Cindy's Rooftop
Dine with a 4.4-star view at this iconic Chicago rooftop. Enjoy crafted cocktails and a vibrant atmosphere. Discover why it's a must-visit spot.
Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.
About Cindy's Rooftop
Perched high above the bustling city, this popular Chicago establishment offers a truly memorable dining experience. Diners consistently praise the stunning panoramic views of the park and skyline, which create a uniquely special atmosphere. The venue, with its nod to historical charm in the hotel foyer below, provides a sophisticated yet inviting setting for enjoying well-prepared cocktails and delicious food. It's a favorite spot for both groups and those seeking a lively ambiance, with outdoor seating available to further appreciate the city's beauty. The attentive service complements the overall experience, making it a standout destination.
Restaurant Analysis
Restaurant Characteristics
This restaurant has been analyzed using our formula-based system to help you understand its key features and match it with your dining preferences.
Price Range (Upscale)
Upscale dining ($$$) - Fine dining with premium prices
Meal Time (dinner)
This restaurant primarily serves dinner. Based on opening hours.
Group Size (Groups Welcome)
Welcomes large groups and families. Great for group dining.
Atmosphere (Outdoor)
Al fresco dining with outdoor seating
Dining Style (Flexible)
Flexible options. Reservations available but not required.
Features & Amenities
This restaurant offers: Outdoor Seating, Cocktails, Beer, Wine, Coffee, Groups Welcome, Reservations
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Why Travelers Love Cindy's Rooftop
Sourced from recent guest feedback and verified reviews.
What a great spot. We only had drinks, but the atmosphere was great. We hung out for a good while and before leaving took in the fab view. Before you go all the way up, walk up one flight of stairs and take in the hotel foyer. Full of history. It used to be a male only club. Fantastic features. Cindy’s Rooftop has a beautiful panoramic view over Chicago and the park, which makes the atmosphere feel special and memorable. The drinks were well prepared and the staff stayed friendly and attentive the whole time. Even though the place can get busy, the service didn’t feel rushed or chaotic. Prices are higher than average, but the view and the overall vibe make the experience worth it. It’s a great spot for photos, casual celebrations, or just enjoying the city from above The rooftop in Chicago is definitely a place worth visiting. It has incredible views and a very, very pleasant design. The service is correct, and the food is just okay — nothing special — but that’s not really the point. What truly makes it stand out is the atmosphere: the views, the design, and the overall vibe of the place are amazing. It’s absolutely worth going at least once to enjoy the experience and take in the city from above
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Recent Reviews
Seamus M.
November 3, 2025
What a great spot. We only had drinks, but the atmosphere was great. We hung out for a good while and before leaving took in the fab view. Before you go all the way up, walk up one flight of stairs and take in the hotel foyer. Full of history. It used to be a male only club. Fantastic features.
Masherins G.
November 8, 2025
Cindy’s Rooftop has a beautiful panoramic view over Chicago and the park, which makes the atmosphere feel special and memorable. The drinks were well prepared and the staff stayed friendly and attentive the whole time. Even though the place can get busy, the service didn’t feel rushed or chaotic. Prices are higher than average, but the view and the overall vibe make the experience worth it. It’s a great spot for photos, casual celebrations, or just enjoying the city from above
Salvador T.
October 20, 2025
The rooftop in Chicago is definitely a place worth visiting. It has incredible views and a very, very pleasant design. The service is correct, and the food is just okay — nothing special — but that’s not really the point. What truly makes it stand out is the atmosphere: the views, the design, and the overall vibe of the place are amazing. It’s absolutely worth going at least once to enjoy the experience and take in the city from above
adriana C.
September 9, 2025
Delicious food and generous portions — we tried the salmon, meat, and a roasted carrot starter, all outstanding. The atmosphere is great, and the rooftop view over Millennium Park is spectacular. You can grab a drink without a reservation, but I recommend booking ahead for the restaurant. Definitely worth the visit!
Kyuwon L.
October 21, 2025
Gorgeous roof restaurant attached by an open-roof terrace looking over the park and lake. Their dishes are pretty average and servers tend to rush you through your ongoing meal but you don’t expect the highest qualities of foods or hospitality from a place like this so I’d say it’s still pretty acceptable. Go for the view and the vibe.
What to Expect
Features and amenities that make Cindy's Rooftop special
Outdoor Seating
Cocktails
Beer
Wine
Coffee
Groups Welcome
Reservations
Practical Information
Everything you need to know before you visit
Payment Options
Parking
Accessibility
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Transportation Tips
Excellent public transportation with L trains, buses, and Metra. Walking is perfect for exploring downtown, and ride-sharing services are widely available.
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