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Cindy's Rooftop, Chicago, IL

Cindy's Rooftop

4.5 (53)
$31 to $50
Contemporary American
12 S Michigan Ave, Chicago, IL 60603

Make a reservation

2 people
7:00 PM
Booked 89 times today

About this restaurant

  • Great for scenic views
  • Good for special occasions
  • Lively
Perched atop the 13th floor of the Chicago Athletic Association hotel under a glass atrium, Cindy's welcomes guests with sweeping views of Millennium Park, the ever-changing blues of Lake Michigan, and beyond. Providing a remarkable backdrop for Top Chef contestant Executive Chef Kaleena Bliss and her inspired menu featuring local wild and seasonal produce and fresh seafood. With vibrant service, an all-season terrace, and an extensive beverage menu that intertwines naturally with the dishes, every detail of your experience is thoughtfully crafted to make a lasting memory.

For private events: please reach out to cindysevents@caa.bokagrp.com.

Additional information

  • Dining style
    Casual Elegant
  • Price
    $31 to $50
  • Cuisines
    Contemporary American, Comfort Food, Seafood
  • Hours of operation
    Mon–Thu 11:00 am–11:00 pm Fri 11:00 am–12:00 am Sat 10:00 am–12:00 am Sun 10:00 am–11:00 pm
  • Phone number
  • Payment options
    AMEX, Diners Club, Discover, Mastercard, Visa
  • Dress code
    Smart Casual
  • Executive chef
    Kaleena Bliss
  • Private party facilities
    From private parties to corporate events, Cindy's is one of Chicago's best event spaces. Our world-renowned view, impeccable service & seasonally fresh menu make our enclosed rooftop one of the best restaurants with private rooms in the city. Event spaces include: semi-private Lakeview couches, private Library dining room & full restaurant buyouts.
  • Neighborhood
    Downtown / Loop
  • Cross street
    Madison & Michigan Avenue
  • Parking details
    Valet is located on our Madison Street entrance in between Wabash and Michigan.
  • Entertainment
    The Library, our private dinning room that will house small dinners, events, mixology and chef tastings/classes for guests.
  • Additional
    Bar/Lounge, Beer, Cocktails, Corkage Fee, Counter Seating, Full Bar, Gender Neutral Restroom, Gluten-free Options, Indoor Fireplace, Non-Smoking, Outdoor Firepit, Patio/Outdoor Dining, Private Room, Vegan, View, Weekend Brunch, Wheelchair Access, Wine

What 53 people are saying

Cindy's Rooftop reviews from people who’ve dined at this restaurant. Based on recent rating.

Overall ratings and reviews

Reviews can only be made by diners who have eaten at this restaurant

4.5
4.5 based on recent ratings
  • 4.4Food
  • 4.4Service
  • 4.7Ambience
  • 4Value

NoiseModerate

Review summary

AI-generated from verified diner reviews
Cindy's Rooftop offers stunning views and a chic atmosphere, making it a "must see in Chicago." Guests rave about the "great cocktails" and "friendly staff," enhancing the dining experience. The menu can be limited, but highlights include "amazing drinks" and "delicious food." Service can be slow during busy times.

441 Reviews
  1. Jen VIP

    Milwaukee6 reviews

    3.0

    Dined 3 days ago

    1. Overall 3
    2. Food 4
    3. Service 1
    4. Ambience 4
    Service was terrible. He was inattentive and rarely stopped by. We waited at least 20 min to order our drinks, then decided to order everything at once because we weren’t sure when he’d be back. It took an additional 20 min to get our drinks (glass of wine). We ordered rolls to come out before our meal and they came with our meal. Something as simple as that shouldn’t have needed 30+ min to prepare. He never checked on us and we had to get his attention to order dessert and two additional glasses of wine. Don’t give someone a time limit then take so long we were barely even able to dine within the 2 hours. I’ve been to Cindy’s many times, but I’m not sure I will return.

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  2. Taylor

    New York City2 reviews

    2.0

    Dined 4 days ago

    1. Overall 2
    2. Food 3
    3. Service 1
    4. Ambience 5
    Our waiter seemed annoyed that we were there. Brought the wrong drinks and was rushing anytime he spoke to us. One person in the party got a burger was never asked how it was cooked and just brought it out and it was too rare for liking. The rest of the party ordered salad and one side of bacon, which was undercooked and rubbery. The salads were extremely tiny for $20 with nothing but lettuce and dressing and some of the lettuce was . Would have been better off, going to the grocery store and buying a salad kit. I’ve been here before and it was way better, but I will not planning to go back for food. Waste of money. 

