I’ve been to Cindy’s Rooftop multiple times, and it never fails to amaze me—but the most unforgettable visit was when I went with my girlfriend for one of the best and most romantic dinners we’ve ever had.
Everything about this place is pure magic. The unobstructed view of The Bean, the water, and the Chicago skyline creates an absolutely breathtaking backdrop, especially at sunset when the city is glowing. The ambiance is intimate yet lively, sophisticated yet welcoming—it’s the kind of place that makes any night feel special.
The food was phenomenal, with every dish beautifully crafted and full of flavor. The cocktails and wine selection? Absolutely top-tier—each drink perfectly balanced and complementing the meal. Sitting there, enjoying incredible food, sipping on a perfectly made cocktail, and watching the city lights come to life—it was nothing short of magical.
Cindy’s isn’t just a restaurant; it’s an experience. Whether you’re there for a romantic evening, a special occasion, or just to soak in one of the best views in Chicago, this place never disappoints. It’s truly one of my favorite spots in the city, and I can’t wait to go back! Five stars all the way! ✨🍷🌆
Sami
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March 19, 2025
Stopped here for lunch with a few friends - we didn’t have a reservation and it was a Friday so it was very busy. We just went over to the balcony/patio outside and enjoyed the views and beautiful weather, while we were waiting for our table to be ready. The space is large and very lively, great ambiance.
The menu itself isn’t very extensive - just a few options for entrees. I ordered the fish and chips and my friend got the chicken sandwich. My fish & chips were okay. It felt very greasy but the flavor overall was decent. My friend really enjoyed her chicken sandwich! Service was fine, our server was polite and checked in on us from time to time.
I wouldn’t necessarily go here again for a meal, but would love to grab a drink here and just enjoy the outdoor space!
Ashley W
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March 08, 2025
The restaurant is on the rooftop of a hotel and has both indoor and outdoor seating. This place fills up fast and reservations are definitely needed. The vibe is upscale, but chill. The menu isn't extensive, but has a good mix of options. Our server had great energy and knowledge about the menu. A friend is gluten free and allergic to citrus 😩. He explained each of the menu items, the food prep and she was able to select with confidence. The food was good, but the dessert menu could be better. Before your reservation, get there early and grab a drink at the game room on the second floor of the hotel.
Melissa Karl
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March 12, 2025
The ambiance and the view are a WOW! And the food was great! We went for lunch and was able to get there early enough to be at the rush. We ordered the Korean Fries Chicken Sandwich, and the Harvest Grain Bowl w/shrimp added. Delicious!
S LaPlante
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February 07, 2025
Loved the ambiance and food here! We had a girls trip to Chicago and this place had been on my bucket list for some time. We came Sunday morning at 10 am and got prime seats at the bar for breakfast. Only a handful of other people had arrived and no one else was yet at the bar, we were relieved.
Our bartender was very attentive and welcoming. Our food was nothing short of amazing, but I will say a bit pricey. My avocado and toast was $27 with the addition of the egg. We ordered mimosas, and it was a nice size serving.
Will return and recommend!
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12 S Michigan Ave, Chicago, IL 60603, USA
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I’ve been to Cindy’s Rooftop multiple times, and it never fails to amaze me—but the most unforgettable visit was when I went with my girlfriend for one of the best and most romantic dinners we’ve ever had. Everything about this place is pure magic. The unobstructed view of The Bean, the water, and the Chicago skyline creates an absolutely breathtaking backdrop, especially at sunset when the city is glowing. The ambiance is intimate yet lively, sophisticated yet welcoming—it’s the kind of place that makes any night feel special. The food was phenomenal, with every dish beautifully crafted and full of flavor. The cocktails and wine selection? Absolutely top-tier—each drink perfectly balanced and complementing the meal. Sitting there, enjoying incredible food, sipping on a perfectly made cocktail, and watching the city lights come to life—it was nothing short of magical. Cindy’s isn’t just a restaurant; it’s an experience. Whether you’re there for a romantic evening, a special occasion, or just to soak in one of the best views in Chicago, this place never disappoints. It’s truly one of my favorite spots in the city, and I can’t wait to go back! Five stars all the way! ✨🍷🌆
Stopped here for lunch with a few friends - we didn’t have a reservation and it was a Friday so it was very busy. We just went over to the balcony/patio outside and enjoyed the views and beautiful weather, while we were waiting for our table to be ready. The space is large and very lively, great ambiance. The menu itself isn’t very extensive - just a few options for entrees. I ordered the fish and chips and my friend got the chicken sandwich. My fish & chips were okay. It felt very greasy but the flavor overall was decent. My friend really enjoyed her chicken sandwich! Service was fine, our server was polite and checked in on us from time to time. I wouldn’t necessarily go here again for a meal, but would love to grab a drink here and just enjoy the outdoor space!
The restaurant is on the rooftop of a hotel and has both indoor and outdoor seating. This place fills up fast and reservations are definitely needed. The vibe is upscale, but chill. The menu isn't extensive, but has a good mix of options. Our server had great energy and knowledge about the menu. A friend is gluten free and allergic to citrus 😩. He explained each of the menu items, the food prep and she was able to select with confidence. The food was good, but the dessert menu could be better. Before your reservation, get there early and grab a drink at the game room on the second floor of the hotel.
The ambiance and the view are a WOW! And the food was great! We went for lunch and was able to get there early enough to be at the rush. We ordered the Korean Fries Chicken Sandwich, and the Harvest Grain Bowl w/shrimp added. Delicious!
Loved the ambiance and food here! We had a girls trip to Chicago and this place had been on my bucket list for some time. We came Sunday morning at 10 am and got prime seats at the bar for breakfast. Only a handful of other people had arrived and no one else was yet at the bar, we were relieved. Our bartender was very attentive and welcoming. Our food was nothing short of amazing, but I will say a bit pricey. My avocado and toast was $27 with the addition of the egg. We ordered mimosas, and it was a nice size serving. Will return and recommend!