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. 

Upcoming Events

Thursday, November 22nd:
Join us for Thanksgiving dinner, family-style. 
We will be open from 11am-6pm, with the Thanksgiving Menu available all day at $70 per person + mimosa kits for $35 (serves 5).

Tuesday, November 20 +
Wednesday, November 21; 3-6PM:

Pick up a Thanksgiving pie for your gathering – Executive Pastry Chef Jove Hubbard will be offering four flavors to-go ($20 each) in our
Pie on the Fly pop-up shop located on the ground floor of Chicago Athletic Association hotel's 71 E Madison St. entrance. Pie pre-orders can be placed online up to 48 hours in advance of pick-up for the flavor of your choice guaranteed.

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 4PM 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 2PM 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. 



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

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