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Cindy's Rooftop — honest bar & grill in Loop. Buzzy, energetic room where the crowd adds to it. Solid drinks, with the bar pulling its weight. "Right around Golden hour the view over the balcony was phenomenal" — Ana Valle
Eric Boesen
210 reviews
“The food itself was absolutely amazing—beautifully prepared and full of flavor—and the view was just as stunning, which made the whole experience even more special”
First thing. If you plan to dine here, make sure to make a reservation.
12 S Michigan Ave, Chicago, IL 60603
“We celebrated my daughter’s 19th birthday at Cindy’s Rooftop, and it was such a lovely experience from start to finish.”
We celebrated my daughter’s 19th birthday at Cindy’s Rooftop, and it was such a lovely experience from start to finish. The staff were incredibly friendly and welcoming, which immediately set the tone for a relaxed and enjoyable evening. The ambience felt calm and inviting—perfect for a special family celebration. Of course, the views are what make Cindy’s truly unforgettable. The sweeping city skyline is beautiful on its own, but the direct view of the Bean made the night feel extra magical. It’s one thing to visit Millennium Park, but it’s another to enjoy it from above with great food, great company, and a warm atmosphere. Overall, it was the perfect spot to mark a milestone birthday. We left with full hearts, happy memories, and a new favorite place to return to.
Lavender Haze
Feb 2026
“This place is such a cute little spot with so much charm.”
This place is such a cute little spot with so much charm! From the moment we arrived, the atmosphere was welcoming and relaxing. We started off with drinks at the bar, and Johann was our bartender—he was absolutely awesome. He was friendly, engaging, and clearly passionate about what he does. Johann took the time to talk with us about the drinks, offered great recommendations, and made us feel genuinely welcome right away. Huge shout-out to him for making such an incredible first impression! After that, our server Ben was just as fantastic. He did an amazing job walking us through both the drink and food options, answering questions, and making great suggestions. You could tell he really knew the menu and cared about providing great service. The food itself was absolutely amazing—beautifully prepared and full of flavor—and the view was just as stunning, which made the whole experience even more special. Overall, everything from the service to the food to the atmosphere exceeded our expectations. It was a truly wonderful experience from start to finish. We will definitely be coming back, and congratulations to the entire staff for doing such an incredible job. You are all awesome!
Eric Boesen
Jan 2026
“Amazing views, great vibe, and a genuinely enjoyable experience from start to finish.”
Amazing views, great vibe, and a genuinely enjoyable experience from start to finish. The terrace overlooks Millennium Park and the lake, and the panorama never gets old. Everything feels thoughtfully designed—from the seating to the lighting to the way the space flows. Service is attentive without being intrusive, and the drinks are well made and refreshing. The food complements the setting perfectly—seasonal, well-executed, and tasty. It feels both elevated and relaxed at the same time. One of the best spots in the city for sunset views, casual drinks, or a special meal with a view. Highly recommend.
Axel
Dec 2025
“Loved the views from here as it offered a fresh perspective of the city.”
Loved the views from here as it offered a fresh perspective of the city. I ordered a pisco sour which was made well and enjoyed it out on the terrace overlooking Millennium Park, the Bean and the lake.
Christine Kim
Nov 2025
“Had to visit from a recommendation and so happy I did.”
Had to visit from a recommendation and so happy I did. Beautiful view, hip cocktails list, will visit amd try the food next time
Sifu Stephane Patenaude
Nov 2025
“stunning view and Ashley at the bar was so helpful places to see and go (i’m from dallas).”
stunning view and Ashley at the bar was so helpful places to see and go (i’m from dallas). She was amazing and had great recommendations! Had the shrimp roll and it did not disappoint!
Sydney Beck
Nov 2025
“What a great spot.”
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.
Seamus McEvoy
Nov 2025
“First timer and gotta say: what a pleasant experience 🥹 Super friendly bartenders (s/o to Chris...”
First timer and gotta say: what a pleasant experience 🥹 Super friendly bartenders (s/o to Chris for taking care of me!) and couldn’t have asked for a better to spend a lovely Chicago fall afternoon in the city + celebrating another trip around the sun hahaha a cute time was almost certainly had. The fire pits they have outside in the rooftop = A1. Whether you’re a local or visiting, def make sure to stop by :)
Daisy Magana
Oct 2025
“Came here with a friend when I was staying at the hotel.”
Came here with a friend when I was staying at the hotel. I was very impressed! The drinks were all unique, not your usual classics but very well made. The truffle fries were delicious and massive. The kale salad was also great! Right around Golden hour the view over the balcony was phenomenal. This is such a great place!
Ana Valle
Oct 2025
“Yes!!! It was so NICE and will be a definite repeat. DELISH Food and drinks. Great service! I have...”
Yes!!! It was so NICE and will be a definite repeat. DELISH Food and drinks. Great service! I have to say, this bartender was 💯‼️#Jenesis❤️ She is such a vibe and made our beverages to perfection👌🏾🥃
Jaymara Baker
Oct 2025
“The rooftop in Chicago is definitely a place worth visiting.”
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
Salvador Torró
Oct 2025
“Fun rooftop bar with creative and well-balanced cocktails and awesome views of downtown, Lake...”
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!
Roger Hopper
Oct 2025
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