Cindy's Rooftop
3.8 ★ average from 5 reviews
Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.
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Recent reviews
- ★★★☆☆Megan Cole
Food is good but expensive. If you are in a hurry do not go here, as staff cannot give exact wait time. Appreciated the waiter, as soon as he found out we were in a hurry, got to go cups and boxes ready. As this was my experience I would not rule out coming back again … but for sure need to make sure to have at least 3+hrs before any travel. I gave 3 stars because of slow service and price of food for the amount you get. Lovely views of the Bean though.
- ★★★☆☆Mariela Mitchell
Cindy's Rooftop is one of those places where the view alone makes the visit worthwhile. The views overlooking Millennium Park and the Chicago skyline are absolutely beautiful and some of the best photos we took on our trip came from here. Unfortunately, the service left a lot to be desired. Almost all of the staff seemed overwhelmed, and as a result, friendliness and hospitality were pretty much absent throughout our visit. I understand that busy days happen, but it definitely affected the overall experience. The food was fine, but not particularly memorable. I ordered the Caesar salad and the duck pie. The salad was good enough, but the duck pie was a little dry. The cocktails were decent, although there was a green cocktail that was excellent and easily the highlight of the meal. I wish I could remember the name because it's definitely the one drink I'd recommend ordering. The inside of the restaurant was also quite loud, making conversation difficult at times. Still, if you're looking for an iconic Chicago view and a great place to take pictures, Cindy's Rooftop is hard to beat. Just go with the expectation that the scenery will likely be the highlight of the experience.
- ★★★★☆Jonathan Leonard
Cindy’s Rooftop is one of those spots that mostly lives up to the hype 🌆✨ The view is the real star overlooking Millennium Park and the Bean with the lake in the background. Even on a foggy day, it still feels like a whole experience and definitely gives that “Chicago moment.” Food was done well across the board: The burrata + figs was fresh, but felt unbalanced and under flavored Steak frites were cooked well with a good sear and flavorful Drinks were good, creative cocktail list and a solid wine selection, but nothing that completely blew me away. perfect for brunch, a date, or showing someone around the city. Overall: great experience with standout views, good food, and a strong atmosphere — just not quite perfect.
- ★★★★★Kate D'Albertanson
We had a beautiful dinner here. It's right beside the art gallery, which made for a lovely date night. The views, food, service and atmosphere were all incredible. It was a rainy, overcast day and still beautiful from up there. The acorn squash was our favourite. Melanie (the gm) was extremely responsive and helpful when responding to questions about my food allergies. Lots of gluten-free options! We will definitely be back. Thank you for the special evening.
- ★★★★☆JJ.X
We had a great experience at Cindy’s Rooftop. The view alone makes it worth the visit—absolutely stunning and the perfect for a relaxing lunch. If you are a rooftop explorer this is a must. As for the food, everything we ordered was delicious. The oysters were fresh and well-prepared, a great way to start the meal. The avocado toast was flavorful and nicely balanced, and the shrimp and grits were a standout—rich, comforting, and cooked just right. The only small downside was the elevator wait—it took a bit longer than expected to get up and down but once you’re there, it’s absolutely worth it. Overall, it’s the kind of place where the atmosphere and food come together perfectly. I’d definitely come back, especially for the views and the pretty inside settings.