Rooftops are my favorite and so is Cindy's Rooftop! The view is spectacular and so is the food and the restaurant. I had the braised short rib, the Kokomo and the beet which did not disappoint. Our server Anthony was very helpful with the recommendations. This is a must try when visiting the Chicago area. read more

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

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Food is pretty good, prices a bit high but to be expected. Cocktails were a bit hit or miss. Service was excellent, and the view was worth the trip by itself, especially at night. read more

We went here for drinks and their Parmesan truffle fries were phenomenal. I tried a CBD mocktail for the first time and it was delicious. Would definitely recommend for casual drinks, rooftop photos, and good service. read more

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

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When planning a visit, it's advisable to reserve a table in advance, esp for brunch, as there tends to be a waiting list. I reserved 2 weeks in advance for party of 5. The brunch experience was enjoyable & straightforward, though the service was somewhat disorganized. We waited for our waitress to attend to us, likely due to the hectic hour. It's worth noting that the prices are on the higher side for brunch menus, but it's Chicago, on a rooftop with views of The Cloud Gate, so all adds to the overall experience! read more

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What an awesome rooftop bar to enjoy the views of Millennium Park! We joined a friend here and ended up staying for dinner. On a Sunday evening we actually visited the rooftop at noon to be able to make a reservation as it was difficult to call or book one online, but they were able to accommodate us well. We ordered a few n/an and alcoholic drinks, appetizers, and main courses. Due to the side of the kitchen the server told us they would need to take our food order in entirety (appetizers and main course ) Drinks: DELICIOUS! Very please with my n/a drink, and my husbands was good too. Almost made me question if there was alcohol in it! Food: good but a little over priced for what it was. We ordered buns, deviled eggs, and artichoke- all of which came with interesting sauces but weren't anything spectacular. Main Course: my husband ordered a Cesar Salad which he said was good - a classic salad. Our friend ordered mushroom risotto- she also said it was good but she'd hoped to have a few more mushrooms in it. And I ordered the Long Salmon, which was also good with a green sauce but again, a little over priced for what it was. There were a couple of conferences in the area so the restaurant was a bit packed with those events but we snuck out to the rooftop (even though it was closed with a private event) to grab a photo real quick. Overall, awesome spot with great views and cocktails. Food was delicious but as mentioned we probably won't eat there again purely due to the price point but otherwise had a wonderful time! read more

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Came for lunch with a friend and we ordered a smash burger and a monte cristo. The smash burger was good- the caramelized onions were a nice touch. The monte cristo's bread was a little soggy for my taste, but the sweet and savory flavors worked together well. The space was open, light, and airy, with lots of natural light from the big windows and glass ceiling. The patio has a view of the Bean and the Chicago skyline, which was nice to experience after we finished our meal. Our server was very kind and despite seeming a little frazzled because he presumably was serving many tables, he always made sure we were accommodated. read more

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

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Big fan - especially to come to for an occasion. We came here for brunch and got two classic breakfasts, a coffee , a croissant, and one mixed drink. Total cost was about $100. If that sounds like a lot - yes it is - but this is an experience place. You can't beat the rooftop view and the place is special. I really liked that they labeled their menu gf for those celiacs like me who eat gluten free. Again - the food did not blow me away but the place did. It was great and the people were too. It is best to have a reservation so you don't wait an hour. read more

When planning our trip to Chicago, a couple of friends of mine mentioned that this was a really nice spot to visit. My friends and I decided we wanted to have lunch after our boat tour at this location. We found parking in a building, not far and walked over. We somehow hit the perfect time as we did not have a reservation, but we're still able to go directly upstairs and put our name down on the list. By the time we walked over to the bar and ordered our table was ready which was awesome. The view in this place is amazing being able to see millennium Parkclearly and the water. It definitely makes for a nice ambience. It was still brunch time so we ordered a few things off the menu. The pumpkin cheese cake monkey bread was amazing to start. I thought that it might be too sweet, but it was definitely not. It had a nice balance. For my main, I did the smash burger. I love a Smashburger as they were thin and cooked well which is my preference. My friend tried the French toast, which they also enjoyed. It was a little rich, but it was to be expected. Our cucumber drinks said they would be a little spicy, but they weren't but they were still really good. Love this place I would definitely recommend to any of my friends were visiting Chicago. read more

