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    Cindy's Rooftop

    4.1 (2.9k reviews)
    Open 10:00 am - 11:00 pm
    Updated 2 weeks ago

    Cindy's Rooftop Reservations

    Cindy's Rooftop Photos

    Business Info

    CINDY'S ROOFTOP ATMOSPHERE

    What's the vibe?
    Moderate noise
    Trendy
    Good for groups
    Outdoor seating

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    Recommended Reviews - Cindy's Rooftop

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    Menu
    Melissa W.

    After an afternoon of sightseeing (& sweating in the heat), we were very excited for a cold beverage on the rooftop. Cindy's has a large outdoor patio with standing room overlooking Millennium Park and the bean. Such a great location! The drinks were delicious & the service was great. We wished we had time to enjoy a second beverage but we will definitely be back!

    sourdough for burrata
    Cady D.

    I love Cindy's!! I think this was my third time here. It's probably one of my favorite rooftop bars in Chicago. The service is always good, the vibes are fun, and the rooftop view is one of the best. If you come in the summer, the rooftop has a bar so you don't have to keep going in and out, but you're allowed to take your drinks from the inside bar to the rooftop. It gets a bit crowded out there and there are no seats or places to set your drink down. I prefer coming in the early evening so I can enjoy the clear view of millennium park. At night you can't see as much. I also prefer coming here in the winter because it's a lot less crowded and you'll basically have the rooftop to yourself. They also have cozy fires on the rooftop during the winter. We came here recently for a late night snack and dessert and drinks. As my drink, I ordered the Cha-Cha-Chicago, which was kinda like a pina colada with blueberry and super refreshing! For food, we ordered burrata, carrots, and the macchiato noir. The kitchen closes at 10pm (two hours before the bar closes). We got there around 9:30 and were able to order food no problem. The burrata was delicious and refreshing! The carrots were also good. We asked if dessert ended at 10pm too and couldn't really get a clear answer from anyone, but we ordered around 9:55. Although the bartender forgot to put our order in after we asked him, we still got our dessert after 10pm. We ordered the Macchiato Noir and it was so delicious and tasted like salted caramel and coffee. Our bartender offered us complimentary sips of Amaro (probably as a way to apologize for forgetting to put in our dessert), but that was really nice of him. We took them outside to enjoy on the rooftop.

    Classic breakfast
    Emily F.

    Incredible venue with great views of the city. Cocktail menu was especially great due to the adjective listing under each of their specials. Enjoyed the Emerald Mile along with the classic breakfast (gluten, dairy free). Server was great. Be prepared to be put on a waitlist (didn't take too long). This place is sought after due to its location.

    Monkey Bread
    Sabrina S.

    First time in Chicago and I had to come to Cindy's due to the raving reviews and videos I've seen online! Let me say the view and restaurant were beautiful and the service was great. My three star review is for the lack luster food. After experiencing all the incredible food in Chicago I was disappointed with the quality and taste of the food at Cindy's. The shrimp in the shrimp and grits was overcooked, the monkey bread tasted stale, the chilaquiles were soggy, and the avocado toast was bland. If you're looking for an aesthetic place to take pictures and enjoy the view this place is great!! I wouldn't come back for the food. :)

    Dessert peach orchard
    Tigui D.

    Loved everything about our experience! The location is incredible- we had our lunch overlooking Millennium Park. We came here on a Friday for our 2pm reservation. We got seated outside. Our waiter was Ian, he was amazing at his job. He knew the menu extensively and describe everything well. He treated us like we were friends. The food was surprisingly delicious- we ordered the oysters, shrimp roll, and smash burgers! It was delicious. For dessert we tried the peach orchard- it was an interesting dessert, it had a lot going on. It was big, enough for two people, maybe three. It was an OK dessert, as soon as I ate I forgot about it. Overall, a great experience! I would love to come back for a girl's brunch or dinner!

    Ashley O.

    I went here with my boyfriend and the atmosphere was incredible. Post-grad life has us balling on a budget, so we shared fries, mussels (SO tasty), and two cocktails. The environment is... bustling to say the least, but has an amazing, intimate feel with the right person. We were seated along a row of two-seat tables, which felt slightly awkward and cramped, but there was space to go outside, take pictures, and enjoy your beverage/the view from there! We had a reservation, but I saw a couple people come in without one and they seemed to have no problem entering in. To be safe, I'd definitely recommend making one.

    Chilaquiles*
    Jonathan B.

