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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

Book your Cindy's Rooftop reservation on Resy

Upcoming Events

Saturday, March 16 & Sunday, March 17: St. Patrick’s Day Brunch
This St. Patrick’s Day weekend, we will offer a Cast Iron Irish Breakfast and Wagyu Pastrami
Reuben in addition to our regular brunch menu. Available during brunch service hours 10AM-2PM only.

Wednesday, March 20 at 6:00PM: Lakehouse Series Dinner: Wild Game Wild Cider
Join us for an intimate dinner exploring wild flavors inspired by untamed nature,
featuring tastes of forest game & sea shore paired with rare varietals of aged ciders.
A collaboration between our own Chef de Cuisine Keith Potter and Pastry Chef Jove Hubbard
alongside Chef James Rigato of Detroit’s Mabel Grey and Ryan James Burk of Angry Orchard.
Tickets: $165 (inclusive of tax + gratuity)
View the menu here.

Tuesday, April 2nd at 1:30PM-CLOSE: Private Event
We will be closed to the public for dinner service; our last lunch seating will be at 1:30 p.m.


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