In addition to Chicago Athletic Association's luxurious accommodations, the hotel is home to seven of the city's best-loved dining establishments. The space that club members once used to recharge has now transformed into a hub for hotel guests and locals seeking spirited hospitality and artful cuisine. Kaleena Bliss, the Executive Chef at Chicago Athletic Association, brings her expertise as a Chopped Grand Champion to lead both the banquet program and the kitchen at Cindy's.

Cindy's is our all-seasoned rooftop restaurant atop the hotel with sweeping views of Millennium Park and Lake Michigan. Serving local cuisine, cocktails, and wines with Chopped Grand Champion Executive Chef Kaleena Bliss leading the culinary team.

Monday – Thursday: 11am to 11pm

Friday: 11am to 12am

Saturday: 10am to 12am

Sunday: 10am to 11pm

Cherry Circle Room
James Beard award-winning Cherry Circle Room melds the building's historic original features with modern design elements. The refined menu features throwback cocktails and tableside presentations of the finest meats.

Breakfast: Monday - Friday: 7am to 11am

Dinner: Monday - Saturday: 5pm to 11pm; Sunday: 5pm to 9pm

Brunch: Saturday & Sunday: 7am to 2pm

Game Room
The original billiards room, Game Room, transforms into a lively bar and playground with a cocktail culture, classic suds and grub, and games like pop-a-shot, skeeball, billiards, shuffleboard, chess, and checkers.

Monday – Thursday: 11am to 11pm

Friday: 11am to 2am

Saturday: 10am to 2am

Sunday: 10am to 9pm

Drawing Room
Adorned with three fireplaces, the Drawing Room serves rustic yet refined menu with takes on regional classics. It's perfect for morning emails, a good book, or a strong cocktail.

Monday – Thursday: 11:00am to 11:00pm

Friday and Saturday: 11:00am to 12:00am

Sunday: 11:00am to 9:00pm

Milk Room
Milk Room, a former speakeasy, is an eight-seat microbar that specializes in rare vintage spirits and curated whiskies. The spirit-forward cocktail menu creates a historical drinking experience with epic stories.

Milk Room Café:

Monday – Sunday: 7:00am to 1:00pm

Milk Room:

Sunday – Tuesday: 5:00pm to 9:00pm 

Wednesday – Saturday: 5:00pm to 11:00pm

Shake Shack
Chow down on Shake Shack’s mouth-watering burgers, crinkle cuts, and frozen custard shakes surrounded by stained glass, soaring ceilings and marble staircases in our downtown Chicago hotel.

11am - 9pm daily

Fairgrounds Coffee + Tea
Cold brews and sparkling teas are served on tap at Fairgrounds. You'll also find a variety of artisanal beverages, kombuchas, and matcha whipped to order.

Monday – Friday: 7am to 3pm

Saturday & Sunday: 7am to 5pm

Topgolf Swing Suite
Practice your swing at Chicago’s first Topgolf Swing Suite, located on the ground floor of our downtown Chicago hotel. Play at two of the most advanced indoor golf simulator bays available. Fuel up for play with food-and-beverage service provided by Chicago-based restaurant group Land and Sea Dept. FOR GENERAL INQUIRIES info@lsdatcaa.com

Monday – Saturday: 11:00am to 11:00pm

Sunday: 11:00am to 9:00pm

In-Room Dining
In-room dining is available daily, including selections from Cindy's and Shake Shack, the only hotel in the world where guests can order Shake Shack directly to your guest room.


Monday – Friday: 7am to 10am,

Saturday – Sunday: 7am to 11am

Lunch/Dinner via Shake Shack:

Monday – Sunday: 11am to 8:30pm

Dinner via Cindy's:

Wednesday – Sunday: 5pm to 10pm