An incredible experience! We flew in from California for the holidays, and the views were absolutely stunning—Bean and lake views that truly did not disappoint. Friendly staff and good food. We'll definitely be back.
Van
My friend and I were quite excited to try out Cindy's since we've heard so many good things about the rooftop all over social media. We made a trip from Houston to Chicago centering around this for dinner. Unfortunately, the food is mediocre at best. We ordered the Truffle Parmesan fries, the Mushroom risotto, and the Steak Frites. For drinks, we ordered the Mionette "Alcohol removed" sparkling wine, the Drama Queen, and the Orchard Spritz. We did add the CBD to our cocktails. The good(ish): The presentation of all the food was pretty good, no complaints there. The fries overall were more or less fresh McDonald's fries with freshly shaved cheese on them. They were not particularly crispy, but at least they were fluffy. The truffle mayo dipping sauce was quite good, it was very balanced with a pronounced black truffle earthiness that went well with the fries. The Steak however, was very tender with a wonderfully smokey char, however I would've liked to at least have some cracked black pepper or flakey salt on it, as I felt it was a little under seasoned. As for the drinks, the wine was as expected. It was bright, refreshing, and paired well with our meal. The flavor of our cocktails was also excellent, with many nuanced flavors and great balance. Definitely worth. The bad: The mushroom risotto was very disappointing. When I hear mushroom, I expect to be able to at least taste some mushroom, but it was more like a standard cheese risotto that is whispering the word mushroom in your ear. It was pretty bland, even for risotto and even a little sprinkle of fresh BP would've helped. The brown butter hollandaise that is advertised with the steak was also very one-note, with no nuttyness that I expect when I hear brown butter. All I was able to discern from the sauce was clarified butter and the paprika sprinkled on top. It was also a lot fluffier than I expected, which resulted in much of the sauce not clinging to the steak unless I drowned the steak in the sauce.
Lesa
While on a women's bus trip we took a group of 10 to Cindy's during the holiday season. We chose Cindy's based off many positive reviews. The space was beautiful, food was delicious and making the reservation was easy. As a group of women who want to chat and are all 40+ we couldn't hear a thing because it was so loud. Everyone was having a great time, but we would have loved to be able to turn the volume down. Our server Eddie was very attentive, but visibly frustrated with us several times. Starting with our drink orders when we wanted to wait until we all had a minute to settle and ending with not allowing us to split the check more than 4 ways. I would absolutely recommend Cindy's, but know that it's loud and you will need to pay with one credit card.
Barbara
Really great food and such a thoughtful and helpful staff from the reception through the careful removal of the residue of the delicious lunch. Excellence throughout. Waiter was particularly charming which is consistent with our previous experiences at Cindy's.
Elsie
Server was very friendly and the view is breathtaking. The food was very mediocre. My friends and I all tried different dishes and no one thought their food was good.
Paola
An amazing location overlooking the Millennium Park Food was super cool and everybody was so kind to us. We are looking forward to coming back soon! Paola and Andrea
Bianca
Our first trip to Cindy's Rooftop was magical! Michelle was an amazing server and the food and drinks were top notch. The Heritage Brick Chicken is a stand out - the tastiest, juiciest cuts of chicken that I have ever had. No lie.
Trisha Lindsey
Stopped by for drinks and a view. Its beautiful.
Atmosphere: 5
Service: 5
Jemma Gibson
Super nice rooftop with a great view over Millennium park. Quick and friendly service too. Unfortunately the margarita was really poor, sweet and with no salt on the glass-pretty shocking for the price ($21). Cool pace to hang out, book for a table indoors for sure, don’t get the margarita.
Atmosphere: 5
Food: 3
Service: 5
Roger Hopper
Fun rooftop bar with creative and well-balanced cocktails and awesome views of downtown, Lake Michigan, and Millennium Park! Cool decor and architecture. Particularly enjoyed the Aphra-Cadabra cocktail (pictured). Can be busy, but pretty quick service despite this, bartenders are hustling to keep everyone happy!
Absolutely terrible waitlist system. Our party of 6 was waiting forever while smaller groups of 2–3 kept getting seated ahead of us for over 40 minutes, even after we were already #2 on the list. They kept saying there were no large tables available — but of course there wouldn’t be if they keep taking only small groups! We even offered to split into two smaller tables, but they flatly refused. The whole system made no sense and honestly felt discriminatory when refused seat separately. Extremely disappointing experience.
Atmosphere: 1
Food: 1
Service: 1
Ebelyn Soto
ofc really amazing view!! nice drinks :)
Atmosphere: 4
Service: 5
Emmanuel Enriquez
The service was great, the views were cool, but the food didn't quite hit the mark.
Our server, Blake, was very attentive and kind. He always aimed to make it right and did his best to make sure we were happy.
The view is unbeatable, and a must-see, especially if you're new to the city.
The food was mostly fine, except for the risotto. We ordered truffle fries, scallops, NY strip, and mushroom risotto.
The truffle fries were addictive, the scallops had a very interesting and unique sauce, and the NY strip had a good crust. But the prices were higher than expected, so the value isn't very strong.
While the mushroom risotto had a thoughtful presentation, the risotto itself wasn't prepared like risotto. It was more like watery rice, with a slight hint of mushroom. It was rushed and not given enough time or attention, which is a bummer especially considering it was priced higher than expected for risotto.
Overall, the food’s not really worth the price, but if you’re new to the city, Cindy's is worth stopping in for a drink and the view.
Atmosphere: 5
Food: 4
Service: 5
Doug Pilger
Love this place!!! Great place have some awesome drinks and food!!! Everything I've tried was delicious!
