22 Hours at The Chicago Athletic Association Hotel: Staycation Birthday Edition

My wife Julie and I absolutely love the transcendent power of a carefully-curated hotel like the Chicago Athletic Association.  Established in 1890, it was once an athletic, business and social club for men only that has now been reimagined into a place that feels both familiar and foreign in the city where we live.

The smell of leather and worn worn  remind me why I’ve always dreamt of designing and owning boutique hotel. The Chicago Athletic Association evokes a paradigm of time that feels like yesteryear…. or perhaps how things should be in our future.

As part of my Birthday spoiling this year, Julie booked a corner suite in the Chicago Athletic Association hotel which was also host to one my most favorite nerdy offerings, The Chicago Humanities Festival. It was the perfect excuse to book a room, see a lecture or two, and nosh/imbibe at some of the hottest places in Chicago.

And it’s male-only roots seemed apropos as a destination for our next SheShe staycation.

Chicago Athletic Association

2pm Check In: The Drawing Room

Check in is on 2nd floor, which was previously the men’s Drawing Room flanked by roaring fireplaces and a staggering amount of patrons drinking cocktails and wearing bow ties. Considering it was only 2pm, we were delighted to hear our room was ready for our Saturday night stay.

We snagged a suite on the 4th floor which had great views of Michigan avenue and even “the bean” if you craned your neck. The room was appointed with amazing details like a pommel-horse bench at the end of the king bed (great for late-night, alcohol-induced gymnastics), a spacious bathroom with double sinks and C.O. Bigelow products, a well-stocked mini bar and a classy sitting room area.

2:30pm Chicago Humanities Festival

One of the things I love about our city is that there are things like the Chicago Humanities Festival to keep you cultured and current. The spring series this past weekend focused on Style and brought together writers, photographers and fashion designers with inspiring stories to share. Our first session was at Stagg Court in The Chicago Athletic Association, which was the old shuffleboard court. It was the perfect backdrop to hear iconic fashion designer Isabel Toledo and her husband Ruben discuss the marriage of fashion and style.

4:00pm: Game Room

On a rainy day in Chicago, your first time in The Chicago Athletic Association’s Game Room might be a bit overwhelming as it’s likely filled with people playing bocce, shuffleboard or chess and you aren’t sure how to get in on the action. Look for the woman with the clipboard and put your name down for your game of choice (all free). Be warned, the wait for shuffleboard was two hours, so find a nook to order drinks and the Fried Pickle Pops.

6:00pm: Cocktails at Cindy’s Rooftop

Cindy’s Rooftop is one of the newest spots filled with PYTs in the city. It boasts an outdoor terrace with fire pits and killer views of Millennium Park and the Modern Wing of the Art Institute. The general public cues up for Cindy’s on the ground floor of the Chicago Athletic Association, but if you are staying at the hotel, take the back set of elevators up to floor 13 and follow the noise to the last door marked “private” and you can let yourself in with no line, no waiting.

7:00pm: Taxi to dinner at Momotaro

If you know anything about Julie and me, we love everything Asian… including the Japanese fusion spot, Momotaro. The sushi is good, but if you want to see what sets this place apart, go for the inventive “robata” options on the front side of the menu instead. Standouts include the tartare, Chawan Mushi (king crab dip), Short Rib Motoboro skewers and Washugyu skewers.

9:00pm Drinks in the Milk Room (or Drawing Room)

Chicago Athletic Association Drawing Room
The Drawing Room at night.

Named after the Prohibition-era speakeasy that was part of the Chicago Athletic Association where members would go to drink “milk”, the current day Milk Room is a artful coffee bar by day and an exclusive, ticket-only cocktail affair by night. For $50 per person you can reserve a seat and then that money goes towards your cocktails. But if you’re like us and don’t appreciate single malts, you can just drink wine and people watch in the Drawing Room which is pretty good too.

11:00pm Aforementioned Alcohol-Induced Pommel Horse Gymnastics

No further comments.

9:00am Coffee at the Milk Room or Room Service

The rooms don’t have coffee makers, but they did come with tokens good for a specialty coffee of your choice down at the Milk Bar where they brew Metropolis beans. Or, if you are like us who love nothing more than reveling in the reality that you don’t have to get up and walk the dogs, order in a pot of coffee and enjoy the last drop of that vacation feeling.

10:00am Brunch at Cindy’s

Since tables for brunch are at a premium, do not take the hotel guest elevator to the back door of Cindy’s even if you’re staying there. Take the elevator down to the first floor where, if you are a hotel guest, you will bypass the rest of the line and be whisked up to brunch on the roof. The food is primarily family style which was a bit odd if you only have a group of two, but Julie and I managed to kill the Chilaquiles which were portioned for 3-4. They do take reservations for four or more, so plan ahead on a sunny Saturday and reserve your spot.

12:00 Noon Check out

The feeling of being on vacation in your own city is one of our favorite SheShe things we love most. Pack a light overnight bag, get someone to watch the dogs, and let yourself spend money on a fabulous mini getaway. Then hop in a cab and you’re home in 20 minutes. No canceled flights, no excessive laundry and nothing but falling in love with each other and this city all over again.


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