Chicago Athletic Association: Awesome Hang!

Chicago Athletic Association was restored last year into a wonderful hotel, dining destination and playground for the city’s visitors and residents alike.  This turn-of-the-century building from the 1800s is an architectural treasure with a vast and wild history.  


The Drawing Room at Chicago Athletic Association

Pull up a rocking chair or a winged-back chair in The Drawing Room!


Located directly across the street from Millennium Park and the Art Institute of Chicago, you can reach Chicago Athletic Association by taking the CTA #3 King Drive and CTA #4 Cottage Grove buses directly there.  If you’re riding the ‘L’, the CTA Orange, Brown, Green, Purple and Pink Lines all stop within one block of the hotel. You can exit at the Washington/Wabash stop.



Adams/Wabash 'L' stop near Shake Shack


I live a few blocks from Chicago Athletic Association and I have stopped in a few times.  I leave there always wanting more.  However you decide to spend your time here, I highly suggest you take the FREE 45-minute tour of this historic building.  Very interesting.  However, today’s blog is about eating and drinking at this awesome place.  

During Chicago Restaurant Week, I had lunch at Cherry Circle Room which is an interestingly shaped room with a very private, club-like feel.  I am certain that many important business deals and clandestine affairs went down in this space.  But I digress.  Here’s how my lunch went down:



Cherry Circle Room

Cherry Circle Room is a cozy, clandestine spot.



I ordered this lovely walleye pike and shellfish dish with a fennel and saffron broth.  It was really light and flavorful.



Cherry Circle Room menu

Cherry Circle Room has menu items from decades and decades ago!


An interesting thing about the menu at Cherry Circle room is that they feature historic menu items from when the Chicago Athletic Association first opened.  Very cool.  I’ll be back to check some of those out.



Cherry Circle Room at Chicago Athletic Association

Loved this local walleye pike and shellfish dish with saffron and fennel sauce!


After lunch and my requisite people-watching, I wandered through “The Game Room” which is also a hopping bar scene.  Billiards, foosball, bocce or chess, anyone?!



Billiards at Chicago Athletic Association

Billiards and booze at The Game Room

Chicago Athletic Association bocce

Who likes bocce ball?!

The Game Room Athletic Association

The Game Room/Bar at Chicago Athletic Association


Next, I passed by the super cool, Milk Rooman exclusive, 8-seat bar, where reservations and tickets are required.  This is not an inexpensive place, folks!.  Sounds a bit pretentious but I don’t think there is another bar like this anywhere else in Chicago.  You arrive at your designated reservation time and the bartender delights you with a historical liquor lesson in the form of pricey, hand-crafted cocktails.  There are spirits here that are seriously old and which cannot be found anywhere else.  Who would like to treat me to this unique experience? Anyone?  Anyone? 


Milk Room at Chicago Athletic Association

The 8-seat, reservation/ticket-only Milk Room


Personally, I absolutely love “The Drawing Room.”  It is a wide, open, communal space.  It’s beautifully appointed with artwork, plants, comfy couches, and tables.  



The Drawing Room at Chicago Athletic Hotel

Comfy couches and stunning woodwork!


There are a few working fireplaces and large windows which look out onto Michigan Avenue and Millennium Park.  



Chicago Athletic Association fireplaces

Grab a book and curl up by one of the fireplaces~


Chicago Athletic Association


You can order, coffee, cocktails, and food in The Drawing Room.  Not interested in spending any money?  No problem.  You can curl up with a good book by the fireplace and spend a quiet afternoon while people-watching.  Bring your laptop and get some work done, if you like.  



Chicago Athletic Association Michigan Avenue



Last but definitely not least, Cindy’s Rooftop Terrace is the premier place to dine at Chicago Athletic Association.  It is a bright, sunny space with an astoundingly beautiful view of Millennium Park and the Chicago lakefront.  They open weekdays at 3 pm and weekends for brunch at 10 am.  Individual entrees are available.  However, I suggest you grab some friends and order from their list of family-style platters of brunch items.



Cindy's Rooftop brunch

Don’t be stingy! Share your eggs and pancakes 🙂

Brunch at Cindy's Rooftop in Chicago

Family-style brunch platters at Cindy’s is fabulous fun.

Cindy's at Chicago Athletic Association

Cindy’s Rooftop Terrace overlooking Lake Michigan and Millennium Park

Cindy's at Chicago Athletic Association

View of Millennium Park from Cindy’s Rooftop Terrace

Cindy's Rooftop Terrace

Looking at The Adler Planetarium from Cindy’s Rooftop Terrace


Pro tip:  Cindy’s Rooftop Terrace is a perfect spot to sip cocktails and watch the Navy Pier fireworks on Wednesdays and Saturday nights during the summer.  Make a reservation, though!


Cindy's Rooftop in Chicago

Cindy’s Rooftop is one of the hottest dining destinations in Chicago.


Chicago Athletic Association is located at 12 S. Michigan Avenue.  Click here for more information.

In keeping with the spirit of Feeding Off The Rails, I encourage you to leave your car at home and take the CTA trains or buses to Chicago Athletic Association.  Save on gas. Avoid traffic, road rage and parking.  Reduce pollution. Don’t drink and drive! 

Thirsty for more?  Check out the 11 Chicago Bars You Must Absolutely Visit.