5-Star Escape to the Skyline: Cindy's Rooftop Delivers on Cocktails and Chicago Magic Nestled on the 13th floor of the Chicago Athletic Association Hotel, right across from Millennium Park, Cindy's Rooftop is the kind of spot that turns an ordinary evening into a postcard-perfect memory. I visited on a crisp September sunset, prime time for that golden-hour glow and it didn't disappoint. This isn't just a rooftop bar; it's a front-row seat to Chicago's soul, where the cocktails steal the show and the views make you forget the world below. Let's start with the star: the panorama. Step out onto the terrace and you're hit with a sweeping vista of Millennium Park's Cloud Gate (aka The Bean) shimmering in the light, the endless blues of Lake Michigan stretching to the horizon, and the jagged Chicago skyline piercing the dusk. It's the best view in the city, no contest. Whether you're watching joggers weave through Grant Park or the distant lights flicker on as night falls, it's mesmerizing. The glass atrium keeps the wind at bay while letting in every ray of that famous Windy City sun, and those outdoor fire pits add a cozy glow for cooler evenings. Pro tip: Go early to snag prime patio real estate; it's buzzing with locals and tourists alike, but the energy feels electric, not overwhelming. Now, the cocktails oh, where to begin? Cindy's boasts one of Chicago's top programs, and it shows in every meticulously crafted sip. I kicked off with the Grey Garden, a herbaceous gin-based elixir with floral notes that cuts through the skyline haze like a dream. It was balanced perfection: bright, boozy, and begging for a second round. My girl opted for the Re-Animator, a bold rye whiskey number with spicy undertones and a citrus twist that evoked autumn leaves in a glass. And we couldn't resist the classic Old Fashioned smoky, not too sweet, with just enough orange peel to tie it all together. These aren't watered-down hotel pours; they're thoughtful, seasonal "potions" (as the menu charmingly calls them) that highlight local spirits and fresh botanicals. Prices hover around $18-20, which feels fair for the quality and the vibe. Pair one with the sunset, and it's worth every penny. Service was swift and knowledgeable, even amid the happy-hour hum, guiding us through the menu with insider tips on the best sips for view-gazing. If you're in Chicago chasing that quintessential rooftop romance or just need a break from the Loop's hustle, Cindy's is your spot. It's pricey and popular but for cocktails that rival any speakeasy and views that rival a private jet, it's an absolute must. Five stars! Cheers to Chicago's crown jewel! read more

OMG! We dined at Cindy's Rooftop for a team dinner. I was impressed from the moment I walked off the elevator to the time I left. The service was excellent. The hostess, server, and food runners were all very nice. The location was very industrial and just plain cool. Have me loft living in a big city. The rooftop deck is the show stopper. The views are night left me loving Chicago. I would absolutely for sure come back here next time I'm in town. read more

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We went here for a few drinks at the bar and some snacks (without reservation). Such a beautiful, vibrant spot with a gorgeous view of the Millennium Park. Drinks and service were great. Food was decent but not so memorable. Overall, we had a good time. It's such a popular spot that you should get a reservation way in advance if you plan to get a full meal here. read more

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Had a lovely birthday dinner here. The rooftop boasts stunning views of Millennium Park. The food was surprisingly exceptional. They had an exquisite handmade lamb bolognese gnocchi as a special. It was decadent and each bite was heavenly. The Burrata appetizer ($21) and Short Rib ($46) were also outstanding - the short rib portion was enormous - definitely split this! To top off the meal was a delicious, rich pot de crème with a "Happy Birthday" chocolate piece and a candle. The interior is elegant and the staff are attentive and courteous. read more

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First night we went we had only wanted to get dessert and the hostess's were being pretty rude about it and said we could order to go at the bar but when we walked inside to try to order I had made a mention of it to a man working inside and he got us a table for dessert no problem. The dessert and drinks were really good and we had gone the next mornin for brunch and those pancakes were soooo good! Carrot cake pancakes. The view from our table was also very nice. Very cool place to go for brunch but I would avoid dinner they seem more rude. read more