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Steak was PHENOMENAL !!!!! Our server Michael was so helpful and quick! Also the view is unbeatable :) read more

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

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I would be hard pressed to think of a stronger five-star dinner experience. We went after work on a Wednesday, thinking of drinks and an appetizer and expecting to wait a half hour to 45 minutes with no reservations.. We got a drink and proceeded to the packed terrace space. The old fashioneds were well made and well balanced, owing to a fine aged bourbon. Probably 10 minutes later, we got a table. We ended up splitting an appetizer (Get the lobster and crab! Life is short!) And then we split two entrees over the course of a leisurely and completely relaxed dinner. We didn't expect great food, but everything kept just being wonderful. The prawns in chorizo green curry and sweet corn campanelle were both complex and delicious. We were tempted to lick the plates. The service was outstanding, friendly but super professional and attentive to detail. Despite being a busy and popular place, we didn't feel even a little rushed. Beautiful ambiance on a late summer evening. This place really shines during golden hour. Check your weather app and plan accordingly! read more

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Perfect spot to pop in, grab a drink, & enjoy a view! Absolutely love this spot and highly recommend Cindy's Rooftop. read more

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Gorgeous view of the Chicago downtown from this building. Located at the top of a nice hotel with large amounts of space. The decor gives vintage Gatsby elegance but the ambiance of customers is casual. My friend ordered his favorite whiskey neat and that was the best thing of the evening. We paid $32 for a cheese board full of our favorite spicy meats and veggie items. Sad to say, none of the delicacies were spicy or close to. The berry preserve was very sweet and paired well with the horseradish but some of the prosciutto had too much fat on it - felt like I was chewing forever. To have spent over $50 for a cocktail and cheese board is wild to me. I'd love to try Cindy's again on a brunch day. read more

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

This is a fairly popular rooftop bar/restaurant in the heart of Chicago Loop, right next to the bean. I scored last minute reservations for Labor Day for a date-night occasion, and it was perfect to start off with some drinks over the outdoor terrace, followed by a fancy dinner after. There was about a 15 minute wait past our reservation time, which was more than okay since we could chill in the terrace and soak up the views of the city. Afterwards, we were sat at a table. My complaint is that the tables are distanced really closely, so there is a possibility you could hear other people's conversations around you and vice versa. We got the charcuterie board which is good but pricey, with some of the fixings that are commonly seen in the board like prosciutto and cheese, as well as almonds, honey, and pickled vegetables. I am not a fan of pickled vegetables and olives, but they did it decently. We also got the green curry prawns that were giant and super fresh. There were 6 of them, accompanied by some bread. I wished there was more sauce, but it was nicely spiced and super flavorful. For drinks we got Downtown Train and Peachy Keen, which is gin-based and whiskey-based, respectively, and both are fairly strong. The cocktails have decent presentation, mostly from garnish, and $18 each so it is a bit pricier but you somewhat pay the premium for a rooftop. Service is okay. I guess they course the dishes so we thought we waited a long time for the green curry prawns, but they mostly want to clear the charcuterie first. Water refills were apparent. I overall do enjoy the ambience here but would go again just for the drinks and the terrace, as the food is good but a bit pricey for what you get. read more

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View great. Food great. Reservation process is ridiculous. But I complied and scored a 2pm lunch reservation on my Birthday! Reservation asked if we were celebrating anything and I said a birthday. We arrived at 5 minutes to 2pm. Made to wait until 2pm. No one else waiting. Okay hostess stand. We see you. Then sat at a 6 top. There were several two tops so they agreed to move us. The main issue was the waiter then told us they stop serving at 2pm so we needed to get our order in asap. Ordered two drinks and two appetizers and asked for a minute. He came back with drinks and said we had to order. So we did. Allll the food came at once. Two apps, two meals and no room on the small table. Eventually we took the oysters shells off the dish and placed them on our plates. So food was good. View amazing. Restaurant pretty BUT we were in the elevator on the way out at 2:42pm. Absolutely criminal for a $145 lunch. If you don't want to service a 2pm resie then don't take them. And no one mentioned my Birthday which is fine, but again why ask. So we won't go back, but it is a. I've experience if you don't book the 2om and are permitted to enjoy your food. read more

