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Cindy's Rooftop, Chicago, IL

Cindy's Rooftop

4.5
4.5
28 Reviews
$31 to $50
Contemporary American
12 S Michigan Ave, Chicago, IL 60603

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2 people
19:00
Booked 116 times today
  • Lively
  • Great for brunch
  • Great for scenic views
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.

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Additional information

  • Dining style
    Casual Elegant
  • Price
    $31 to $50
  • Cuisines
    Contemporary American, Comfort Food, Seafood
  • Hours of Operation
    Mon–Thu 11:00–23:00 Fri 11:00–00:00 Sat 10:00–00:00 Sun 10:00–23:00
  • Phone number
    (312) 792-3502
  • Website
    https://www.cindysrooftop.com/
  • 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.
  • Location
    12 S Michigan Ave, Chicago, IL 60603
  • Area
    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
    Gluten-free Options, Indoor Fireplace, Outdoor Firepit, Vegan

Menu

On the Lighter Side

  • Oysters on the Half ShellUS$4.00

    Chef’s Selection Of Oysters, Dressed With Seasonal Mignonette

    • Granola BowlUS$16.00

      House Granola, Greek Yogurt, Fresh Fruit, Maple

      • Avocado ToastUS$23.00

        Kale Pesto, Parmigiano, Pickled Fresno & Shallot, Sundried Tomato, Toasted Sourdough

        • Smoked SalmonUS$23.00

          Scallion & Dill Cream Cheese, Cucumber, Radish, Parsley, Toasted Sesame Bagel

          • Chef's SaladUS$16.00

            Baby Iceberg Lettuce, Hard Boiled Egg, Radish, Cucumber, Tomato, Bacon, Pickled Shallot, Cotija, Tajin Breadcrumb, Chipotle Ranch Dressing

            • Salmon CarpaccioUS$24.00

              Pear Aguachile, Pistachio Salsa Macha, Dill, Pickled Shallot

              Eggs

              • Cindy’s Breakfast PlatterUS$22.00

                Choice of Breakfast Sausage or Bacon, Scrambled Eggs, Home Fries

                • ChilaquilesUS$27.00

                  Poblano Salsa Verde, Braised Chicken, Corn, Chihuahua Cheese, Cilantro, Crema, Sunny Side Eggs

                  • QuicheUS$20.00

                    Chef’s Seasonal Preparation, Pickled Fennel & Seasonal Greens

                    Comfort

                    • Stuffed French ToastUS$27.00

                      Maple Glazed Croissant, Cream Cheese, Seasonal Jam & Berries, Cashew Mascarpone Mousse, Brown Butter Crumble

