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. 


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

Friday, December 14th:
Our last lunch seating will be at 1:30PM + we will not re-open to the public for dinner service.

Thursday, December 20th:
Our last lunch seating will be at 1:00PM + we will re-open to the public at 9:30PM for dinner service.

Friday, December 21st-Sunday, December 23rd, 3-6PM: Christmas Cookie Pop-Up
First Floor of Chicago Athletic Association Hotel (71 E. Madison Street Entrance)
Executive Pastry Chef Jove Hubbard brings back a holiday favorite with his Christmas Cookie Pop-Up,
returning this year for a limited time, available for pre-order and pick-up.

Saturday, December 29 - Tuesday, January 1: Brunch4Days
Enjoy four days of extended brunch service New Year's Eve weekend – served daily in lieu of lunch from opening through 2PM Saturday-Monday,
and until 4:00PM on Tuesday. 
**Please note our regular dinner hours and menu apply Saturday and Sunday only.**

Monday, December 31st:
We will be closed for a private event this New Year's Eve – our last seating will at 2:00PM and we will not reopen to the public that evening. We encourage you to ring in 2019 in Chicago Athletic Association hotel's Game Room, Cherry Circle Room, Milk Room, or Drawing Room, all located on the second floor.


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. 


General Info

facebook: Cindy's Rooftop     instagram: @cindysrooftop.    twitter: @cindysrooftop

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