Cindy's Rooftop - New American Near Me - Chicago, Illinois

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Cindy's Rooftop is a great place to visit while you're in Chicago- it offers panoramic views of the city and overlooks millennium park. Definitely worth visiting for brunch, lunch, or dinner and drinks. The only downside was that the drinks didn't really taste like there was alcohol in them. Other than that would definitely recommend visiting. read more

Cindy's Rooftop - New American Near Me - Chicago, Illinois

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Went for some after dinner cocktails. Was a good view of the bean, lake and pretty good drinks. read more

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For the number of times I have been here, I have no idea why I have not written a review for this joint. The Doctor and I have been here multiple times and simply love the view. Full disclosure, I have never been here at night as I do not want to do with the crowds. We usually try to come here when we know we can get a table on the balcony and watch the view of the city, which is amazing. In full disclosure, the food is not what gets me into Cindy's. Don't get me wrong, the food is good and I love it. But if I never eat there, I would still love coming here to have drinks, chat with The Doctor and take in that view of the city. The wine list is solid for sure when it comes to sparkling. I don't do reds or still wines for the most part, so I can't speak to those, But the sparkling and champagnes on the menu are very good. Prices are decent for what is being served downtown. Cocktails (per The Queen) were delish, but be warned that they are about $18 each. My recommendation is to get a reservation on a nice day, get drinks and have a good time chatting and chat that view. read more

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Great location with nice view when you step out on the viewing balcony. Arrived between lunch and dinner so they were only serving lite bites. Had the smoked whitefish dip. It was ok. Service was good. Cute little place, would like to try it for lunch or dinner next time. read more

Cindy's Rooftop - New American Near Me - Chicago, Illinois

I've heard mixed reviews about Cindy's Rooftop but wanted to give it a shot during restaurant week and I'm so glad we did! We snagged a reservation for weekday during lunchtime (reservations open up 2 weeks in advance) but felt like we didn't need to since we came early. It started filling up around 12/12:30 PM. It was freezing the day we came so the patio was closed since it was icy outside which was a bummer. We were seated by the fireplace which was nice and cozy but part of me wished we were seated closer to the windows so we could peer out over Millennium Park. The entire party must participate in restaurant week so needless to say, hubby and I both chose courses from restaurant week. We shared the whipped ricotta which was surprisingly addicting. There was plenty of whipped ricotta so we asked for more bread to go with it. I could have walked away at that point and stopped eating since I was getting full off of the whipped ricotta with sourdough. I had the lamb shawarma (basmati rice, tabouli, feta, tomato, pickled red onion, hummus) while hubby had the short rib melt (dijon, gruyere, sourdough, frisee salad). We both enjoyed our dishes and I was secretly glad I didn't get the short rib melt since I couldn't consume anymore bread at that point. All of the ingredients in the lamb shawarma bowl were fresh and delicious. I couldn't help but to keep eating despite being so full. I eventually made a conscious effort to push it aside so I could make room for dessert which was a delightful chocolate mousse cake. I must have inhaled the cocoa powder because I coughed up a storm after I started eating it. I couldn't help but feel the glares from other diners around me but the cake was too good for me to resist eating. Service was good and my water was constantly refilled. However, the pace our food came out was on the slower side. Our waiter was kind enough to find a spot for us to take photos inside and took a bunch for us in pro fashion. Overall, we had a good time and would love to come back during the summer to enjoy the patio. read more

Atmosphere is amazing, the place is very open with lots of natural sunlight. The patio has a good amount of space with a gorgeous view of the city and lake. We came here just for drinks. They have a large selection of wines, beers, and cocktails. The price is what you expect for this type of bar/restaurants. We got 4 glasses of wine total and the bill was 100 dollars with tip. Service was kind. Nothing too special. Long wait to actually get up to the bar. Overall, it is worth to visit this spot to get a drink and show friends who are visiting from out of town. read more

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Cindy's rooftop and a beautiful sunset is probably the best combination for a summer dinner! read more

Cindy's Rooftop - Strawberry Mille Feuille** - New American Near Me - Chicago, Illinois

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A trip to Chicago is not complete without visiting Cindy's Rooftop. The ambiance is lively, with a wonderful view of Millennium Park and The Bean. It can get very busy, however you can still walk in without reservation. Bar seating is on a first come, first serve. You can order your drinks at the bar and take it with outside and enjoy the view. The drinks are crafted well, the menu offers elevated comfort food. The service is exceptional. read more

