The Chicago Athletic Association is an 1890s Venetian Gothic landmark turned 241-room hotel. Formerly a private men's club, the re-opening in May marked the first time the CAA was open to the public. While it is hard to tear yourself away from the insanely ornamental and remarkable interiors when you enter the CAA, be sure to beeline it to Cindy's, the brand-new 13th-floor rooftop space.
Cindy's Rooftop is without doubt the jewel in the crown of The Chicago Athletic Association Hotel. This rooftop restaurant and open-air terrace with panoramic views of Millennium Park, the Art Institute, Lake Michigan, and beyond is not to be missed. With seasonal freshness reflected in both food and drink, the rooftop dons the relaxed ambiance of a Great Lakes beach house with a view. Think Michigan beach house meets historic train shed. The outside terrace flanked by two big fire pits faces the lake with amazing views right over Millennium Park and the Art Institute. The inside is just as beautiful: Find long cherry wood tables and stools, string lights and big amber globes, and a library, all under a glass rooftop framed by steel. Cindy's brings classic comfort and culinary invention together over cocktails and large format apothecaries. Open for dinner, cocktails, and weekend brunch.
Numerous people recommended I visit Cindy's Rooftop before I left on my trip to Chicago and boy am I glad I heeded their suggestions. My mom and I sat outside on the terrace in one of the large communal sofas. We sipped on delicious cocktails and shared an order of the roasted cauliflower and burrata. The food is served family style which we didn't realize so between the two of us we couldn't eat every last delicious bite. If you are with a group of four or more the family style is perfect but if you are alone or just a party of two I suggest having the entrées done in a half order or just ordering one entrée. It was the best meal we had in Chicago - not only were the drinks and food absolutely delectable but the service was superb. The staff were extremely friendly, helpful and welcoming. Be prepared for a wait on the weekends, we went on a weekday afternoon so had no wait, but I suggest making a reservation if you can for parties of 4+.
There were so many highlights from my trip to Chicago but this hands down topped them all and this was the one spot I visited in the windy city that I knew I had to share on my blog. If you travel to Chicago - Cindy's Rooftop is not to be missed - you must must MUST go! Put it at the top of your to-do list and relish in the breathe taking views, incredible atmosphere, and delicious sustenance.
taylor ellen. xx