Dining Out: Cindy's

After visiting the Bean in Millennium Park I was floating. It was such a magical piece of work and I found myself truly moved and inspired by the experience. Little did I know my Chicago hostess would take that feeling to the next level by walking us over to Cindy's across the street. 

Cindy's is a rooftop bar located in the Chicago Atheltic Association Hotel. The doormen are dressed like ball boys at a tennis tournament. The lobby is home to Shake Shack and the hostess stand for Cindy's. We put our name in and they said it would likely be a 25 minute wait. 

40 minutes later we finally go a text to head back to the hostess stand. From there, the host pointed us toward a second line, this one for the eleavtors. We waited another 10 minutes or so and then finally headed up to the 13th floor. 

When we got off the elevator I was worried the place would be completely packed. To my surprise, there was plenty of room for us and we were able to find a spot at the bar very easily. 

The bar at Cindy's is decorated with rows and rows of orange jars, punctuated by four rose gold pineapples. Yes, I thought about trying to steal one. 

Cindy's Cindy's

We took a quick look at the drink menu so we wouldn't lose our chance to order.


The cocktail section is called "High Noon Potions & Elixirs." How very "Alice in Wonderland."


My friend went with a drink called the Grey Garden which is Ketel One, dolin blanc, créme de violette, emperor's jasmine pearl tea and lemon. I love that it comes garnished with a flower. I kept it simple and went with a glass of rosé. 


We took our drinks and headed through the dining room to the roof deck. I love the enormous floor to ceiling windows and the skylight in the dining room. It makes the enter space feel like it's outdoors. 


When we stepped out onto the terrace my jaw dropped. We had a completely unobstructed view of all of Millennium Park down below. To the right, you could see the brightly colored umbrellas of Park Grill, the Bean and the Jay Pritzker Pavilion. The Pritzker Pavilion was designed by world famous architect Frank Gehry and is a popular location for outdoor concerts and movies. 

Cindy's Cindy's

Straight ahead, we could see all the way to Lake Michigan. 


To the left, you could see Crown Fountain down below. The fountain was designed by Jaume Plensa and consists of a black granite reflecting pool and two glass brick towers. The towers are 50 feet tall and use LED lights to display digital videos. Every few minutes the display shows two faces (on each tower) and water comes cascading out of their mouths like a waterfall. The day we went it was super hot and kids were running through the water with glee. 


You can also see to the right (of this photo above) Chicago's Art Institute. 

I could not get over the beauty of Cindy's, inside and out. The restaurant space is light, airy and sophisticated. I love the whimsy of the menu design and the picture perfect composition of the cocktails. Though we didn't have any food while we were there, Cindy's is open for lunch, dinner and brunch. And it goes without saying that the view is spectacular. 

If you are planning a trip to Chicago or even if you already live there, the next time you visit the Bean, a drink afterward at Cindy's is an absolute must. 


Kristen Fenton's picture

those views! what an incredible place.

Molly's picture

This was one of those instances where the photos could never do it justice. It really is an incredible place for a first time visitor.

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Molly Galler

Welcome to Pop.Bop.Shop. My name is Molly. I’m a foodie, fashionista, pop culture addict and serious travel junkie. I’m a lifelong Bostonian obsessed with frozen confections, outdoor patios, Mindy Kaling, reality television, awards shows, tropical vacations, snail mail and my birthday.

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