for Champagne conversations and to feel calm.” You get to see Chicago from above, but this is a quieter side of Chicago.
2. The best of Chicago: IO Godfrey Roofscape bar and lounge
The “Second City, America’s second city, has its own personality. It is known for combining Midwest charm and big-city sophistication. Rousseau says that this is the vibe embodied in its bars: “[It’s] Midwestern, with an East Coast Influence.” The vibe of the bar is “Come as you are, but please come right.”
The IO Godfrey Roofscape Lounge and Bar is where Rousseau finds the best “Chicago Vibes” in the sky. “Something is happening [there] every day.” You can’t just turn up. You’re going to [have] dress up just a bit.”
In the winter, the outdoor lounge offers igloos and firepits, so that guests can still enjoy the bar’s signature cocktail flights.
3. VU
Rousseau takes visitors to Chicago’s South Side, a vibrant, culturally diverse area of the city, which is bursting with avant-garde art galleries, colourful graffiti, and excellent restaurants. Rousseau lives in Bronzeville – a neighborhood historically known as Chicago’s ‘Black metropolis’.
The elegant VU rooftop restaurant is Rousseau’s favorite neighbourhood rooftop. The 13,000 sq ft bar/restaurant is located on the 22nd level of the Hampton Inn McCormick Place. It serves brunch dishes such as Chicago hot chicken with waffles. The restaurant and bar offer panoramic views over the South Side of Chicago, as well as the surrounding city. She said, “It is very accessible to downtown.” You’ll see tourists because of the McCormick Centre, but also a lot of South Siders. It’s an incredibly beautiful room, and the bar is huge. It’s comfortable with good music.”
Enjoy a relaxing rooftop lunch after an afternoon of shopping at Cindy’s, located on the 13th floor of the historic Chicago Athletic Association. (Credit Daniel Kelleghan photography)
4. Cindy’s is the best place to eat after shopping.
Cindy’s, overlooking Millennium Park and its “Bean” statue, is Rousseau’s favorite place to grab a tasty lunch after shopping.
Rousseau recommends a rooftop crawl, as many of the best rooftops in the city are located downtown. “Start early and have a wine, cocktail, or mocktail, at each location, to ensure you don’t get drunk by the end of your day.”
Her strategy is to “determine your age group and what vibe you are looking for.” I am a seasoned traveler, so I look for rooftops that have a lounge. I also want to drink great cocktails and wine. NoMI is important to me. London House and Cindy’s are two more. “If someone is younger, VU. That’s a young vibe. [Places on] State Street have a youthful vibe. [Like] The Wit. Beautiful venues.”
She said, “[It is] super cool since there’s a [lift] specific to that area.” It’s located in the Chicago Athletic Association building. So, as soon as you enter, Chicago’s history is all around. Built in 1890, the structure was once home to a member club that was one of Chicago’s most exclusive. They preserved the wood and all of the details. You feel something special about to happen when you walk into the space.
Cindy’s is located on the 13th floor of the historic site. It serves New American cuisine with dishes such as Pink Moon Oysters and truffle fries, and rainbow trout braised in cannellini bean sauce, arugula pistou, and chevre. They have excellent salads. It may sound boring, but I find it hard to find really good salads. “They [also] serve a delicious grilled cheese with tomato.”
Rousseau shared an insider tip. “If possible, try to get a balcony seat that looks out over Michigan Avenue and Lake Michigan… Do you know how your attitude changes when you enter a room? You might have been a little slumped, and you would say, “Wait! I’m in Cindy’s.”
Bryan at Alebrijes Agency
Pancho’s Rooftop Cantina is a fun Mexican bar that offers a low-key experience. (Credit to Bryan at Alebrijes Agency).
5. Panchos Rooftop Cantina is best for younger crowds
Chicago’s rooftop culture is dominated by upscale, classy establishments. Rousseau offers a low-key option with a sky-high view.
“[Panchos Rooftop Cantina!]” She said. It’s very casual. [If] you just want to be relaxed, then you can go here.”
The vibrant Mexican restaurant and bar occupies two floors. On the second floor, there is a rooftop with an open space, a muralled bar, a large margarita menu, and views of the South Loop’s skyline. The festive atmosphere is enhanced by happy hours and Mexican street foods like tacos and elote. “It is a younger crowd. If I remember correctly, they served in plastic cups. There’s loud music. [It’s] super different.”
