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.
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.
One of the most Instagrammed floors in Chicago: The mosaic tiles of the lobby floor.
Get it? 😝
Look at me! I’m standing next to some old mailboxes. I’m so crazy you guys.
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.
Something old, something new.
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.
Guests are provided with two complementary coffee tokens, redeemable at the Milk Room each morning.
Bars are stocked with spirits from local distilleries.
Free and open to the public.
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.
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.
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.
Cherry Circle Room
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.
All photos by Kari Herrera — unless I’m in them. In that case, they were taken by Alberto Herrera.