Experience
Downtown Chicago's Best Rooftop Dining

atop the Chicago Athletic Association

Perched atop the 13th floor of the Chicago Athletic Association hotel under a glass atrium, Cindy's welcomes guests with sweeping views of Millennium Park, the ever-changing blues of Lake Michigan, and beyond. With vibrant service, an all-season terrace, and an extensive beverage menu that intertwines naturally with the dishes, every detail of your experience is thoughtfully crafted to make a lasting memory.

Modern restaurant interior with a high glass ceiling, wooden floors, and striped upholstered seating. The dining area features wooden chairs and tables set with plates and glasses, and large round hanging pendant lights illuminate the space. Exposed brick columns and green plants add to the contemporary, airy ambiance.

Dining area with a wooden table set for six, surrounded by wooden chairs, inside a brick-walled room with a fireplace decorated with large lanterns and a modern art portrait hanging above.

Hours

Reservations are encouraged and available 14 days in advance. Walk-ins welcome.

make a reservation

Monday - Thursday

11am - 11pm

Friday

11am - 12am

Saturday

10am - 12am

Sunday

10am - 11pm

Closed For Private Event

Monday, November 16th

closing at 3pm

Dining area with a wooden table set for six, surrounded by wooden chairs, inside a brick-walled room with a fireplace decorated with large lanterns and a modern art portrait hanging above.

About us

Celebrated rooftop restaurant & YEAR-ROUND terrace,
with sweeping views of Millennium Park, Lake Michigan, and beyond

Overhead view of a wooden table with five plates of diverse gourmet dishes including grilled chicken with vegetables and sauce, a braised beef dish garnished with nuts, pasta with cheese and greens, a plate with sliced bread and an egg, and a fresh vegetable salad with a lemon wedge, with two hands holding forks ready to eat.

Two smoked salmon bagel halves on a white plate with blue floral designs, topped with cream cheese, cucumber slices, and garnished with herbs, served on a wooden table with a striped napkin and fork, a small vase with yellow flowers, and a glass of orange juice.

Yellow-orange cocktail in a textured glass with a large ice cube, garnished with a purple and white orchid flower, next to a wooden menu with gold text.

Inspired food & drinks with
Remarkable Surroundings

Sweeping city views, year-round, from Chicago’s most inviting rooftop.

Dining area with wooden tables and chairs in a brick-walled room featuring a brick fireplace, hanging globe pendant lights, a skylight ceiling, and a framed art portrait above the fireplace.

Plate with four pieces of crispy fried chicken, sliced pickles, a small bowl of coleslaw, and a small bowl of dipping sauce, set on a wooden table with a striped napkin and two drinks, one with a lime slice and spicy rim.

A bartender grating a garnish over a tall glass cocktail filled with crushed ice, mint leaves, and a reddish liquid layer on top, placed on a bar counter.

Modern dining area with wooden floors, multiple tables set with plates and glasses, striped sofas in the center, and large floor-to-ceiling windows offering a clear view of a lake and blue sky.

Hand using metal tongs to place a dried pear slice garnish on a cocktail glass filled with ice and a pale yellow drink, on a metal bar surface next to a wooden menu labeled 'CINDY'S'.

Lobster roll sandwich garnished with fresh parsley and pickled onions, served with a grilled lemon half and a metal bowl of potato chips on a white plate.

Indoor rooftop bar with a long wooden counter lined with leather bar stools, behind it shelves filled with various bottles, decorative hanging globe lights, and a seating area with wooden tables topped with white napkins and small yellow flower vases.

Four assorted cocktails on a wooden table in a restaurant with a menu labeled "CINDY'S"; background shows wooden chairs and a cushioned bench by large windows.

A bowl of fresh tomato salad with chunks of red and yellow tomatoes, garnished with red onion slices, mint leaves, and placed on a wooden table. Nearby are tortilla chips in a bowl and a glass filled with a crushed ice drink garnished with a mint sprig, next to a small plate with food topped with parsley.

Dining area with wooden tables and chairs in a brick-walled room featuring a brick fireplace, hanging globe pendant lights, a skylight ceiling, and a framed art portrait above the fireplace.

Close-up of a colorful salad with mixed greens, cherry tomatoes, sliced watermelon radish, crumbled nuts, and dressing on a white plate with a blue rim, next to a cocktail glass with yellow drink and a purple orchid on a wooden table, with a person's hand holding a fork about to eat.

A bartender grating a garnish over a tall glass cocktail filled with crushed ice, mint leaves, and a reddish liquid layer on top, placed on a bar counter.

Modern restaurant interior with a high glass ceiling, wooden floors, and striped upholstered seating. The dining area features wooden chairs and tables set with plates and glasses, and large round hanging pendant lights illuminate the space. Exposed brick columns and green plants add to the contemporary, airy ambiance.

Hand using metal tongs to place a dried pear slice garnish on a cocktail glass filled with ice and a pale yellow drink, on a metal bar surface next to a wooden menu labeled 'CINDY'S'.

Smiling person holding a cheeseburger with lettuce, tomato, and melted cheese, sitting at a table with a glass of beer, fries, and a small metal cup of sauce.

Indoor rooftop bar with a long wooden counter lined with leather bar stools, behind it shelves filled with various bottles, decorative hanging globe lights, and a seating area with wooden tables topped with white napkins and small yellow flower vases.

Four diverse friends smiling and clinking glasses with colorful drinks and a glass of white wine outdoors in an urban setting on a sunny day.

A person adding drops of red liquid from a dropper into a yellow cocktail garnished with cilantro, on a bar counter.