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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, July 27th 7:00-10:00AM – Field Trip to Green City Market & Private Breakfast at Cindy’s
Join us on a Field Trip from the Chicago Athletic Association hotel! We’ll be getting a private tour & taste of the season with Green City Market, let by our own Executive Chef Christian Ragano.

Your itinerary includes:
Private Breakfast at Cindy’s
Did you know Cindy’s was Green City Market’s highest-volume supporter in 2018?
Enjoy a family-style breakfast with market-fresh ingredients & get to know our culinary team.

Green City Market Tour
After breakfast, we’ll head to Lincoln Park to learn what makes this market stand out.
Longtime purveyors will share their stories, from successes to climate change challenges.

Independent Exploration
Keep tasting & exploring! We’ll leave you equipped with a schedule of market activities to enjoy on your own.

Tickets: $50

Sunday, July 28th 11:00AM & 1:30PM – Cocktail Workshop: Herbs, Leaves, & Flowers
Summer is here, and so are bright, refreshing drinks to complement the season. In our fourth installation of the Cocktail Workshop Series, spend the afternoon with Cindy’s Beverage Manager David Mor, and learn hands-on how to create quenching summer cocktails featuring herbs, leaves, and flowers. With gardens blooming summer-round, David will highlight ways to incorporate ingredients like mint, thyme, sage, and edible flowers into a range of cocktails – from classic Mojitos and Southsides, to modern recipes made daily at Cindy’s.

This 90-minute workshop includes recipes and items to recreate cocktails at home, plus light bites during class. A 11:00AM and 1:30PM session is offered.

Tickets: $50

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:
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. 


Questions? Email us at

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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



Questions? Email us at