An incredible experience! We flew in from California for the holidays, and the views were absolutely stunning—Bean and lake views that truly did not disappoint. Friendly staff and good food. We'll definitely be back.
My friend and I were quite excited to try out Cindy's since we've heard so many good things about the rooftop all over social media. We made a trip from Houston to Chicago centering around this for dinner. Unfortunately, the food is mediocre at best. We ordered the Truffle Parmesan fries, the Mushroom risotto, and the Steak Frites. For drinks, we ordered the Mionette "Alcohol removed" sparkling wine, the Drama Queen, and the Orchard Spritz. We did add the CBD to our cocktails. The good(ish): The presentation of all the food was pretty good, no complaints there. The fries overall were more or less fresh McDonald's fries with freshly shaved cheese on them. They were not particularly crispy, but at least they were fluffy. The truffle mayo dipping sauce was quite good, it was very balanced with a pronounced black truffle earthiness that went well with the fries. The Steak however, was very tender with a wonderfully smokey char, however I would've liked to at least have some cracked black pepper or flakey salt on it, as I felt it was a little under seasoned. As for the drinks, the wine was as expected. It was bright, refreshing, and paired well with our meal. The flavor of our cocktails was also excellent, with many nuanced flavors and great balance. Definitely worth. The bad: The mushroom risotto was very disappointing. When I hear mushroom, I expect to be able to at least taste some mushroom, but it was more like a standard cheese risotto that is whispering the word mushroom in your ear. It was pretty bland, even for risotto and even a little sprinkle of fresh BP would've helped. The brown butter hollandaise that is advertised with the steak was also very one-note, with no nuttyness that I expect when I hear brown butter. All I was able to discern from the sauce was clarified butter and the paprika sprinkled on top. It was also a lot fluffier than I expected, which resulted in much of the sauce not clinging to the steak unless I drowned the steak in the sauce.
While on a women's bus trip we took a group of 10 to Cindy's during the holiday season. We chose Cindy's based off many positive reviews. The space was beautiful, food was delicious and making the reservation was easy. As a group of women who want to chat and are all 40+ we couldn't hear a thing because it was so loud. Everyone was having a great time, but we would have loved to be able to turn the volume down. Our server Eddie was very attentive, but visibly frustrated with us several times. Starting with our drink orders when we wanted to wait until we all had a minute to settle and ending with not allowing us to split the check more than 4 ways. I would absolutely recommend Cindy's, but know that it's loud and you will need to pay with one credit card.
Really great food and such a thoughtful and helpful staff from the reception through the careful removal of the residue of the delicious lunch. Excellence throughout. Waiter was particularly charming which is consistent with our previous experiences at Cindy's.
Server was very friendly and the view is breathtaking. The food was very mediocre. My friends and I all tried different dishes and no one thought their food was good.
An amazing location overlooking the Millennium Park Food was super cool and everybody was so kind to us. We are looking forward to coming back soon! Paola and Andrea
Our first trip to Cindy's Rooftop was magical! Michelle was an amazing server and the food and drinks were top notch. The Heritage Brick Chicken is a stand out - the tastiest, juiciest cuts of chicken that I have ever had. No lie.
Stopped by for drinks and a view. Its beautiful.
Atmosphere: 5
Service: 5
Super nice rooftop with a great view over Millennium park. Quick and friendly service too. Unfortunately the margarita was really poor, sweet and with no salt on the glass-pretty shocking for the price ($21). Cool pace to hang out, book for a table indoors for sure, don’t get the margarita.
Atmosphere: 5
Food: 3
Service: 5
Fun rooftop bar with creative and well-balanced cocktails and awesome views of downtown, Lake Michigan, and Millennium Park! Cool decor and architecture. Particularly enjoyed the Aphra-Cadabra cocktail (pictured). Can be busy, but pretty quick service despite this, bartenders are hustling to keep everyone happy!
Atmosphere: 5
Food: 5
Service: 5
Restaurantji Recommends
Absolutely terrible waitlist system. Our party of 6 was waiting forever while smaller groups of 2–3 kept getting seated ahead of us for over 40 minutes, even after we were already #2 on the list. They kept saying there were no large tables available — but of course there wouldn’t be if they keep taking only small groups!
We even offered to split into two smaller tables, but they flatly refused. The whole system made no sense and honestly felt discriminatory when refused seat separately. Extremely disappointing experience.
Atmosphere: 1
Food: 1
Service: 1
ofc really amazing view!! nice drinks :)
Atmosphere: 4
Service: 5
The service was great, the views were cool, but the food didn't quite hit the mark.
Our server, Blake, was very attentive and kind. He always aimed to make it right and did his best to make sure we were happy.
The view is unbeatable, and a must-see, especially if you're new to the city.
The food was mostly fine, except for the risotto. We ordered truffle fries, scallops, NY strip, and mushroom risotto.
The truffle fries were addictive, the scallops had a very interesting and unique sauce, and the NY strip had a good crust. But the prices were higher than expected, so the value isn't very strong.
While the mushroom risotto had a thoughtful presentation, the risotto itself wasn't prepared like risotto. It was more like watery rice, with a slight hint of mushroom. It was rushed and not given enough time or attention, which is a bummer especially considering it was priced higher than expected for risotto.
Overall, the food’s not really worth the price, but if you’re new to the city, Cindy's is worth stopping in for a drink and the view.
Atmosphere: 5
Food: 4
Service: 5
Love this place!!! Great place have some awesome drinks and food!!! Everything I've tried was delicious!
Atmosphere: 5
Food: 5
Service: 5
Great views of Lake Michigan
Atmosphere: 5
Food: 5
Service: 5
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