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The restaurant is lovely and even has a balcony looking over the park, lake and downtown Chicago. You can expect everything to be quite pricey here. The service, while professional, was exceptionally slow. Slow enough that it took 20 mins for us to receive our glasses of wine that we ordered. The host had also mentioned to us that we only had a limited amount of time before the table was reserved for someone else and we were a bit angsty about that throughout our time here. As for the food, the half chicken was cooked very well and came with some tasty veggies. In the future, I may come back but likely only for a drink to take advantage of the view of Chicago they offer. read more

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

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We visited Cindy's Rooftop over St. Patrick's Day weekend -- one of the busiest times in Chicago -- so reservations were filling up fast. Thankfully, we got lucky! We were hungry earlier than expected, and the staff was super accommodating, seating us about an hour before our original reservation. Huge win! The vibe up there is unbeatable -- amazing city views, lively but still relaxed, and just the right amount of energy for a weekend outing. We kicked things off with dirty martinis (perfection) and shared a bunch of small plates -- oysters, burrata, and their mushrooms. Every single dish was fresh, flavorful, and beautifully presented. It was one of those meals where you want to order everything on the menu. Cindy's is definitely a must-visit if you're in Chicago -- especially for a special weekend. Great food, killer cocktails, and one of the best rooftop views in the city. read more

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

We went for my birthday a few weeks ago and I had a wonderful time! We got there early and enjoyed cocktails and nice views outside by the fire. The service was good, the cocktails were wonderful, and the food was delicious. The No Soup For You cocktail was not too sweet, and exactly as described. We had the fall squash malfadine, short rib, and baked potato. The pasta was our favorite, but the short rib was really good too. They brought a nice dessert as well. I'd happily celebrate my birthday here every year. read more

Cindy's Rooftop - Malfadine, baked potato, and braised short rib - New American Near Me - Chicago, Illinois

The drinks were creative and on point for fall. The food was great! The kale Caesar salad and the heritage brick chicken were the highlight. Love how the menu changes every season. The staff were very friendly and the recommendations were great. The terrace is open for all, and a lovely spot to take the in the views. We got to see the Christmas tree from up there. Would definitely go back. read more

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We had a reservation so we had a table. While the menu is small you can find something. Drink we're good. It was a lovely place. They also have a balcony that you can hang out on overlooking the bean. Service was friendly and the food came out quick. We enjoyed what we ordered and some items were enough to share. read more

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While in town for a convention, I had two dinners at Cindy's. The food was excellent but the service is what I'll remember. Friendly but unobtrusive. Knowledgeable and professional. A special shout out to Collette, Ennis and Will who took such good care of our group. read more

