Enjoy the best rooftop dining Chicago has to offer. 

The jewel in the crown of The Chicago Athletic Association Hotel, Cindy's is our rooftop restaurant and open-air terrace with panoramic views of Millennium Park, the Art Institute, Lake Michigan, and beyond.

Created out of thin air, the aery atmosphere gives contrast to the Association’s history as a men’s club, yet carries an unmistakable look of having always been here. With seasonal freshness reflected in both food and drink, this Chicago restaurant truly offers some of the best cuisine while donning the relaxed ambience of a Great Lakes beach house with a view. Executive Chef Christian Ragano brings family style classic comfort food, bio-dynamic wines and award-winning cocktails with large format apothecaries.


Have dinner in the sky, Chicago.

We accept reservations for lunch, dinner, and weekend brunch.

Lunch, brunch, and dinner reservations are available
for parties of two or more.

The largest reservation that Cindy's can accommodate in our dining room is for 12 guests. Groups of 12+ can be accommodated through a private event. 

Please note we will be closed from January 2nd – January 24th for a refresh of our space.


M-F 11a–1a

Sa 10a–2a

Su 10a-12a


M-F 11a–2p


Nightly 4p–10p


Sa + Su 10a–2p

Limited menu daily
between 2:30p–4p

Upcoming Events

Tuesday, January 2 - Thursday, January 24: CLOSED
We’ll be closed from Tuesday, January 2 - Thursday, January 24 for a little refresh, reopening for lunch on Friday, January 25.
We’ll see you just in time for Restaurant Week.

SOLD OUT | Thursday, January 17: The Craft of Cheese & Charcuterie
Curious about the craft of charcuterie preparation? Join Executive Chef Christian Ragano and Chef de Cuisine Keith Potter for a hands-on cheese and charcuterie tasting and discussion with some of our purveyors.
Tickets are $45.

Friday, January 25 - Friday, February 8: Chicago Restaurant Week
Enjoy our Chicago Restaurant Week lunch menu weekdays only from 11am-2pm between January 25-February 8.
Vegetarian & gluten-free options available; $24 for 3 courses exclusive of beverages, tax, & gratuity.


Sit beside friends, family and colleagues for an unsurpassed experience, only to be found at Cindy’s. Event spaces include our semi-private Lakeview couches, private Library dining room  and full restaurant buyouts. 



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Private Events

From private parties to corporate events, Cindy's is one of Chicago's best event spaces. Our world-renowned view, impeccable service and seasonally fresh menu make our enclosed rooftop one of the best restaurants with private rooms in the city. Party ideas include: company events, networking events, happy hours, team building events, engagement parties, baby showers, birthday parties, wedding party brunches and holiday parties.



Reception MENU