    I'll start off with the ambiance and that it's totally worth the visit just for the view alone! You take an elevator to the rooftop level of a tall building in downtown, and you get to experience a view of the lake, millennium park, and much more! You definitely want to come during a nice day and take pictures. The food was decent. I will say that I got the chilaquiles, and I was getting really tired of the flavor; it was a little salty when I got it, and the chips were so mushy at one point. The eggs benedict on the other hand was delicious! The English muffin paired so well with the ham and egg, and the potatoes were to die for! They were warm, crispy, and flavorful. The service was great; the waiter gave us recommendations and always made sure our waters were full. Additionally, he made sure to check in with us through the meal. I'd definitely recommend coming here as an experience, but I will say the price of the food is a pricey for what you get.

    Menu
    Kirk B.

    Cindy's Rooftop was a very enjoyable experience, and I can absolutely see why it's such a popular destination. The views of the Chicago skyline are breathtaking and definitely the highlight of the restaurant. The menu is somewhat limited, but the food was very good. We ordered the signature smashburger and the cod fish sandwich, both served with crispy fries, along with gin spritzers. Everything was well prepared, flavorful, and satisfying. Our server was attentive and friendly throughout the meal. The only disappointing part of our visit involved the host. Our server had turned our table so both of us could enjoy the skyline view through the window. Later, the host approached us and said we couldn't have the table positioned that way. We explained that our server had been the one who turned it for us, which was true. The host walked away and never returned to clarify the situation or let us know if it was acceptable after all. That interaction left us feeling confused. As a same-sex couple sitting close together, we couldn't help but wonder if that influenced the interaction, although we have no way of knowing. A brief explanation or follow-up from the host would have gone a long way toward making us feel more comfortable. Overall, the incredible views, good food, and attentive service made for a memorable visit. Despite the awkward interaction with the host, I would return for the atmosphere alone.

    Avocado toast
    Andi H.

    Always a beautiful atmosphere, friendly staff, and elevated experience. Cindy's is one of those places that is just a bucket list places for great food, unique cocktails, and stunning views! The prices are a little high, but you have to remember youre downtown! I do love that you can have a drink outside on the patio without reservations. Reservations open up 14 days in advance and they go quickly!

    Rigatoni Alla Vodka $26.00 lemon ricotta, parmesan, basil
    Holly K.

    One thing I've learned turning almost 60... I'm traveling for the views, the food, and the memories--not to fight a crowd for a spot at the railing! (If you are young, dress up, enjoy the view, the music, the vibe (as one gentleman around 26 told me, so sweet), and the crowd. Cindy's, on the rooftop of the Chicago Athletic Association, is absolutely worth the visit. The sweeping views of Millennium Park and Lake Michigan are beautiful, and the food was every bit as impressive as the scenery.   Since we're vegetarians, we enjoyed some delicious meat-free dishes, including crispy arancini, a rich and flavorful rigatoni, and a chocolate dessert (The Rocker, I will say the baked Alaska did look amazing), that disappeared much faster than I'd like to admit. We paired it all with two refreshing mocktails (N/A Spritz $16.00 a non-alcoholic hugo, aperol or pathfinder spritz; bitter - citrusy - crisp and a KEVIN!! $18 seedlip garden 108, strawberry puree, lime, elderflower soda). The best surprise? Our mocktails were complimentary because our room couldn't be upgraded, and our credit card package included a beverage credit. We also had a $100 hotel dining credit to use during our stay. It's a good reminder to investigate travel credit cards--they can add some nice perks, especially if you pay the balance off every month. My biggest tip: make a reservation. The wait can get pretty long. We were lucky and only waited a few minutes. Could you grab a drink and stand outside? Sure. But honestly... that's a younger person's game! I'll happily trade standing shoulder-to-shoulder in a crowd for a comfortable table, great service, and a view I can enjoy. Age has taught me that comfort is underrated. Our server was friendly, attentive, and somehow always seemed to appear at exactly the right moment without hovering. If you're visiting Chicago, put Cindy's on your list. Be patient if you're walking in, order something you've never tried before, enjoy one of their creative drinks (with or without alcohol), and take a few minutes to soak in one of the best rooftop views in the city. Sometimes the best souvenirs aren't things you buy--they're the meals, the laughs, and the places you'll still be talking about long after the trip is over.

    Linda B.

    The only thing worth coming here for is the view. Ordered oysters which were so so and tiny for $25 for 6 and the $22 beat salad my toddler could have opened the canned oranges and canned beets himself! Service was ok. Up charge for what food costs? Prices are already inflated !! Find another rooftop as Chicago has many to chose from! Would not go back. We had to go to another restaurant for real food afterwards. Sad,

    Cindy
    Cherie G.