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We stopped at Cindy's rooftop for a late night dessert and drink. The best part of the experience was going outside to the outdoor area and look over Chicago at night. On a beautiful summer night, this was a spectacular experience. The booth and chair we sat in were very worn out and not very comfortable. The service was good and we ordered the pecan chocolate cake dessert. Dessert was actually pretty good and large enough for two to split. read more

Cindy's Rooftop - Pecan Chocolate Cake - New American Near Me - Chicago, Illinois

OMG! Where do I start?!! The view is amazing and we scored a table outside at the railing with a magnificent view of Millenium Park and Lake Michigan. The food is superb...Barley Salad with the best salmon! The wait staff, especially Johan, were super nice and accommodating (but really.. all the staff) If I lived in Chicago, this would be my place. read more

Cindy's Rooftop - View from our table - New American Near Me - Chicago, Illinois

This is one of my favorite restaurants in Chicago. Loved the food, service and view! Highly recommend!

This place is stunning, with modern, large glass windows that open up to a fantastic view of Chicago! A lot of Yelpers say that the wait is worth it due to the view and vibes. Luckily for my friend and me, we sat down right away and arrived when they just opened. Fifteen minutes go by, and this place is popping and filling up just as expected. I recommend coming for the views and getting drinks at their outside bar because their food was just okay for us. My buddy enjoyed his Korean Fried Sandwich, but the fries and Chef's Salad could have been better. I got the job done, but I can tell they are not known for their food. The service here is unbeatable, though, and was probably the best service I've had at a restaurant for all of 2024. One gulp of my water, and the waiter was on his way to fill it up. They filled up my glass about every 10 minutes, and I loved it. read more

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The food was pretty decent, but def paying $$$$ for the view and ambiance. The fries here are my ideal fries- not oily at all, but still crispy and crunchy! Same went for burger- not oily at all and did not feel bad after. The lamb shawarma bowl was also surprisingly filling and no complaints about flavor. Portions are decent size. We were able to walk in on a Thursday afternoon, albeit seated on the silver area and not the actual tables but no complaints! We were also hotel guests and that did not help with anything from our experience. Recommend reservations if you want to get seated asap. Fun touristy spot and great view read more

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Best food!! Great bar staff. Can get crowded but the crowd was worth the excellent meal and drinks....did I mention the view? Its amazing!

Food tasted good but halfway though the meal my friend had an allergic reaction. She is allergic to eggs and asked several times to see if eggs were in the meals she was interested in and emphasized that she had an allergy so that they would check for cross contamination. She started feeling very sick and immediately had to leave. We asked for the check because of her reaction and not only did they do NOTHING for us, they took nearly 10 minutes to bring out the check. I waited by the table standing for the check and they seemed in no hurry after being notified she was having an allergic reaction. The check was not comped whatsoever, her meal that was contaminated was full price, no apology, nothing. Unprofessional and no empathy for the situation we were in. Lucky she is okay now but no thanks to them! read more

Came to Chicago for my birthday trip! Literally writing this as I leave the table! Michelle our waitress was wonderful! scallops 8/10 Truffle fries- 9.3/10 the black garlic aioli honestly makes it a 10. We each got one of the seasonal drinks! Very good! Very potent!! The vibe of this place is also very good!! You can do a date night or like a girls night out! Def recommend! Pretty pricey, worth it read more

Cindy's Rooftop - Truffle fries - New American Near Me - Chicago, Illinois

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The ambiance and service are exceptional. Food quality is top as well. They dishes are completely overpriced given the portion sizes. I would go here for drinks rather than dinner. read more

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Loveeeeed this place. Went post marathon. Food was great an awesome drinks !!! Can see all of Chicago! read more

Cindy's Rooftop - New American Near Me - Chicago, Illinois

First time at Cindy's and the view from the roof is great. Very very busy, so if you're looking to enjoy lunch I would book a week or two in advance! I got lucky since I was dining alone and got a last minute reservation. If I would've known you could just go to the rooftop and have a drink without sitting for lunch I would've definitely done that, the food was super pricey, I'd say you're paying for popularity. read more

