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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

Wednesday, June 26th: CLOSED for a Private Event
We will be closed for a private event during dinner service this evening. Our last lunch seating will be 1:45PM, and we will not reopen to the public tonight.

Tuesday, May 21st – Monday, September 9th: Terrace Takeover Series
Join us all summer long as we welcome some of our favorite Chicago bartenders for a series of terrace bar takeovers, kicking off May 20th ✨🍸✨ Take in our view as you taste your way through a one-night-only collaborative cocktail menu between 7-10PM on select dates, available on the outdoor terrace alongside our own frozen and draft cocktails.
View the full lineup of takeovers:
Tuesday, May 21st: Liz Pearce; Aba Restaurant + The Drifter Chicago
Monday, May 27th: Sarah Schmitt; RHINE HALL
Monday, June 10th: Rich Beltzer; Bad Hunter
Monday, June 17th: Joe Briglio; Blind Barber
Sunday, June 23rd: Jessica Lambert; Beam Suntory [Pride Night]
Monday, July 1st: Carley Gaskin; Hospitality 201
Sunday, July 7th: Luke DeYoung; Scofflaw
Monday, July 15th: Marissa Huth; Hotaling & Co.
Monday, July 29th: Brandon Thrash; Bad Hunter
Monday, August 5th: Kyle Smith, Tyler Hartshorn, Eric Simmons; H Bar
Sunday, August 11th: Justin Doggett; Breaking Black
Sunday, August 18th: Greg Buttera; Maker's Mark
Tuesday, August 27th: Stephanie Andrews; Billy Sunday
Monday, September 9th: Miranda Breedlove; Good Fortune


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. 


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