A friend and I had dinner at Cindy's the other night. This is the new rooftop bar and restaurant at the Chicago Athletic Association Hotel on Michigan Avenue. They only take reservations for tables of four or more (more on this later). We arrived at 6pm and there was a somewhat scary-looking line formed at the elevator in the first floor lobby. The lobby has beautiful floor tiles and is a very nice space. The line actually moved pretty quickly and within 20 minutes we were in the elevator headed up to the restaurant. The elevator is also worth paying attention to. The walls are lined with what I presume is a restored floor from an old CAA gymnasium floor.
The picture on the
website gives a good idea of what the space looks like. There are a few large tables for communal seating, a few picnic-style tables, and bar-style seating. The bar itself is out of the picture and has more seating scattered throughout. On the east side of the space are large glass windows and doors that lead out to another area that overlooks Michigan Avenue and the lake. The weather was beautiful when we were there and these doors were open, so it all felt like one large space. There weren't tables in the outdoor area - it was packed with drinkers. The area where the tables are is covered and so it felt much more like indoor dining than outdoor dining. And for those who particularly dislike loud restaurants, this one was very loud.
Here's the thing about Cindy's: it isn't designed for a party of two. The dishes are large and meant to be shared. On the menu they are called "platters" and billed as serving 3-4 people. With just two people, it's hard to build much of a meal. We had the Great Lakes Fish Fry, which was $34 and enough fried Walleye for three people. Fries were truly excellent. Slaw was tasteless. The side dishes on the menu looked good, but were huge and we didn't want to spring for $16 for a platter of grilled asparagus, for example. But we wanted to sample more dishes and, at our waitresses suggestion, tried the meatballs. They were fine, though not good enough or a large enough portion to justify the $24 price. The stars of our visit were the cocktails. All were inventive, complex, and well made.
The food we had was simple, straightforward, and well executed. This would be a fun place for a party of 4-6 people. You can make a reservation, order a variety of dishes, and experience the restaurant the way I presume it was intended.
Cindy's Rooftop Restaurant
12 S Michigan Ave
Chicago, IL 60603
cindysrooftop.com