                      • Chicken and WafflesUS$28.00

                        Bourbon Butter, Hot Honey, Maple Syrup

                        • Biscuits and GravyUS$25.00

                          Homemade Herb Biscuits, Pork Sausage Gravy

                          • Not So Secret Secret BurgerUS$26.00

                            Butterkase Cheese, Lettuce, Tomato, Cherry Bomb Aioli, Brioche Bun, Fries

                            • Braised Pork Croque MadameUS$32.00

                              White Kimchi, Sriracha Aioli, Fontina, Milk Bread, Sunny Side Eggs

                              Sides

                              • BaconUS$8.00

                                • SausageUS$8.00

                                  • Scrambled EggsUS$8.00

                                    • Home FriesUS$8.00

                                      • Vegan ChorizoUS$12.00

                                        Sweets

                                        • Seasonal SorbetUS$8.00

                                          Chef’s Selection

                                          • DoughnutUS$8.00

                                            Chef’s Seasonal Preparation

                                            • Fresh Baked CookiesUS$12.00

                                              Chocolate Chip, Maldon

                                              • Sweet Potato Sticky BunUS$16.00

                                                Piloncillo Toffee Sauce, Spiced Pecans, Toasted Marshmallow Fluff

                                                Brunch + Lunch Beverages

                                                • DIY Mimosa

                                                  served with fresh berries and assorted juice

                                                  • Francois Montand Brut NV, Jura, FranceUS$75.00

                                                    • Champagne Drappier ‘Carte d’Or’ NV, Aube, FranceUS$125.00

                                                      • Bloody MaryUS$18.00

                                                        choice of: titos vodka, mezcal unión, linie aquavit

                                                        • Qahwa CoffeeUS$18.00

                                                          reyka vodka, broghetti, kyoto cold brew, demerara, green cardamom

                                                          Coffee

                                                          • Drip CoffeeUS$4.00

                                                            • EspressoUS$5.00

                                                              • Iced Estate Black TeaUS$5.00

                                                                • Latte/CappuccinoUS$6.00

                                                                  • Matcha LatteUS$8.00

                                                                    • Kyoto Black Cold BrewUS$7.00

                                                                      Tea

                                                                      • Rare Tea CellarsUS$8.00

                                                                        • Crema Earl Grey

                                                                          • Cloud Kissed Green

                                                                            • Regal English Breakfast

                                                                              • Mint Meritage

                                                                                • Emperor’s Chamomile

                                                                                  Last updated: 24 February 2025

                                                                                  What 28 people are saying

                                                                                  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
                                                                                  • 4.5Service
                                                                                  • 4.8Ambience
                                                                                  • 4.1Value

                                                                                  Noise • Moderate

                                                                                  Review summary

                                                                                  AI-generated from verified diner reviews
                                                                                  Cindy's Rooftop offers an "amazing view" of Millennium Park and Lake Michigan, making it a top destination for visitors. The atmosphere is lively, with a "trendy and hip" vibe. While some find the menu limited, the food is often praised as "delicious" and "creative." Service experiences vary, but the cocktails are "exceptional." Ideal for special occasions and impressing out-of-town guests.
                                                                                  417 Reviews

                                                                                  1. David

                                                                                    Washington DC3 reviews

                                                                                    2.0

                                                                                    Dined today

                                                                                    1. Overall 2
                                                                                    2. Food 5
                                                                                    3. Service 2
                                                                                    4. Ambience 3
                                                                                    A disappointing experience. The food was good but the atmosphere was tired and service wasn’t up to the standard of a restaurant of this caliber.

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                                                                                  2. Cindy

                                                                                    Richmond1 review

                                                                                    5.0

                                                                                    Dined today

                                                                                    1. Overall 5
                                                                                    2. Food 5
                                                                                    3. Service 5
                                                                                    4. Ambience 5
                                                                                    We loved going during our girls trip! I had a birthday, and they gifted me some chocolate mousse. Overall, the experience was lovely. The food was delicious (the sauce that comes with the steak frites in particular…) We loved the energy! That’s what a rooftop is for!

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                                                                                  3. Madeline

                                                                                    Nashville1 review

                                                                                    5.0

                                                                                    Dined 1 day ago

                                                                                    1. Overall 5
                                                                                    2. Food 5
                                                                                    3. Service 5
                                                                                    4. Ambience 5
                                                                                    They say they limit dining time to 2 hours for parties of 4 and up, but I can’t imagine using less than that time. We ordered a round of drinks, an app, entrees, and one more round of drinks. That took a full 2 hours, even with an early reservation of 5pm. But, maybe that was because of an off night where our first drink order got lost in the shuffle and pushed everything back. Otherwise, the food and drinks were great, the portions were WELL worth the price, and our servers were attentive and nice.

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                                                                                  4. 純淳

                                                                                    Greater Taipei3 reviews

                                                                                    5.0

                                                                                    Dined 1 day ago

                                                                                    1. Overall 5
                                                                                    2. Food 5
                                                                                    3. Service 5
                                                                                    4. Ambience 5
                                                                                    Thanks for call me back for the charge! I really appreciate it. Chicago is my favorite city and also Cindy is my favorite restaurant in these city. Whether the food, view or atmosphere all are the best. Thanks again!

                                                                                    Is this helpful?

