All Are Welcome: A Visual Tour of The Chicago Athletic Association Hotel đŸ©

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Chicago Athletic Association Hotel

Johnny Weissmuller was an actor, five-time Olympic gold medalist, and the best competitive swimmer of the 20th century. He was also a member of Chicago Athletic Association. He’s honored here on my key-card.

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The Chicago Athletic Association is a museum. Not intentionally, maybe, but nonetheless it is a stoic witness to a world now dead.  A world sinking in a tide of economic uncertainty and hysterical fear of integration. In fact, being both black and female,  I was never meant to see the inside of the CAA. Its doors were opened shortly ahead of The Chicago World’s Fair in 1893 as a men’s only athletic club. Its members were chosen by a vote in which only existing members could participate. Inside its walls were the most celebrated men of business and sports: Olympic swimmers, pro footballers, and William Wrigley who adopted the club’s logo for his pet project, the Chicago Cubs.

Chicago Athletic Association Hotel

Look familiar?

With such an impressive pedigree, I expected a cold aloofness inside. What I found was just the opposite.

I should back up here and say that I’ve visited the CAA many times, usually for Cindy’s. Cindy’s bar and restaurant is arguably the current “it girl” of Chicago’s rooftop scene. To get there you enter on the main floor and take an exclusive elevator to the top, blindly passing levels of restored woodwork, marble, light and art installations. I wanted to know the landmark intimately, beyond just Cindy’s. So, I decided to live there.

Well, for a day. In one of their bedrooms. Basically, I stayed there for a night.

This week, Chicagoings will review this hotel in all of its parts, including what some are calling the best and most exclusive bar in the city, Milk Room. Stay tuned. In the meantime, here’s a taste of what’s to come.

A Visual Tour of the Chicago Athletic Association

Lobby and Entrance

It’s all in the details.

Chicago Athletic Association Hotel

One of the most Instagrammed floors in Chicago: The mosaic tiles of the lobby floor.

Chicago Athletic Association Tour Chicagoings

Get it? 😝

Chicago Athletic Association Tour Chicagoings

Look at me! I’m standing next to some old mailboxes. I’m so crazy you guys.

Chicago Athletic Association Hotel

Chicago Athletic Association Hotel

Chicago Athletic Association Chicagoings (7)

Developers originally intended to keep and restore the pool, but with its right-at-the-entrance location, it made more sense to convert it into a chic event space.

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Chicago Athletic Association Hotel

Chicago Athletic Association Hotel

The Rooms

Something old, something new.

Chicago Athletic Association Hotel

The details recall to mind CAA’s proud athletic heritage. A pommel horse is converted into a bench, a gym ladder into a storage wall, even the bed reminds me of monkey bars.

Chicago Athletic Association Hotel

Chicago Athletic Association Hotel

Chicago Athletic Association Interior (4)

Chicago Athletic Association Hotel

Chicago Athletic Association Hotel

Guests are provided with two complementary coffee tokens, redeemable at the Milk Room each morning.

Chicago Athletic Association Hotel

Chicago Athletic Association Hotel

Bars are stocked with spirits from local distilleries.

Chicago Athletic Association Hotel

Chicago Athletic Association Hotel

Chicago Athletic Association Chicagoings (5)

chicago millennium park

The view isn’t bad.

Game Room

Free and open to the public.

Chicago Athletic Association Game Room

Chicago Athletic Association Game Room

Chicago Athletic Association Hotel

Open from 11 a.m. till 1 a.m, the Game Room is the perfect place to gas up for an all-nighter. It’s been a pool hall since the old days but now additionally holds a few Foosball tables, a Bocce Court, and board games.  The burgers are good and the drinks exceptional.

Milk Room

This small, eight seat micro bar resembles a Gothic torture chamber. I assume it was once reserved for top-secret hazings and rituals. I’m told it’s always been just a bar. Yea, sure.

Land and Sea Dept controls the beverage program here. You know them from such hits as Longman & Eagle and Parsons Chicken and Fish but you’ve never seen them like this. Ever drop $200 on a bar bill? Crack open that wallet and come here to drink what your great-grandfather used to.

Grant Achatz

Chicago Athletic Association Milk Room

Drawing Room

Chicago Athletic Association

Chicago Athletic Association Drawing Room

Chicago Athletic Association Personal (2)

Idea: People are the worst. Avoid them by having lunch solo in the CAA’s drawing room. Bring your laptop, stay longer than you should, finish the group project on your own like everyone knew you would anyway.

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Cherry Circle Room

Illuminati much?

Seriously, if you love mason imagery, conspiracy theories, and good food, or either of those things exclusively, this is the place for you. The dining here’s a little more adult than Cindy’s but doesn’t sacrifice imagination for tradition. Some key items date all the way back to the club’s original menu. I recommend the Tuna Crudo, French Onion Soup, and Steamed Mussels.


Living up to the hype.

Cindy’s for me is an old standby. When I have no idea where to go for brunch or drinks, I go here. That’s because the menu and service is reliable. The drinks, while not made with liquors as rare as those of Milk Room, I’d argue are some of the best you’ll find in the Loop. But brunch is where the rooftop really shines.

cindy's chicago

All photos by Kari Herrera — unless I’m in them. In that case, they were taken by Alberto Herrera.

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Kari Herrera is the creator of, Chicago’s indie city guide and blog. She often writes about the city’s points-of-interest as experienced by a local. She is a Social Media Marketing Manager and freelance writer. When she’s not working, Kari donates much of her time to the education of French-speaking immigrants in Chicago.

  • Those photos are amazing. Adding this to my staycation lists!

  • Honor

    Lol I love this article and the photos! I’ve been here only once and enjoyed every bit of it. Your article makes me want to hurry back😀

  • SimplyC

    I want to surprise my hubby with a close to home get-away and this looks like the perfect ‘Mancave’ spot. Thanks for the info!!!👍🏿

    • You WILL not be disappointed! Let me know how it goes. Enjoy and thanks for reading!!

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