    All I can say is WOW! Last night in Chicago and what a perfect way to end it at Cindy's Rooftop. Make sure you get reservations ( 14 days before ). Can't miss it ! The views are incredible and make sure you come for nighttime views as well. We had the tuna tartare ( delish !) the strip steak was really great. The rigatoni vodka was in a special lemon whipped ricotta HEAVEN! Bread and herb app delish. I can't believe this mocktail !! Read up on who Cindy is if you don't know, her 1982 Warhol is prominent in the space. Thank you CINDY's!!! Xo FOX TOP PIcK Of Chicago!!!

    Skyline .
    Elizabeth S.

    Late night dinner and sips after the ghost gangster tour around Chicago! We picked Cindy's rooftop at the Chicago Athletic Association on the 13th floor for stunning skyline views which was the perfect spot to just unwind from the busy day. Though we couldn't see much of Lake Michigan, we knew it was just right there. We enjoyed the fresh Caesar salad, creamy Rigatoni alla Vodka, and warm bread with herbed butter. , and an espresso martini and a glass of prosecco. For dessert, we ordered the baked Alaska (So good), and coffees which ended the night with perfection. Service: Cheers to Anthony for the wonderful service and great menu suggestions!

    Caesar Salad with Salmon

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    2 years ago

    Did a private customer event in their private rooftop event space. The food and drinks were excellent and service was top notch!!

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    Really enjoyed everything! The food was tasty, and the staff was especially friendly. Great place:)

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    Page 10 of 72

    Cindy's Rooftop Reviews in Other Languages

    Ask the Community - Cindy's Rooftop

    Do I need reservations just to have drinks at the terrace, not for dining?

    I walked in without a reservation... Had a few beers on the terrace.

    Is there a dress code?

    No strict dress code. Attire runs the gambit. I went in the summer and folx had on shorts and tees, sundresses, jeans, and tees, etc... This was for brunch. I think snappy casual to business casual works for weekday lunch or dinner as well. It's a… 

    Lunch or Dinner for best views (sunset) and menu?

    Cindy's faces east so no sunset...it is a pretty view all day long. Patio may be more pleasant in the evening on a warm day...

    What's your preferred experience- Brunch or dinner?

    Dinner

    Do they accept walking?

    They do! But come early - even if you get there before they open and go up the first elevator, you might have to wait at the bar. I've walked in twice during opening and been seated within 15 minutes.

    Can you make reservations? Do you need to?

    Yes you can

    Good place for dinner conversation? Or, super loud and you need to yell to be heard?

    It is loud in the dining room, you can talk to the person next to you but have to talk loud or yell to heard on the other side of the table.

    Are kids allowed?

    I'd imagine so, but after 8:30 PM / 9 PM it might not be a "fit"...

    Is there a open bar?

    It's 'open' as in able to use but not as in free;)

    What is the Attire. Can you come casual?

    Yep, you can absolutely come casual. Not a formal place.

    Are you able to sit outside? Trying to make a reservation but it says indoors only? Weird

    No seating outside

    Could I show up for just a drink or two on the patio without reservations? Hoping to go Friday afternoon to show my out of town sister the space.

    I went about a week and a half ago and though it says you can't online, while I was there, they were allowing people to just show up and get a drink if there was space available.

    Is the outdoor patio open?

    Yes for viewing purposes only. You get like 15 min to look at the views.

    Kid menu? Wondering if they have anything off menu for kids

    Can't really say. I had the pleasure of dining only with other adults so didn't have to look for a grilled cheese or chicken nuggets. Although there were a surprising number of families with small children in attendance

    What time is happy hour?

    There isn't a happy hour, per se, but they do have a 'limited menu' from like 2:00-4:00 (or maybe 2:30-4:00) and it is just a couple of items/shareables. Even without a sunset view, it is well worth an afternoon visit, the lake view is amazing!

    Yelpers! What would you recommend for solo diners?

    There's a bar / countertop where a lot of people sit and hang out. Looked like a ton of fun. I almost got up from my table to go sit at the bar.

    You have to pay $65 to get in?

    Honestly though you can easily spend $65 when you leave there.

    Do you have to have a reservation for brunch?

    Yes, unless the popularity has fallen way off. I made a reservation three months out last summer.

    Do they serve burgers?

    No burgers.

    Do I need reservations OR a table to hang out on their patio? I'm wondering if I can just grab a drink and take in the view and then leave :-)

    You can just go hang out, no need for reservation!.

