Chicago Loop, Rooftop

Cindy’s at the Chicago Athletic Association Hotel

Chicago Loop, Rooftop

Photo: Chritiques at Cindy’s at the Chicago Athletic Association Hotel

Want the best view in Chicago, all while sipping some fantastic drinks and enjoying some delicious food? Then immediately head to Cindy’s at the new Chicago Athletic Association Hotel.

Chicago Loop, Rooftop

Photo: Chritiques at Cindy’s at the Chicago Athletic Association Hotel

The Chicao Athletic Association (“CAA”) recently finished renovations, reopening their newly completed facilities to the general public after existing as a private club for decades. It now boasts one of the best rooftops in Chicago, with superb views and all-weather access. Formerly an exclusive private club dating back to the 1890’s, the CAA recently underwent a complete makeover and renovation and reopened to the public as the Chicago Athletic Association Hotel.

Chicago Loop, Rooftop

Photo: Chritiques at Cindy’s at the Chicago Athletic Association Hotel

In addition to the wonderful Venetian Gothic architecture and design, the hotel now boasts one of the best rooftops in the city, with unparalleled views of Millennium and Grant Parks, The Art Institute, and Lake Michigan.

Chicago Loop, Rooftop

Photo: Chritiques at Cindy’s at the Chicago Athletic Association Hotel

I recently dined at Cindy’s, the all-weather rooftop restaurant that also offers an open-air terrace, and I plan to make it a regular stop during my summer outings. Dishes are on the expensive side – you do not get that view for free, after all – but everything comes in large portions and is meant to be shared, and you can also order most items in half portions. We started with the fantastic and creamy Burrata cheese, spread atop a mound of asparagus and other seasonal vegetables, and served with the most delicious warm and buttery toasted bread. I would have been completely content with this dish and a glass of wine for the evening.

Chicago Loop, Rooftop

Photo: Chritiques at Cindy’s at the Chicago Athletic Association Hotel

We were also incredibly pleased with the quinoa salad, with squash and goat cheese. The salad was tasty, and dressed just perfectly.

Chicago Loop, Rooftop

Photo: Chritiques at Cindy’s at the Chicago Athletic Association Hotel

Finally, we also enjoyed the market crudo, which was Hamachi on our visit. Presented with Serrano chilis, corn, and an avocado mouse, the Hamachi just melted in our mouths and was a perfect dish for summer.

Chicago Loop, Rooftop

Photo: Chritiques at Cindy’s at the Chicago Athletic Association Hotel

During peak times – after work during the week and prime dining hours on the weekends – be prepared to wait in line in the hotel lobby just to get upstairs. Once there, once again be prepared to wait for a seat, and for a drink. However, time will pass quickly once you start taking in the gorgeous architecture and stunning views. And, the creative cocktails and delicious food make the wait worthwhile.

Chicago Loop, Rooftop

Photo: Chritiques at Cindy’s at the Chicago Athletic Association Hotel

Cindy’s open at 3 p.m. Monday through Friday, and at 10 a.m. on the weekends for brunch service. Reservations are accepted for parties of 4 or more.

Cindy’s at the Chicago Athletic Association Hotel

Michigan Avenue, Chicago, Illinois

Tastefully,

Christina

  • Nicholas Kadar

    what’s the wine list like?

    • I was quite pleased and thought that it was very well curated. I visited on a warm day during the summer, so I enjoyed a nice crisp sparkling rose.