Cindy’s Rooftop | Chicago Athletic Association Hotel

Breathe in the fresh air and unmistakable ambiance when you dine at Cindy’s Rooftop. Enclosed by a revealing glass atrium overlooking Millennium Park with the blue waters of Lake Michigan in the background, let yourself escape the hustle and bustle of the busy Chicago streets. Upon stepping off the elevator and onto the top level of the Chicago Athletic Association Hotel, I was immediately transported to the middle of The Great Gatsby. I was struck by the light soaking through the glass atrium, filling the room with bliss. The wood furniture and mason jar flower arrangements added a rustic but elegant flair.

The Gatsby feeling only grew as our extravagant drinks came out I had the Reanimator: an iced drink with blueberry flavors and activated charcoal in it. The darkness of the drink was contrasted with the bright yellow flower placed floating on the ice. Not only was it visually captivating, but it is also deliciously refreshing.

Pro tip: another very Instagrammable drink is the Grey Garden. This drink has a foggy grey color and is complete with a beautiful purple flower.


Cindy’s drinks are not the only draw to this establishment. While their lunch menu is fairly thin, the offerings were so enticing that we struggled to make a choice! The staff is impressively trained to know all the details of each menu item and are happy to recommend something that best suits you. We ended up ordering Oysters on the Half Shell and Lamb Carpaccio as appetizers. The Fried Gunthrop Chicken Sandwich and Duck Confit constituted our main course.

Cindy’s prides itself on being a farm-to-table restaurant.  As a result the freshness of the food is unmatched! The oysters in particular were some of the freshest available in Chicago, served within 24 hours of being harvested. The Lamb Carpaccio was alsophenomenal. The lamb paired extremely well with the Mediterranean flavors of cucumbers, sun-dried tomatoes, and feta. This appetizer also came with warm and fresh pitas.

The drinks and appetizers already had me feeling full, but I was determined to try the rest of the order. I have never ate duck before, but found myself pleasantly surprised at its tender, delectable flavor. What stole the show on this dish was the savory tamarind barbecue sauce. If you never ate duck before, Cindy’s is a great place to try it.



If you’re not in the mood for duck, a popular lunch favorite is the chicken sandwich. It sells out every day, so grab it when you can! The sandwich was good, but the house made chips were ridiculously good.

No meal is complete without a sweet treat. The Cookie Board presented the kitchen’s take on some American classics like Oreos, S’mores, and PJ&J. Every bite felt nostalgic, taking me back to my childhood.

Everything about Cindy’s Rooftop is holistic, pure and well thought out. The beauty is in the details–beginning with the flowers they choose to put in your drink and ending with an original Warhol painting of Cindy Pritzker herself. While we had the opportunity to dine during lunch, they are open for dinner and weekend brunch as well. As it gets nicer out, you can just hang out on their terrace with a drink in your hand, soaking in the beauty of the most beautiful city in the world.

Cindy’s Rooftop
Chicago Athletic Association Hotel
12 S Michigan Ave, Chicago, IL 60603

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