Restaurant Reco: Cindy’s Rooftop

Last night I went to a going away dinner for a dear friend who is leaving Chicago for New York at a very popular Chicago restaurant, Cindy’s Rooftop. I am so sad to see her go, but we needed to celebrate her new job and new future ahead with a great meal. Cindy’s is popular for a few reasons: the view, the location, the cocktails, and the food. Basically, it checks all the boxes for an awesome dining experience. The restaurant/bar/rooftop is the top floor of the Chicago Athletic Association, a historic building at 12 S Michigan Avenue, across the street from Millennium Park. The original architecture of the building dates back to the 1890s, and they have put in an enormous effort to upkeep the beauty and charm from the turn of the century.

photo credit: Michigan Ave Magazine

Cindy’s Rooftop appropriately contrasts the classic, bold look-and-feel of the building. It is modern and bright, adorned with large windows, string lights, and natural-colored wood furniture to seat hungry guests. Both their brunch and dinner menus are designed for sharing. Last night was the first time I went for dinner, and I was not disappointed.


Of course, we started with the burrata. If you have been keeping up with my posts, this isn’t the first time I’m writing about an amazing burrata experience, and it won’t be the last. The toasty, charred bread and the acidic pop from the tomatoes balanced out the rich cheese perfect. I was in heaven.

Between the six of us, we ordered two large plates and two sides, which ended up being more than enough food. We were worried about how pricey this place can get, but we all agreed that the price for our meal was nothing crazy, and definitely worth it.

bottom: carbonara | back: pork belly | left: crispy potatoes

My favorite dish of the night was the pork belly. It was served over a huge platter of fried rice, which was full of colorful veggies and rich spices. The pork belly was melt-in-your-mouth tender, and we all agreed we would’ve eaten a whole other platter. The carbonara was also delicious. The fresh pasta was dressed in the classic carbonara fixings (ham/peas) and a creamy sauce (typically made from egg yolk). I gave it the Italian stamp of approval. The crispy potatoes were served with a bacon aioli. I don’t think I have to do it any more justice than typing the words “bacon aioli.”

This was a great dinner dining experience in the Loop, which is sometimes hard to come by. You NEED a reservation to eat here, so call weeks in advanced so you and your closest pals can soak up all that downtown Chicago has to offer.


What is your favorite scenic restaurant?

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