Make it a crawl
Many of the city’s best rooftops are located downtown, so Rousseau suggests a crawl: “Start early, maybe have wine at one, a cocktail at another, a mocktail at the third, so you’re not drunk at the end of the day.”
Her strategy: “Figure out your age category, what vibe you’re looking for. I’m well-seasoned, so I’m looking for rooftops with a lounge; I want great cocktails, great wines. NoMI, because that’s super important to me. London House is another one, and then Cindy’s. If someone’s younger: VU; that’s a younger vibe; [places on] State Street offer a younger vibe [like] The Wit – beautiful venues.”
“[It’s] super cool because there’s a specific [lift] that goes there,” she said. “It’s in a historic building, the Chicago Athletic Association, so right when you walk in, it’s all about Chicago history.” The structure, built in 1890, was once home to one of the city’s most exclusive members clubs. “They preserved the wood and all the details. You’re automatically walking into a space that you feel like something special is about to go down.”
High up on the 13th storey of the historic site, Cindy’s serves elegant New American cuisine featuring locally-sourced dishes like Pink Moon Oysters, truffle fries and rainbow trout with braised cannellini beans, arugula pistou and chevril. “They have great salads. I know that it sounds boring…but it’s hard to find a really good salad to me. They [also] have a grilled cheese and tomato that is delicious.”
Rousseau offered an insider tip: “If you can, get a seat on the balcony that overlooks Michigan Avenue and Lake Michigan … You know how you walk into a space and all of a sudden your attitude changes? If you were kind of slumped over, you’re like, ‘Wait, I’m at Cindy’s.'”
Website: https://www.cindysrooftop.com/
Address: 12 S Michigan Ave, Chicago, IL 60603
Phone: (312) 792-3502
Instagram: @cindysrooftop