Cindy's Rooftop is the single most beautiful dining experience in Chicago, full stop. Perched on top of the Chicago Athletic Association like a glass jewel box overlooking Millennium Park, it's the place that makes you fall in love with this city all over again, every single time. You step off the elevator and your jaw actually drops: soaring atrium ceiling with twinkling lights, panoramic views of the Bean, the lake, and the skyline glittering in every direction, and that open-air terrace (when weather allows) that feels like you're floating above the world. Day or night, rain or shine, it's pure magic. Sunsets here should come with a warning label. The vibe is effortlessly cool without ever being stuffy. Brunch turns into golden-hour cocktails, which turns into late-night dancing under the stars. The crowd is a perfect mix: locals celebrating birthdays, tourists wide-eyed and taking selfies, couples on first dates, and old friends reuniting like it's New Year's Eve. The food is way better than any rooftop "has to be." The rotisserie chicken with smoky jus and crispy potatoes is legendary, the Great Lakes walleye with brown-butter vinaigrette is refined Midwest perfection, and the burger with bacon jam is one of the best in the city (fight me). Brunch is next-level: crab benedict on fresh-baked English muffins, lemon-ricotta pancakes with blueberry compote that people dream about, and those hash browns that are basically potato candy. Cocktails are stunning. The seasonal rotations are creative and balanced (the current smoked cinnamon old fashioned is dangerous), and the spirits list is one of the deepest in Chicago (rare amari, small-batch mezcals, and a non-alcoholic program that actually tastes good). The wine list is smart, and the frozen frosé or Cindy's Punch by the pitcher is basically summer in a glass. Service is warm, polished, and genuinely proud to show off this view and this menu. They'll let you linger for hours without rushing you out, even when the place is packed. Whether it's a sunny brunch with your crew, golden hour with someone special, or late-night under the heat lamps with the skyline sparkling, Cindy's makes every moment feel like the top of a movie. It's expensive, yes, but you're paying for the best seat in the entire Midwest. Cindy's isn't just a rooftop bar or restaurant. It's a Chicago rite of passage. I've brought friends from out of town here and watched their faces light up like kids on Christmas morning. I've celebrated birthdays, engagements, and random Tuesdays here. Every single time, I leave happier than when I arrived. Do whatever it takes to get a reservation (or walk in and pray at off-hours). Just get here. You'll thank me when you're sipping something beautiful with the entire city sparkling below you. Forever my favorite place in Chicago. See you at sunset. read more

One of our favorite places for brunch in Chicago! A smaller menu but something for everyone. Even if you don't get seated outside, request a table by the windows and you'll still have amazing views. read more

This place has some of the best views in the city. The outdoor patio provides a panoramic view of the Lake, Michigan Ave, and Millennium Park. The ambiance is also great, lots of beautiful people enjoying life and laughing with friends and family. Food was also good, but the star of the show is definitely the views and vibes. I'd suggest coming here for drinks and then hitting one of the steakhouses the city has to offer. I'll be back soon. read more

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We had the best time at Cindy's! We started with a Bloody Mary and Cindy's Old Fashioned. Both drinks were great, but fair warning--the Old Fashioned was VERY strong. If it wasn't 10:45 a.m., I would have been thrilled For food, my boyfriend ordered the biscuits and gravy, which he rated an 8/10. The biscuits were fluffy, and the gravy was amazing, although it did have a different texture than we're used to. Regardless, it was absolutely delicious. I opted for the quiche, and let me tell you--it was heavenly. I didn't leave a single bite on the plate! Since the Old Fashioned was a bit too strong for me, my boyfriend finished it off, and I switched to the "Trouble Will Find Me" cocktail. Wow. I could have had five of these! Amazing flavor and just the right amount of alcohol. Yes, Cindy's is on the expensive side, but it's worth every penny. The stunning view of the park and the Chicago skyline made the experience even more memorable. As an expat of Chicago, Cindy's was the perfect place to introduce my boyfriend to the city for the first time. We'll definitely be back! read more

