Cindy's Rooftop

Cindy's (Chicago Athletic Association, 13th floor)

Glass-roofed rooftop above Millennium Park and the lake

⚠ Book; slots open 14 days out

Hours

Mon–Thu 11am–11pm, Fri 11am–midnight, Sat 10am–midnight, Sun 10am–11pm (official site, Oct 2026)

Budget

$30–50 for a cocktail or two (check on site)

Address

13th floor, Chicago Athletic Association, 12 S Michigan Ave

The 13th floor of the Chicago Athletic Association, an old athletic club turned hotel. Long wooden tables sit under a glass atrium roof, and out on the terrace Millennium Park and the Bean spread below with Lake Michigan beyond. Sunlight at brunch, city lights at night, and it's a favourite for a date or a last-night drink.