Here at Time Out, we’re constantly updating our restaurant and bar rankings to ensure we’re recommending the best that Chicago has to offer. This month, we’ve revisited our ranking of the best rooftop restaurants in Chicago, as well as the best bars in Chicago and the best restaurants in Chicago.
Based on our recent reporting, Cindy’s has risen to the number one spot and has been named our top rooftop restaurant in Chicago.

Yes, it’s touristy, and yes, it can be difficult to snag a reservation, but for very good reason. On every visit, we know there will be inventive cocktails, like the Stalk Exchange (vodka, caravedo pisco, falernum, arrack, lime, celery, and Scarborough bitters), top-notch contemporary American fare, and primo city and lake views from the 13th floor of the Chicago Athletic Association hotel.

A range of factors go into determining the rankings, and if you’d like to know more about that process, check out how we review at Time Out. The bottom line is that Cindy's truly embodies what we’re looking for when someone asks about the best rooftop restaurant in Chicago.
While we’re still always on the hunt for the hottest spots and shiniest hidden gems in Chicago, we also remember the classics like Cindy’s. Go forth, and enjoy a rooftop dinner at Chicago’s newly named best rooftop restaurant—and don’t forget to grab a skyline photo for Instagram.