Park and Lake Views From Above
Cindy's sits on the 13th floor of the Chicago Athletic Association on Michigan Avenue, and the view across Millennium Park is the room's defining feature. The rooftop burger and seasonal flatbread anchor the food menu, with craft cocktails doing the heavier lifting. It runs as a destination for drinks-and-views rather than a destination for the kitchen alone. Date night and out-of-town guests make up a reliable share of the crowd on any given evening.
Cindy's Rooftop sits on top of the Chicago Athletic Association hotel, and the trip up is part of the experience. An elevator operator takes diners straight to a glass atrium with sweeping views of Millennium Park, the skyline and Lake Michigan. Diners describe a lively mood, close tables and a crowd that fills the bar.
The menu leans toward sandwiches and burgers, with oysters, fried chicken, steak, a fish sandwich, a beet salad, rigatoni and a mushroom risotto also named. Vegetarian diners found good plates, and the cocktails are called interesting. Many diners say the drinks and the view are the main event, with the food a pleasant bonus.
Practical advice is straightforward. Reservations are hard to get, so book several days ahead, and do not arrive early, since the table will not be ready. The bar takes walk-ins. A surcharge applies to checks, including at both the bar and the table. The room is loud, and interior tables do not always face the park, so daytime visits show the views best. A few diners reported poor service, but plenty praise attentive staff.