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    Joe's Seafood, Prime Steak & Stone Crab - Ahi Tuna Tartare*

    Joe's Seafood, Prime Steak & Stone Crab

    4.4(3.3k reviews)
    0.7 miNear North Side
    $$$$

    Crazy on a Monday night at 630 pm the place was packed!!…read more Classic Chicago steakhouse. It's lively and fun & the food is great! So is the service, excellent without being overbearing. We had a big party and most orders were a bit different. Everyone lived the apps, drinks and their dishes! Everyone was too stuffed to have desert. I had a perfectly cooked strip steak. It was delicious and the flavor was great! Shared a baked potato and the wonderful Mac & cheese. Mrs A liked it better than Swift and Sons - but that is still #1 for me - although it's in the west loop and not walkable if staying on MI Ave. Don't like the 3.5% for "rising" costs...seems like that has been around since COvID. I always catch it after I pay the bill...

    Joe's Seafood in Chicago has an unusual amount of personal history for me. It opened as a…read morepartnership between Miami Beach's iconic Joe's Stone Crab and Lettuce Entertain You, bringing South Florida to Grand and Rush. I first went when it was still a huge, buzzy Chicago spot, and one of my most memorable dinners came after my high school graduation in 2003. I even got a speeding ticket on Lake Shore Drive with my grandmother in the back seat on the way to dinner, which still makes me laugh. Chicago was an especially fun place for Joe's to arrive. Open outcry trading was still a force, and the wealth creation around it was wild: people who had dropped out of high school could become millionaires in their twenties, while math PhDs from the University of Chicago could make fortunes in the same ecosystem. It was a golden era for hustle culture, when commerce idolized Tony Montana in a way that today is more likely to idolize Jamie Dimon or David Solomon. Death Row and Bad Boy ruled the airwaves, while Michael, Shaq, Kobe, and Allen Iverson defined the NBA. Basketball was so dominant in Chicago culture during my coming of age that I still map other things, including restaurants, to NBA teams. Joe's felt like the Miami Heat coming to Chicago in much the same way Smith & Wollensky represented the New York Knicks: each brought a recognizable piece of its hometown culture into another major city. Joe's brought real South Florida sizzle to Chicago, and it landed at exactly the right moment. Going there felt like an occasion. Florida took longer for me to understand in full. My family has roots in the state going back decades, farther north along the Atlantic coast, and I didn't visit Miami until March 2007, when my sister started graduate school in Coral Gables. That trip began my love affair with Miami and helped me understand why the original Joe's was such an institution. A close family friend's father spent time around Miami in the 1960s and 1970s. He knew local fishermen who caught stone crabs, which gave me an appreciation for the older South Florida culture around the food, separate from Joe's own history. Another Joe's memory captures an entirely different moment. Looking through my OpenTable history, my July 31, 2008 reservation at Joe's in Chicago is the earliest reservation I can find at a restaurant that is still open today. I was 23, working at UBS, preparing to move to New York while the firm was already on fire from its mortgage losses, and Lehman would file for bankruptcy just weeks later. I was broke but wildly aspirational, dreaming about dinners at Balthazar, begging my way past the doors at Cain and Tenjune, hoping to drink for free, and trying to meet women comically far out of my league. Through all of those memories, the restaurant itself has been remarkably consistent. The stone crab claws are incredible, the seafood is excellent, and Joe's holds its own among Chicago's serious steakhouses. The room has traditionally felt a little more formal than Miami, with bow ties, polished service, and a darker old-school steakhouse rhythm, while still being genuinely welcoming. Finish with the key lime pie. Years later, my wife and I held our wedding reception at RPM Seafood, another Lettuce restaurant, then ate at the original Joe's during our honeymoon in Miami during COVID days later, which felt like a fitting circle back. In sheer range of venues, repeatability of quality and atmosphere, and consistency of hits, Lettuce is the gold standard in Chicago, with some of that same reach in Vegas and DC. I've been extraordinarily privileged in my exposure to hospitality, and I still repeatedly admire Rich Melman's model, taste, and execution, now carried forward by the next generation of the family. Joe's is a prime example: world-class, durable, unmistakably Chicago, and absolutely somewhere I want to return next time I'm in town with some dough to spend. While Joe's may not be French, this place still earns my highest marks: très bien!

