Cindy's Rooftop

Perched on the 13th floor of the Chicago Athletic Association, Cindy’s remains one of the most popular spots for taking in the city. The bright and airy restaurant pairs sweeping views of the skyline and lake with a menu that’s solid, if not particularly memorable. It’s worth braving the crowds for a drink, but an hour-long wait might be too much for some to justify.

The vibe: Cindy’s has a lively, polished feel, with a stylish dining room bathed in natural light thanks to floor-to-ceiling windows and expansive skylights. The open-air terrace overlooks Millennium Park, offering impressive sights, while the guests are a mix of tourists and locals.

The food: The seasonal menu leans toward approachable American fare with globally-inspired touches. At dinnertime, expect shareable dishes ranging from mussels and branzino to fried chicken and ribeye. Weekend brunch brings options like chilaquiles and shrimp and grits.

The drinks: The cocktail list features refreshing, easy-sipping concoctions such as the Second to None, made with gin, pomegranate cordial, genepy, lemon and honey. There are also spirit-free creations, mimosa kits, beer, wine and teas from Rare Tea Cellar.

Time Out tip: Cindy’s gets busy, especially during peak hours, so make a reservation to avoid the line.