    Is this helpful?

  3. steven

    Detroit2 reviews

    1.0

    Dined 4 days ago

    1. Overall 1
    2. Food 1
    3. Service 1
    4. Ambience 5
    Our food - it’s like our words were disregarded and a different meal came. Al thought it was comped it did alter the experience. We were not checked on during meal and had to flag staff. . Very cool place but to me was all hype. Undeniably very pretty. Kind staff.

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  4. Celso

    Unspecified1 review

    5.0

    Dined 5 days ago

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Awesome service! Amazing drinks, food and desert! Perfect rooftop city view!

    Is this helpful?

  5. Andrew

    Montreal1 review

    4.0

    Dined 6 days ago

    1. Overall 4
    2. Food 5
    3. Service 5
    4. Ambience 5
    really great, loved it, and must see in chicago. great view

    Is this helpful?

  6. Lisa

    Chicago3 reviews

    5.0

    Dined 7 days ago

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    One of the best rooftops in the city! Views are amazing, food was tasty too. Would love to try Brunch!

    Is this helpful?

  7. gabriella

    Chicago1 review

    1.0

    Dined on April 22, 2025

    1. Overall 1
    2. Food 1
    3. Service 3
    4. Ambience 2
    I came here today for my golden birthday and was very disappointed with the food. I bit into the chicken and it was literally brown I couldn’t even chew it I had to spit it out. Looks like I bit into a squid. Everyone sat so close to each other shoulder to shoulder. When making the reservation I put a birthday as the occasion and there was absolutely no acknowledgement. Why ask for the occasion if you won’t accommodate that.. even a happy birthday would be nice. The view was the only nice thing.

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  8. Beatriz

    Madrid3 reviews

    5.0

    Dined on April 22, 2025

    1. Overall 5
    2. Food 4
    3. Service 5
    4. Ambience 5
    The food was great, especially the chicken and the carrots! Nice spot with amazing views. But we would like to recommend/suggest something on the artichokes: the artichoke was almost raw, hard to bite. The only part which could be eaten was the artichoke's heart, which was not particularly tasty either and their price was almost $20 for three artichoke's hearts. A longer grill time might be needed to enrich and make the artichokes tastier.

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  9. Tina

    San Francisco2 reviews

    5.0

    Dined on April 21, 2025

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Just lovely!!!! What a unique space! Will definitely go again!

    Is this helpful?

  10. Chelsea VIP

    Greater Boston2 reviews

    5.0

    Dined on April 21, 2025

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Always love Cindy’s! Best food and cocktails in Chicago!!!

    Is this helpful?

FAQs

Cindy's Rooftop is rated 4.5 stars by 53 OpenTable diners.

Yes, you can generally book this restaurant by choosing the date, time and party size on OpenTable.

  1. Home
  2. United States
  3. Chicago / Illinois
  4. Chicago
  5. Downtown / Loop

Make a reservation

2 people
7:00 PM
Booked 89 times today
Google Map for Cindy's Rooftop

12 S Michigan Ave, Chicago, IL 60603

Additional information

  • Cross street
    Madison & Michigan Avenue
  • Neighborhood
    Downtown / Loop
  • Hours of operation
    Mon–Thu 11:00 am–11:00 pm Fri 11:00 am–12:00 am Sat 10:00 am–12:00 am Sun 10:00 am–11:00 pm
  • Price
    $31 to $50
  • Cuisines
    Contemporary American, Comfort Food, Seafood
  • Dining style
    Casual Elegant
  • Dress code
    Smart Casual
  • Parking details
    Valet is located on our Madison Street entrance in between Wabash and Michigan.
  • Payment options
    AMEX, Diners Club, Discover, Mastercard, Visa
  • Executive chef
    Kaleena Bliss
  • Entertainment
    The Library, our private dinning room that will house small dinners, events, mixology and chef tastings/classes for guests.
  • Additional
    Bar/Lounge, Beer, Cocktails, Corkage Fee, Counter Seating, Full Bar, Gender Neutral Restroom, Gluten-free Options, Indoor Fireplace, Non-Smoking, Outdoor Firepit, Patio/Outdoor Dining, Private Room, Vegan, View, Weekend Brunch, Wheelchair Access, Wine
  • Phone number
  • Private party facilities
    From private parties to corporate events, Cindy's is one of Chicago's best event spaces. Our world-renowned view, impeccable service & seasonally fresh menu make our enclosed rooftop one of the best restaurants with private rooms in the city. Event spaces include: semi-private Lakeview couches, private Library dining room & full restaurant buyouts.
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