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    Lowcountry South Loop - Seafood broil

    Lowcountry South Loop

    3.9(493 reviews)
    0.9 miSouth Loop
    $$

    I've never been a fan of the seafood boil dining thing, just too messy for me, but I must admit I…read moreenjoyed my visit and the food was really good. My daughter asked to come here so we came downtown on a Friday around 7:30pm and it was pretty crowded, but by it only being two of us our wait time was less than 10 minutes. Once seated you scan the QR code to look over the menu and once decided you go to one counter to place your food order and the bar to place your drink order, they then bring your food to the table and our food came pretty quick after ordering. Bib on, gloves on, time to dig in... My daughter ordered the bag with shrimp, crab legs, corn and potatoes and I ordered lobster tails, corn and potatoes and two lemonades (lemonades were delicious!) We ordered our food with the everythang sauce (which is a mix of all their sauces) and it was really good and really flavorful. Messy is to be expected but surprisingly the food mess was manageable and did not take away from my dining experience. The amount of crab legs in my bag to me did not justify $32 and if it wasn't for the potatoes and two corns I'm sure I would of still been hungry. Seafood boils are not a cheap experience neither, our meals with the two lemonades and no alcohol was $110, so definitely not an every weekend dining option, but leaving I did see on their info board that their shrimp, crab bags are $28 Monday - Thursday and they look to have a pretty good happy hour so this might be a reason for a quicker return. Overall my experience was pretty good.

    Have been wanting to try this place a while because I've passed it a lot. It's nice inside and is…read moreon par with other seafood boil restaurants. There on no waiters, you order at the register and they bring your food out to you. Both me and my wife got the crab cluster. I added sausage and the garlic noodles to mine. The crab was not fresh and the hot level seemed to be more than what I'm accustomed to. I got the 2nd level which I thought would be more mild, worth noting if you decided to get the hot spice level. The cornbread and the garlic noodles were decent but I couldn't really enjoy it because my mouth was burning. The strawberry lemonade was good. Overall, I wouldn't return due to the quality but I may have just caught them on a bad day and ordered the wrong spice level.

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    Ocean Prime - Twin Lobster Tails

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    I visited this beautiful restaurant last week during a business trip. I've been back home for days…read morebut continue to think about this place. It was an extraordinary experience, from the impressive service to the phenomenal food. And the presentation?! Top tier. The stars of the dinner... * Mercedes the AMAZING! * calamari * shrimp cocktail * the bread basket (especially the pretzel sticks with the perfectly-whipped butter) * filet mignon Oscar style * hot & dirty martini * warm butter cake * ...and the smoothest coffee to end the evening I hope to return to Chicago again in the future, next time with my husband. If I do, I'll be sure to make a reservation here because I know it would impress him just as much.

    This place is beautiful and provides top-notch service. ...but I was a tad underwhelmed with my…read moremeal. The lobster roll was good, but it came with fries, and half of them were overcooked, so they tasted bad. I expected more for the price. We did end the night with their warm butter cake, which was absolutely delicious. So, so good. I seriously cannot overstate how delicious it was; go get one. (BTW, when they ask if you want to start with bread when you're seated, it's not complimentary. LOL! We found that out when we got the bill. We actually would've gone with the calamari had we known we were choosing an appetizer by saying "yes" to bread, but we got full on the bread and decided not to get an appetizer...only to find out that we *had* gotten an appetizer.)

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    Ocean Prime - Butter cake

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    Acanto - Short rib rigatoni

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    4.3(699 reviews)
    0.0 miThe Loop
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    One of the best meals we had in Chicago. Excellent all around…read more The arancini were rich but also somehow light, the gnocchi were pillowy and soft. The gelato was creamy and delicious. Service was attentive but not smothering. (And as a vegetarian, I was glad to see they even marked their desert menu with dietary notations. It really increases my trust that a restaurant is run by people who know what they're doing when they know pana cotta isn't vegetarian.)

    The restaurant is not that far from the Art museum and Cloud Gate (aka The Bean)…read more We had reservations and were seated right away. They light a new candle on your table and it was fun guessing how many hours it takes for the candle to melt all the way down. We came during dinner time and sat inside. We shared the Arancini, usually comes in 3 and they made 4 for us, since there were 4 of us. Very delicious and we all just took our time savoring the flavor. So good and it is also GF made with rice flour. Next I had the Umbricelli con Sugo d'Anatra. House made spaghetti with duck meat. Noodles were firm and didn't twirl on the fork easily. But it was really good. There were plenty of duck meat shredded and chunks. The cherry tomatoes were a bit tart to me, so I didn't eat them all. For dessert we shared the Tortino al Cioccolato Valhrona, like a chocolate lava cake. Very soft and rich chocolate. Had orange pieces throughout. Came with coffee gelato. Also shared the Vanilla bean panna cotta. Smooth creamy and light, reminds me of crème brulee. Had lots of cherries with crumbles of cookies. Both desserts are GF. I actually like the chocolate more... couldn't resist. They cleanup and give you a new plate and or silverware after each course. They are very good at keeping your glass of water refilled. Very friendly staff.

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    Acanto - Bar

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    Arancino**

    Cindy's Rooftop - newamerican - Updated August 2026

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