As a city that loves its skyscrapers almost as much as it loves its alcohol, Chicago has no shortage of rooftop bars. Cindy’s is a consistent favorite among locals and visitors alike. Location-wise, it’s pretty optimally situated, right on Michigan Ave in the loop, overlooking Millennium Park and Lake Michigan beyond.
Perched atop the Chicago Athletic Association with a glass roof and an open terrace, Cindy’s is a picturesque destination for eating and drinking. They serve modern American fare for brunch and dinner, and have a lavish list of cocktails, wine and beer. Plus a bar snacks menu for those looking for lighter bites. But the draw is the view, and everything tastes better with a panorama of the rich blue lake in the horizon.
Go here for: golden hour drinks and bites
Order this: can’t go wrong with anything from their seasonally changing cocktail list
Amount of time to spend: probably an hour or two before it gets too scene-y
When to come: early-ish is better, it gets crowded out on that terrace
Getting here: the closest CTA stations are Washington/Wabash (green, orange, pink, brown, purple) and Monroe (red), also easily accessible via one of the many bus lines that go up and down Michigan.
Other things to note:
Last visited: August 2019
Last updated: December 2020