Cindy's rooftop at The Chicago Athletic Association Hotel Verified listing

Cindy’s Rooftop at The Chicago Athletic Association Hotel is one of the city’s most sought-after dining spots, offering stunning panoramic views of downtown Chicago, including a prime view of Millennium Park and the iconic skyline. Located atop the historic hotel, this rooftop bar and restaurant boasts a chic and inviting atmosphere with floor-to-ceiling windows, a lush indoor-outdoor space, and cozy seating areas. Whether you're visiting for a casual afternoon cocktail or a celebratory dinner, Cindy’s provides an unforgettable setting, particularly at sunset or as the city lights come to life in the evening.

The menu at Cindy’s Rooftop is an inventive blend of contemporary American cuisine with Mediterranean influences, perfect for sharing or indulging in a more intimate meal. Guests can enjoy a range of dishes, from light and fresh salads and seafood offerings to heartier options like roasted chicken and steak frites. The rooftop’s wood-fired grill also features delicious grilled vegetables and meats, adding a smoky, flavorful twist to the menu. Cindy's also offers an impressive cocktail list with creative drinks, crafted with seasonal ingredients and local spirits. The carefully curated wine and beer selections complement the meal, ensuring a well-rounded dining experience.

With an impressive 4.5-star rating, Cindy’s Rooftop is known for its exceptional food, stellar cocktails, and incomparable views. The combination of outstanding service and the unique rooftop setting makes it a popular choice for both locals and visitors. Given its popularity, especially during warm weather months, it’s advisable to make a reservation, particularly for weekend evenings or special events. Whether you’re looking to enjoy a casual brunch, a sunset drink, or a full dinner with a breathtaking view, Cindy’s Rooftop offers a memorable experience that highlights the best of Chicago’s dining scene.