7 Reasons to Visit Chicago Athletic Association

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 1890’s is an architectural treasure with a vast and wild history.  

The facade and interior are finished in a Venetian Gothic style.  The halls and walls echo the rich history of the many movers, shakers, musicians and other colorful characters who put Chicago on the map.  The bold, the bawdy and the bad-asses.


Chicago Athletic Association Stagg Court

The woodwork in this historic Stagg Court is stunning!

Chicago Athletic Association elevators

The elevator walls are made from the re-purposed wood of the tennis courts here.

Chicago Athletic Association swimming pool

The historic swimming pool lies underneath this party room.


Located directly across the street from

Millennium Park, Cloud Gate (a.k.a “The Bean”) and the Art Institute of Chicago, Chicago Athletic Association is one of the hottest spots in town.  I live just a few blocks from here and I have stopped in several times in the last 6 months.  I leave 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.  It is very interesting.


Cherry Circle Room:

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


Cherry Circle Room

Cozy, casual, historic Cherry Circle Room.


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


Cherry Circle Room

Fresh local walleye for lunch!


The closely-spaced tables, booths and large, curvy bar make Cherry Circle Room a warm and welcoming place to dine and imbibe on your own as well as with friends.  I chatted with people sitting next to me very easily and I did not feel the least bit self-conscious dining solo here.

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.  This is so very cool.  I’ll be back to check out some of those dishes.


Game Room:

After lunch and my requisite people-watching at Cherry Circle Room, I wandered through to The Game Room (billiards, bocce ball, foosball, chess, etc) which is also a hopping bar scene.  What an awesome idea!  There is memorabilia on the walls featuring athletes and celebrities from days gone by.  I was there on a very cold and snowy day when all I wanted to do was get out of my apartment, get lost, and have fun for a couple of hours solo.  So, if you’re looking for a fun, clean, grown-up, play-date (with or without cocktails), The Game Room is the place for you!  I like to think of it as an “adult arcade.”


Chicago Athletic Association billiards

Billiards and foosball

Chicago Athletic Association bocce ball

Bocce ball at Chicago Athletic Association


Chicago Athletic Association Game Room

Fancy some billiards, bocce, foosball, chess and more? This is where the cool kids play!


Milk Room:

Next, I passed by Milk Rooman exclusive, 8-seat bar where reservations and tickets are required.  It is called Milk Room as “a wink and a nod” to the Prohibition era when alcohol was outlawed.  Yet, we all know how liquor found its way through trap doors during that time. This is not an inexpensive place, folks!.  I know, it 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 veritable historical liquor lesson in the form of hand-crafted cocktails.  There are spirits here that are seriously old and which cannot be found anywhere else.  So, if you are looking for a really unique Chicago cocktail experience, put this place on your list!  If you are visiting the Milk Room solo, you will be on this tiny cocktail tour with just 7 other people.  Now, this is way better than trying to belly-up to some super loud, crowded bar with sloppy patrons!


Chicago Athletic Association Milk Room

Exclusive 8-seat, reservation only Prohibition-era bar at Chicago Athletic Association.


The Drawing Room:

Personally, I absolutely love The Drawing Room.  It is a wide, open, communal space.  It is beautifully appointed with artwork, plants, large and comfy couches and tables.  There are a few working fireplaces and large windows which look out onto Michigan Avenue and Millennium Park.  You can order, coffee, cocktails, and food in The Drawing Room.  Not interested in spending any money?  No problem.  You can simply curl up with a good book by the fireplace and spend a quiet afternoon, while people-watching or resting your eyes.  You can also bring your laptop and get some work done at one of the large communal tables with reading lamps if you like.  I did all of the above while watching the snow fall through the large, picturesque windows overlooking Michigan Avenue.  This is a great place to hide if you need a break from reality 🙂


The Drawing Room on Michigan Avenue

The Drawing Room Chicago

Drawing Room Chicago

Chicago Athletic Hotel Drawing Room

Chicago Athletic Hotel Drawing Room

Love the cozy fireplaces here!


Cindy’s Rooftop Terrace:

Cindy’s Rooftop Terrace is the premier place to dine at Chicago Athletic Association.  It is a bright, glass-enclosed 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.  It is really fun to grab some friends and order from their list of family-style platters of brunch items. However, they also have enough individual entrees which were perfect for my recent solo visit.  


Chicago Athletic Hotel

Brunch family-style

Chicago Athletic Association Cindy's

Love the glass roof at Cindy’s

Chicago Athletic Association Cindy's brunch

A very chic place to brunch

Chicago Athletic Association Cindy's Roof

The view of Millennium Park and The Bean from Cindy’s terrace

Chicago Athletic Association Cindy's Rooftop

The view from Cindy’s Rooftop looking out toward Lake Michigan

Chicago Athletic Association Cindy's Rooftop Terrace

Cindy’s Rooftop Terrace looking east toward Adler Planetarium

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!

Shake Shack:

On a dining budget?  Chicago Athletic Association’s beautiful lobby is home to the latest outpost of Shake Shack and people are very excited about it.  This New York burger-transplant is delighting wallets of every size here in Chicago.  In the summer, the sidewalk patio is open.  All the better for soaking up the the Michigan Avenue vibe!  I get tempted every time I walk by this place.  Such meaty goodness 🙂


Shake Shack burger

Shake Shack burger

Shake Shack Chicago Athletic Association

Shake Shack at Chicago Athletic Association


Hotel Happenings:

Chicago Athletic Association plays host to some fun musical concerts, exercise classes, art exhibits and storytelling events.  I definitely plan on checking out their events calendar and walk on over there, whenever I feel like I need to get out of my usual routine or rut.  

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

Check out my posts  21 Awesome Chicago Music Venues and  8 Peaceful Places in Chicago to Chill Out.