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  • Writer's pictureKhushal Benjaram

Cindy's Rooftop: More Than Just Views?

Who doesn’t love a nice skyline sunset? I know I sure do. Cindy’s Rooftop prides itself as being “the best rooftop dining in Chicago,” but does the dining experience measure up to the picturesque views of Millenium Park and the skyline? Read along to find out.



Cindy’s is located on the 13th floor of the Chicago Athletic Association Hotel. Being right on Michigan Avenue, Cindy’s is in the heart of the city and attracts many who want to catch the sunset or meal after a long day of shopping. The restaurant is known throughout the Windy city as being one of the best places to catch the sunset, but pretty views aren’t the only thing this place has to offer!


Defined as a rooftop bar/eatery, Cindy’s offers both dine-in cuisine along with a more laid-back bar area outside. From oysters and burgers to a variety of desserts, there is something for everyone here! Reviews claim that Cindy’s has the perfect blend of good music, food, views, and overall ambiance. Although, the views of Millenium Park and the Chicago skyline do come at a price. The menu items range from $11-30 with drinks averaging around $16. The 4.5/5 star reviews seem to show that this price is worth it! But if you want to save a little coin, you can still enjoy the amazing views! Cindy’s rooftop is free and you can go up there to enjoy the sunset without dining in.


I would definitely recommend stopping by Cindy’s when you’re in Chicago. It is definitely a little bit of a splurge, but I think the food, views, and ambiance are well worth it. For the best experience, I recommend going during the evening around sunset to maximize your Instagrammable opportunities. Due to Covid-19 restrictions, Cindy’s is currently closed to the public, but it's opening up again on April 1st. Masks and all other Covid regulations will still be enforced, but the reopening could be a great way to catch up with friends and family after a couple of tough months. The outdoor area also provides an atmosphere for Covid safe interaction and appropriate social distancing.


So the next time you’re in Chicago and want to treat yourself a little or take some cute Instagram pictures, hit up Cindy’s Rooftop for some delicious food, good service, and even better views! The bar/eatery definitely delivers on its claim as being “the best rooftop dining in Chicago.” Make sure to get a reservation fast if you plan on dining in!


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