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    Cindy's Rooftop

    4.1 (2.9k reviews)
    Closed 10:00 am - 11:00 pm
    Updated 1 month ago

    Cindy's Rooftop Reservations

    Cindy's Rooftop Photos

    Business Info

    CINDY'S ROOFTOP ATMOSPHERE

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

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    Recommended Reviews - Cindy's Rooftop

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    Reviews With Photos

    Second to None & Werner Wiener Circle Spicy
    Melanie L.

    They are reservation based and found a table on OpenTable and had limited availability but managed to snag a table in the afternoon. 5/5 ambiance - indoors has an open air seating with a rooftop patio view. You can grab a drink and go outside for pics which tons of ol ppl were doing. 4/5 Wiener Circle spicy - like a spicy margarita with Mezcal. Strong but well flavored. 5/5 mushroom toast - flavorful, cheese was perfect and flavor was amazing. 5/5 crème brûlée was delicious! The sugar was light and the custard was perfect. Menu is limited but everything was very well prepared. We had a bday noted in the reservation and they brought a free bday dessert with a candle which was a nice touch.

    Bloody Mary's
    Cindi B.

    This place is right across the street from Millennium Park. From the deck at Cindy's you can get a beautiful panoramic view of Chicago and Lake Michigan. Their Bloody Mary's are delicious and the bartenders are very attentive.

    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!

    Classic breakfast
    Emily F.

    Love this location! Went for brunch (recommend a reservation if you have somewhere to be). Great view, service and cocktails!! Recommend for a view of the city.

    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.

    Kelsie P.

    My sister and I went to Cindy's for breakfast and had drinks, an almond croissant, avocado toast, and the classic breakfast. Everything was delicious, but the almond croissant was my favorite. It had the perfect amount of almond flavor and was so good. The views were amazing too! Definitely make a reservation because it gets busy. We had a great time and would go back!

    View from Cindy's Rooftop
    Tara D D.

    My co-worker and I had lunch here this week and I'm never disappointed! The food was great and the service is always pleasant! The atmosphere is one of the best in the city, so if you're from out of town or have never been.....this is a must see view of the city!

    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.

    Monkey Bread

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    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!.

    View All 48 Questions

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    This was my second visit to The Dearborn, and the food and service were both on point. We ordered…read morethe salmon tataki, fish and chips, Wellington burger, and Midwest fried chicken. Everything was well prepared, but the fried chicken was the standout, especially with the hot sauce adding another level of flavor. The staff stayed attentive throughout dinner and even replaced our plates between rounds, which was a level of service I wasn't expecting. I also respected seeing the owner personally making the rounds, stopping at every table to check on the guests and the food. Calm atmosphere, solid hospitality, and a kitchen that delivers.

    OMG! Walk, run, sprint here to get the FISH N CHIPS THAT ACTUALLY BEAT BOBBY FLAY. The executive…read morechef and now chef partner, Aaron Cuschieri, is absolutely amazingly talented. I am used to really good fish and chips... I've never had better fish and chips than Tom Douglas's Mr. Fish in Seattle, UNTIL NOW!!!! Wow, wow wow wow! Do not pass GO, do not read the menu, just order the darn fish and chips! It might be a whole heart attack on a plate... But it doesn't matter... You can walk all of Chicago and burn it off. I decided to work out before I came here for this big splurge and I'm so glad I did. I can see that this is the theater district... And you could come here before a show fish and chips and have the best night of your entire life! I can't wait to try more of this chef's food! I'm BEYOND INSPIRED! ps great beers here toooooi!

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    Bar Mar

    Bar Mar

    4.3(651 reviews)
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    A fun place to get some seafood after work…read more Tuna ceviche, Asian taco, Salmon, Sea Bass. It was all good. The salmon was some of the best I've had, not overcooked at all. The taco in the Asian taco is seaweed. Its a small dish, but tasty. The ceviche was also excellent. The wine list is pricey but there are some values off the beaten path - the Bibei Lapola white from Spain pairs well with seafood. We passed on dessert but were generously comped the Key Lime Pie. It was deconstructed into piles of crust, merengue kisses, and foam. It was good. Service is friendly and professional, the space has an upbeat energy without being too loud, and the two story glass walls make for great viewing of the River and skyscrapers. Extensive outdoor space, but our visit corresponded with one of this summer's many heat waves, so we ate indoors.

    This place was very hit or miss…read more The cocktails were decent and interesting. The sloppy joe was pretty good, very quirky take. Jose's tacos were tasty with the caviar but nothing incredible. And the coconut tuna ceviche lacked in coconut. Neptune's pillows were bad. The tuna was super mushy and a bad texture, skip this. The muscles were a'ight. The Sea bass was okay but the sauce sucked. The $6 chips in olive oil were literally potato chips in a bag. The flan was great. The prices were high. The staff was iffy. Weird dude at front door... Then our waiter didn't give us any complimentary peanuts when we got there or caramel's when we left... that bothered me. Meh

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

    Joe's Seafood, Prime Steak & Stone Crab

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    Went yesterday to celebrate my 40th birthday. The service was impeccable. From the high-five I…read moregot at the Host stand to the well-wishes on my way out the staff made the experience very enjoyable and memorable. Our server, Jacob, was helpful and his recommendation of the Lyonnaise Potatoes did not disappoint. We had the small whale, an aged ribeye sandwich, and I got the filet mignon with bone marrow butter. The chilled seafood was delicious, especially with the house mustard sauce. My partner said the steak sandwich was the best they ever had. The filet was easily the best steak I've ever had though the dry-aged ribeye at Abrasado in Mendoza, Argentina is a close second. The grand martini was a perfect pairing for the chilled seafood. They threw in a complimentary brownie with ice cream for a bday dessert which was appreciated on multiple levels. We're not affluent and a meal like this was definitely a splurge but I have zero complaints and would 100% come back for a comparable special occasion. Everything was perfect and I'll remember this meal forever. Thanks, Joe's!

    In a word, phenomenal! The service was wonderful. We were in on a Saturday night and it was very…read morebusy. We ended up getting sat about 10 mins after our reservation. It's definitely busy and noisy. The stand out was the food. Wow! We had oysters and shrimp. Both so flavorful and delicious. I got the steak with the crab oscar, both were amazing. The grilled tomatoes, mashed potatoes, and corn (from the market menu) were all very good. I will dream about that corn.

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    Lowcountry South Loop - Seafood broil

    Lowcountry South Loop

    3.9(494 reviews)
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    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.

    Never heard of a self serve seafood boil bag place, that was different. If you don't want to do…read more"self serve", you have the option of sitting at the bar which charges a service fee. Service fee at bar is $16 dollars and some change. Quality of seafood was subpar at best, the snow crab was overcooked and the "Everythang" sauce was nasty, in general the sauce was too thick for my liking. No Dungeness crab only snow crab. No black mussels only green mussels. Bill was high for nothing, overly priced. The service was poor and also irritating. Obviously a bar maid attending to guests who are eating is not such a great idea. Non attentive, and well as taking shots with customers. I've eaten at many seafood establishments and this is the worst boil bag seafood place I've ever patronized.

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    Ocean Prime - Steak and shrimp scampi, a surf and turf entrée from Ocean Prime

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    4.4(472 reviews)
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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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    Acanto - Short rib rigatoni

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    4.3(701 reviews)
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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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    Cindy's Rooftop - newamerican - Updated September 2026

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