Cindy's Rooftop - New American Near Me - Chicago, Illinois

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Also had the slow cooked baby back ribs. Had high hopes but was disappointed. Found it dry and without much taste. We got the side of sautéed vegetables which was buttery good. Would pass on the baby back ribs and try something else. Vegetables were good tho. read more

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Cindy's Rooftop is that effortlessly cool friend who's gorgeous, funny, and somehow makes a curried shrimp dish taste like a religious experience. The salmon tartare? Silky, bright, borderline smug with how perfect it is. Toss in panoramic views and this might be one of the best spots in the city. Go for the food, stay because you've suddenly developed a rooftop personality. read more

Cindy's Rooftop - New American Near Me - Chicago, Illinois

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Deviled eggs are so good. Need to book a reservation if you don't want to wait. Elevator up has a line but worth it. Great views off the rooftop. read more

Cindy's Rooftop - Menus - New American Near Me - Chicago, Illinois

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We visited Cindy's Rooftop for the stunning views of Millennium Park and, of course, the famous Bean! Although we couldn't get reservations, we were seated quickly as walk-ins on a Saturday. Initially, we were placed at the counter, but once a table opened up, we were able to move. Many guests come for the drinks and the scenery. I was hoping for a bigger food menu on the weekend, but it was limited to brunch options only. We ordered the Beau Soleil oysters, classic breakfast, Aphra-Cadabra, and Pink Panthers. The dishes were nicely presented, though the portion sizes felt a bit small given the price. We enjoyed our experience, but the brunch cost was on the higher side - about $150 for two people. The atmosphere can be quite noisy as well. Nevertheless, the rooftop location is gorgeous, making it a wonderful spot for dining. I recommend securing a reservation! read more

Cindy's Rooftop - Pink Panthers, Classic Breakfast, Aphra-Cadabra, Beau Soleil Oysters - New American Near Me - Chicago, Illinois

Suchhh yummy cocktails. We went for a nightcap after dinner and these drinks were the perfect end to our night. The service was good - our bartender answered all our questions (: read more

Cindy's Rooftop - One Moment in Thyme (L) & Warm Embrace (R) - New American Near Me - Chicago, Illinois

Took some of my family here who were visiting from out of town. We went for an early happy hour on a Friday and the entire staff was so lovely! The drinks are pricey, but very creative and delicious. Unfortunately, it was a cloudy day. However, the view from the balcony is wonderful. My family loved seeing the city and lake views and definitely decided that we will be back for another visit. read more

Our food was a bit hit and miss. The acorn squash appetizer and mushroom risotto were both tasty. Surprisingly the broccolini (which should be the easiest) was not great. It was tough and under seasoned. It was a bit of a chaotic atmosphere with people sat really close to us, and people constantly walking close to our table. The view was nice on balcony. read more

This place was recommended to us and overall, it was great. Upon arrival to the bldg, enter and take the 3 elevator to the R level, that's the restaurant level. Check in. Reservation is recommended. Restaurant's ambience cannot be beat. High ceiling with glass roof as if you're sitting in an atrium. At dinner you can see the sunset while enjoying your cocktail and meal. Bar is impressive. Although decent amount of chairs, it was completely filled up. You can work onto their outdoor patio and be wow by the view of the water, the Bean, the park all in front of you. The gal that checked us in seems as if she's done for the day. She just looks exhausted. Our waiter was ok as well, seems like he's ready for closing time, although it's about another 2 hours. Thank goodness the food was amazing!!! Menu was not big but the items we ordered did not disappoint. It made the night. The view was re 2nd. We were seated in the room on the side so it was a bit quieter. Overall, a nice dinner and would return. read more

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Cindy's is a special place! I try to visit every time I'm in Chicago, primarily as a nod to my mom, Cindy who passed several years ago. This visit, was even more special as it would have been her 79th birthday this year. We like to sit at the bar and have always had amazing bartenders. Huge shout out to Chris and Will. They are personable, welcoming, provide great recommendations for other restaurants and cocktail lounges. I can't say enough about the hospitality we've encountered at the bar at Cindy's. Now, for the food!! The mushroom toast was absolutely phenomenal and I can't wait for next chance to order it!! The burger and fries were great (ordered by my husband) and I had the Caesar salad, which I love the little gem lettuce! While pricey, it's worth it for the food, hospitality and atmosphere. We got married in Chicago last year and took some photos on the rooftop overlooking Lake Michigan and enjoyed reminiscing and recreating the memories again this year! read more

