Cindy’s Rooftop
Cindy’s ranks at sixteen rather than lower because the combination of the room, the view, and a drinks program sophisticated enough to hold its own without the backdrop is genuinely rare.
Perched above the historic Chicago Athletic Association building on Michigan Avenue, Cindy’s has a view that is not subtle: Millennium Park sprawls directly below, the lake extends east, and the skyline builds to the south. The indoor/outdoor design handles Chicago weather with floor-to-ceiling windows that make the greenhouse feel functional in shoulder season rather than aspirational. The cocktail list runs to large-format apothecary vessels and a spirit-free program that matches the ambition of the main list.
The crowd is mixed — hotel guests, out-of-towners who’ve done their research, locals who’ve figured out that a reservation on a Wednesday costs the same as Saturday and feels entirely different. Time Out named it Chicago’s best rooftop, which is correct on the view and nearly correct on the drinks. Arrive before sunset in summer and do not leave before the Millennium Park lights come up.
- A large-format apothecary cocktail
- A spirit-free seasonal pour
- A glass of biodynamic wine at sunset