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Cindy's Rooftop is hands down one of the most spectacular dining experiences in Chicago! Located on the 13th floor of the Chicago Athletic Association Hotel on Michigan Avenue, this place offers panoramic views that will absolutely take your breath away. Let me start with what everyone comes here for--the view is simply magical. From the glass atrium and outdoor terrace, you get stunning vistas of Millennium Park, Lake Michigan, and the entire Chicago skyline. We had a window table and could see the Bean from above, which made for incredible photo opportunities. The sunset views with the city lights starting to sparkle are especially gorgeous and create such a romantic atmosphere. The space itself is beautifully designed with an airy, sophisticated vibe. The glass atrium means you can enjoy those incredible views year-round, and they even have fire pits on the outdoor terrace in winter. The atmosphere strikes the perfect balance--refined but welcoming, lively without being overwhelming. Whether you're celebrating something special or just treating yourself to a memorable evening, this place delivers. Our server was absolutely wonderful--attentive, friendly, and made us feel like VIP guests. The entire staff clearly takes pride in providing top-notch service. They were knowledgeable about the menu and made excellent recommendations without being pushy. The mushroom risotto was outstanding--rich, flavorful, and beautifully presented. We also tried the garlic bread (honestly the best we've ever had!), and the baby back ribs which were more than generous portions and delicious. The cocktails are expertly crafted--my Old Fashioned was excellent, and they have an impressive wine selection. Yes, it's pricey, but the quality matches the cost, and you're paying for the complete experience. Make a reservation through OpenTable if you want to guarantee a table (they book up quickly, especially on weekends) Arrive early if you're doing walk-in for the best chance at window seating Consider coming for sunset--the timing is perfect The brunch menu is also supposed to be excellent (adding that to our must-try list!) If you can't get a dinner reservation, grabbing cocktails at the bar is still absolutely worth it Cindy's Rooftop is a Chicago institution for good reason. It's perfect for special occasions, impressing out-of-town guests, date nights, or simply treating yourself to one of the best views in the city. The combination of breathtaking scenery, delicious food, creative cocktails, and impeccable service makes this a can't-miss destination. We're already planning our return visit! read more

We came here for lunch, and started with espresso martinis- which were very good. For food, we ordered the fish fry and the Korean fried chicken sandwich, which both were seasoned well and good. My only complaint was that I wanted the batter on the fish fry to be more crispy- but that's a minuscule complaint. The staff members were friendly and the restaurant had a gorgeous view. It would be even prettier as the warm weather rolls in. Overall, the price was worth it for 4 drinks and 2 entrees when you consider the rooftop location and it being Chicago read more

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

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Amazing experience! The food was absolutely delicious, beautifully presented, and full of flavor. The staff was attentive and made us feel welcome from the moment we walked in. Great atmosphere for both casual dinners and special occasions. Highly recommend if you're in Chicago! read more

Came for a Sunday morning brunch -being tourists in our own city. Had a reservation for when they opened and they seated us quickly. Started with the donut which was peach cobbler and the hummingbird coffee cake. Both were delicious. We tried the avocado toast and chicken and waffles. Both delicious and didn't disappoint. Service is spectacular and the views and ambiance are top notch. read more

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When i arrived they did not have any reservations but we added our name to the list and got a table in 5 to 10 minutes. The t Drinks were refreshing but not spicy even though the name suggested it would be. The pumpkin bread was soft,warm and delicious. The pumpkin French toast was delicious and the candied walnut added a good crunch. Also had great views of downtown from the rooftop. I would recommend you check this place out if you are in town. read more

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super great environment and staff. food was good and good portions. short menu. good drinks. beautiful view. it's technically enclosed so u can enjoy all year read more

Only came here for drinks & view on the rooftop, and that was great! We tried getting a brunch res during our Chicago trip, but never managed to snag one. I was about to give up on visiting, despite all the recommendations from friends, but luckily saw last minute that you don't need a res and instead can just order at the bar and enjoy your drink at the outdoor roof space. We were wandering near The Bean on a super hot August Sunday, so we were relieved to be able to go to the bar at Cindy's and enjoy some much-needed AC. The view from their outdoor roof space is delightful! And once we started sweating again, we just went inside and were able to snag some bar seats. Turns out, you can even order food at the bar! We'll definitely be back next time we're in Chicago! read more

Cindy's Rooftop - View from the outdoor roof space - New American Near Me - Chicago, Illinois

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I went for a friends graduation brunch, and it was definitely a hopping spot in the city, and I can see the appeal for the rooftop views alone, but I think it's a bit overpriced for what you're getting in my opinion. I had the biscuits and gravy ($25) which was fine but also strange in that it tasted more like a chowder than gravy. I also got the chocolate chip cookies which were and came in an order of 3 for $12. As I said, a bit overpriced for cookies, but actually felt worth it for their size and deliciousness. Of course, part of why you're coming here is for the views and this place did not disappoint! Despite it being a very hot day outside, there was a good crowd out there especially because there's a bar on the patio as well. And even though it was very busy throughout the entire time there, my party and I had fairly consistent service, although I did have my drink order forgotten, but the server ended up comping me for it, which made up for it. read more

