Cindy’s Rooftop

Cindy's Rooftop sits on the 13th floor of the Chicago Athletic Association hotel on South Michigan Avenue, beneath a glass atrium and beside an all-season terrace. The venue promotes sweeping views of Millennium Park and Lake Michigan, which make it a memorable place for a drink downtown.

It works as both a bar and a restaurant. Lunch is served from Monday to Friday until 2pm, and dinner from 5pm to 10pm, with a seasonal menu designed to go with the drinks list. The craft cocktails are the main event for most visitors, and the terrace, which is open all year, is the place to drink them when the weather allows. In colder months, the glass-roofed indoor space keeps the view without the wind.

Opening hours are 11am to 11pm from Monday to Thursday, 11am to midnight on Friday, 10am to midnight on Saturday and 10am to 11pm on Sunday. The rooftop occasionally closes early or entirely for private events, so check the website before going, particularly on weekday evenings. Reservations are encouraged and open up to 14 days in advance, and walk-ins are welcome when there is space.

Cindy's suits couples, groups of friends and visitors who want a drink with a view after a day of sightseeing. It is a natural stop after the Art Institute or Millennium Park, and it is popular at sunset and on summer evenings, so book ahead for those times. Prices are those of a central rooftop venue. Allow an hour for a drink, or longer for a meal.

For reservations and enquiries, call +1 312-792-3502 or email [email protected]. Timing makes a big difference here. Sunset is the most popular time, so book well ahead if you want to watch the light change over the park and lake, or come for lunch on a weekday for a quieter visit with the same view. In winter, check the weather and dress for the terrace if you plan to step outside, as it can be cold at this height.

Cindy's is in the Chicago Athletic Association building at 12 South Michigan Avenue, on the 13th floor. The Art Institute and Millennium Park are close by, so it is easy to combine with a day of sightseeing in the Loop. For live music afterwards, Buddy Guy's Legends on South Wabash Avenue is a short taxi ride away.