Cindy's Rooftop - New American Near Me - Chicago, Illinois

Cindy's was awesome!!!! The drinks were delicious and ~handcrafted~ The views from the outside terrance were unbeatable. We just stopped in for a drink, but seeing the inside and experiencing the high quality service and cocktails made me want to book a reservation to come back for dinner!!! read more

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I am a local and was staying at the hotel for a staycation. I made a reservation 2 months in advance for a Saturday brunch. I feel you are paying for the view, but that's why you eat at a rooftop bar overlooking Michigan Ave. The Service is good, food was delicious, portions ok sized. I would go back, but probably for the drinks. Drinks tasted great and were strong. The balcony is open for pictures even in the winter. See if you can spot the original Andy Warhol read more

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This was a magical experience with amazing views! It's one of the first things we did when we got to Chicago, so it was hard for anything else to rival this experience on the trip. We stayed for the sunset and although you might not see the sun go down the soft glow over the bean and the water is breathtaking. We didn't have a reservation so we added our name to the list which could've taken up to 90 minutes, but by the time we ordered a drink and looked at the view, we had a text and was seated. The food was delicious, pricey, and limited for those who don't have extended pallets, like my companion. So we just split a couple of things on the menu and planned to go out after for more extensive Tastes of Chicago. Our waiter was extremely knowledgeable and seemed to have a passion for his job! read more

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No visit to Chicago is complete without going to Cindy's Rooftop for drinks, food, and the view of the city. Located at the top of the Chicago Athletic Association (hotel), you'll be greeted by a friendly host and tended to by knowledgeable servers. The menu rotates seasonally, so some items will not be in the rotation since ingredients are sourced locally. Talking to the server about some dishes was enlightening as he knew so much about the ingredients, quantity, and flavors. I had the kurobuta pork collar and my gf had the green curry prawns. Both of these were packed with flavor and hit the spot on a slightly colder evening. You absolutely have to order some drinks, and we certainly did. I had the Kokomo, a passionfruit gin drink and it was the right balance of sweet and slightly punchy. I went on a cloudy day so I didn't get to enjoy the views of Millennium Park, but the inside of Cindy's has great atmosphere so I didn't feel like I was missing out. There's a reason why Cindy's at the top of many lists. Everything they do from front of house to back all adds up to create an experience that delights your senses. read more

We stopped in after visiting The Bean. The restaurant is sleek and stylish, with gorgeous views overlooking Lake Michigan and Millennium Park. What we ordered: * Deviled Truffle Eggs - Absolutely divine. Silky, buttery eggs with just the right hint of earthy truffle. A must-try. * Lobster Roll - Lightly dressed and tasty, with a buttery bun that hit the spot. That said, for the price point, we were hoping for a bit more lobster meat. * Cheeseburger - Juicy with a delicious char that gave it that perfect grilled flavor. read more

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I completely get why this place is on everyone's list. The view is unmatched and the vibe is amazing. The restaurant itself is so cute and I can see it being great year around. Our waiter and the others were zipping around and catering to the constant flow of people. The patio does get crowded but was never overly so. I'm glad we got a table though even if we just got one round and a snack. Espresso martinis are plentiful despite not officially being on the menu. It was a top 3 contender of my many for the weekend visit. The pulled pork sandwich we split was a bit small to split but was delicious! I kinda wish me and my husband each had our own since we were so hungry. Would love to return on another trip! read more

Cindy's Rooftop - Espresso Martini - New American Near Me - Chicago, Illinois

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The views are great, and they now take reservations on OpenTable. It's always been overpriced, but I think that has gotten out of control: as soon as we sat down, the server told us "the old plates you were used to sharing between two people -- they're smaller now and you won't be able to share." Then, they also tack on a service fee at the end. The food was worse than I remember -- the artichoke was flavorless and bland. The risotto was undercooked and lacked depth of flavor. read more