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

Great place to go see the bean from a rooftop view! The one thing that I didn't see in a lot of the reviews is that it's just a great view in general of Lake Michigan and Millennium Park and the amphitheater. Located in a hotel, there's an elevator that takes you straight to the top Would definitely recommend making a reservation if you're going to eat, even for a party of 1, as the bar wasn't too big, and was packed when I arrived. Ordered the espresso martini, bc, duh, and then made my way outside, as I was only there for the view! It is quite a beautiful view and hard to not just stay to soak up the view. The rooftop does not having seating, it's more for observation, and has a small ledge to set your drink on as you enjoy the views! If you can, make your way over, even if just for 10 mins for a drink and the views! read more

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Beautiful spot. Good service great view. Great cocktails. Was a very fun experience. Would recommend if you're in the Chicago area. read more

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

Definitely the best rooftop bar in Chicago. It's located in the Chicago athlete Association hotel, this is a great place to go and hang out. The building itself has a rich history. You definitely can wander around before making your way to the elevator to take you up to Cindy's rooftop. I went around four and it's was not very busy. I found a spot by the bar and immediately got help from the bartender. The best part of this bar are the views. The rooftop is made of glass you can see directly outside. There's also a patio where you can walk around with your drink and you can look over millennial Park. This place was recommended to me by a friend and I would definitely recommend it to anybody who is visiting Chicago for the first time. read more

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Getting a reservation was tough. I was trying for weeks! I did add my email to the waitlist in case something opened up and as it got closer to the date, you'll start receiving a ton of emails with availability. Be on the lookout as they will get booked fast! The place was a little smaller than expected. It is located on the top floor with amazing views!! The service was great and the food was amazing! We visited on a Thursday afternoon (around 5pm) and the place was BUSY! As for food, I got the SWEET CORN CAMPANELLE and it was so delicious and rich. It is filled with corn and bacon pieces. My husband got the Kurobuta Pork Collar and absolutely loved it. The beans were probably my favorite. Both plates were bigger portions and very filling. read more

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Amazing service as we only had 45 minutes before heading to the airport. Not an issue for this stellar team. We enjoyed the roasted carrots, the chicken sandwich and the lamb plate. All of the dishes were excellent, the service was friendly and the lake view was amazing. We will be back in September for dinner and a chance to sample from their wine list! Gracias! read more

I really thought Cindy's food was going to be overhyped but I am SHOCKED by how incredible this lunch was. We came during restaurant week and the dishes were fabulous. I started with the heritage grain bowl which was simple, fresh, and delicious. Nothing crazy impressive but I enjoyed all the different textures and the light, fresh dressing. What won me over was the fall squash orecchiette - this was everything I dream of in a pasta dish - mushrooms, squash, goat cheese, pumpkin seeds, and pesto. So delicious! And the s'mores baked Alaska was perfect in every way. I wasn't excepting to like it this much but I would definitely eat here again. read more

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

I came for lunch during a weekday. We were seated right away, ordering and getting our food was quick. The burger was pretty good and the views were great, even on a gray day. read more

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I've been to Cindy's so many times in the past and it has always been a great experience! Cindy's offers a beautiful views of the Millennium Park and majestic Chicago skyline. I make a point to bring my out of towner friends either to LH or Cindy's to enjoy good rooftop views of the city. My friend and I recently visited Cindy's on a weeknight and we ordered a Downtown train and Scotch on the rocks. Downtown train was a little too sweet but not bad! We could easily walk-in as it was a weekday but I recommend reserving the space if you're planning on visiting over the weekend. The same building where Cindy is located, you also have Milk Room, Game room and a lot more eateries to enjoy. I've never had food at Cindy's so cannot comment but drinks have always been good! read more

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