                                                                                  5. Oscar VIP

                                                                                    Chicago55 reviews

                                                                                    5.0

                                                                                    Dined 2 days ago

                                                                                    1. Overall 5
                                                                                    2. Food 5
                                                                                    3. Service 5
                                                                                    4. Ambience 5
                                                                                    Such a great location! Even in a rainy day with thunder storms it was ideal. The service was stupendous. The team approach that have at Cindy’s was flawless. We had the grilled gem salad with avocado and it was delicious. It was a light lunch but it was exactly what we wanted. Cindy’s is a locals favorite but if you are in from out of town, it is a must place to eat and drink at.

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                                                                                  6. Evan VIP

                                                                                    Chicago16 reviews

                                                                                    3.0

                                                                                    Dined 5 days ago

                                                                                    1. Overall 3
                                                                                    2. Food 3
                                                                                    3. Service 3
                                                                                    4. Ambience 4
                                                                                    Fairly loud, especially for a Sunday brunch, making conversation a challenge. The view from the restaurant was quite spectacular. The food items our party selected were good, not great.

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                                                                                  7. Amie

                                                                                    Coastal Georgia4 reviews

                                                                                    5.0

                                                                                    Dined 6 days ago

                                                                                    1. Overall 5
                                                                                    2. Food 5
                                                                                    3. Service 5
                                                                                    4. Ambience 4
                                                                                    Food was delicious, server was great and very attentive the view from the balcony spectacular

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                                                                                  8. Boyd and Amylynn VIP

                                                                                    Orlando9 reviews

                                                                                    4.0

                                                                                    Dined 6 days ago

                                                                                    1. Overall 4
                                                                                    2. Food 3
                                                                                    3. Service 3
                                                                                    4. Ambience 5
                                                                                    There was no indication that there was nightshade in my meal- I am quite allergic to. Onions…I can handle the sweet onions without complaint so not that. I avoid tomatoes so it was not that… It was so spicy -peppers— that I could not eat my dinner. The waiter didn’t come by till my husband was nearly finished eating. So my husband ate mine too. He said there wasn’t much lobster at all in my dish. I ate his mushroom side and some of his dessert. I mean we’ll be back we love the vibe there but I didn’t get supple and we did not want to make a fuss. 38$ for something I can’t eat hits hard.

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                                                                                  9. Deb

                                                                                    Seattle27 reviews

                                                                                    5.0

                                                                                    Dined on 27 March 2025

                                                                                    1. Overall 5
                                                                                    2. Food 5
                                                                                    3. Service 5
                                                                                    4. Ambience 5
                                                                                    What incredible food in a gorgeous setting! Everything was delicious.

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                                                                                  10. James

                                                                                    Charleston2 reviews

                                                                                    4.0

                                                                                    Dined on 26 March 2025

                                                                                    1. Overall 4
                                                                                    2. Food 5
                                                                                    3. Service 5
                                                                                    4. Ambience 5
                                                                                    Outstanding dinner, service, and views. A little noisy.

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                                                                                  FAQs

                                                                                  Cindy's Rooftop is rated 4.5 stars by 28 OpenTable diners.

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

                                                                                  Make a booking

                                                                                  2 people
                                                                                  19:00
                                                                                  Booked 116 times today
                                                                                  Google Map for Cindy's Rooftop

                                                                                  12 S Michigan Ave, Chicago, IL 60603

                                                                                  Additional information

                                                                                  • Cross Street
                                                                                    Madison & Michigan Avenue
                                                                                  • Area
                                                                                    Downtown / Loop
                                                                                  • Hours of Operation
                                                                                    Mon–Thu 11:00–23:00 Fri 11:00–00:00 Sat 10:00–00:00 Sun 10:00–23:00
                                                                                  • 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
                                                                                    Gluten-free Options, Indoor Fireplace, Outdoor Firepit, Vegan
                                                                                  • Website
                                                                                    https://www.cindysrooftop.com/
                                                                                  • Phone number
                                                                                    (312) 792-3502
                                                                                  • 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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