The Chicago Athletic Association Hotel: A Historical City Gem

The Chicago Athletic Association Hotel

Ever since I got word that the Chicago Athletic Association was reopening as a hotel, I’ve patiently waited for an opportunity to pack up my Vera Bradley weekender and check it out. Intrigued by the rich history of the space, I finally made a point to check lodging at the hotel off of my bucket list – and let me just say – it will not be my last visit.

The Chicago Athletic Association opened up in the 1890’s following the Chicago World’s Fair as an exclusive club for some of Chicago’s most elite men. Members included Marshall Field, William Wrigley, and Cyrus McCormick – just to name a few. The building itself is nothing short of architectural magnificence. Designed by renowned architect, Henry Ives Cobb, the Chicago Landmark boasts exquisite detail – featuring a Venetian-Gothic facade (2015). Situated directly across from Millennium Park, sandwiched between Monroe and Madison, the Chicago Athletic Association sits in the heart of Chicago’s loop, steps away from many of the city’s most sought-out attractions.

Every detail of the hotel was thoughtfully designed to replicate the athletic club it functioned as from the late 1890’s through 2007. Below you’ll find a breakdown of some of my favorite features of the Chicago Athletic Association Hotel.

The Rooms:

The detail in the guest rooms is surely something to appreciate. From the boxing-inspired bath robes & C.O. Bigelow Barber products to the clever “Do Not Disturb” signs – every inch of the guest rooms was well thought out and designed with the historical club in mind.

Chicago Athletic Association Hotel Rooms

Chicago Athletic Association Hotel Boxing bath robes

Chicago Athletic Association Hotel Club Room Bathrooms

Chicago Athletic Association C.O. Bigelow Bath products

Chicago Athletic Association Do Not Disturb Sign

Game Room:

This space was designed to reflect the game space that was enjoyed by the club’s members. Filled with everything from billiards to chess tables, this is the go-to spot to take part in some games while you enjoy the tasty bites and sips of the playful space.

The Cherry Circle Room:

Tucked away in the back corner of the hotel’s Game Room bar, you’ll find the cozy Cherry Circle Room quaintly situated behind secretive double doors. This space was carefully designed to mimic the restaurant that the CAA members dined in back in the day.

The room features a full menu of delectable eats, accompanied by a selection of tasty libations that are whipped up by skilled, knowledgable bartenders. The Cherry Circle Room is the perfect space to escape the hustle and bustle of the crowded common areas and enjoy a low key atmosphere, ideal for making conversation.

If you’re having trouble finding it, look for the Cherry Circle Room emblem lit up to the left of the Game Room’s bar.

Chicago Athletic Association Hotel Cherry Circle Room Cocktails


A popular spot to grab a cocktail for both Chicago locals and hotel guests, Cindy’s is a bar situated at the very top of the hotel. Featuring breathtaking views and handcrafted cocktails, it’s a trendy spot to grab a tasty sip and take in the beauty of the city.

Drinks at Cindy's Rooftop Bar at the Chicago Athletic Association Hotel

Milk Bar:

Coffee bar by day, exclusive hidden bar by night – Milk Bar is tucked away between the hotel’s Drawing and Game Rooms. The nightly 8-seat bar, features elite liquors from all around the world. I unfortunately did not get to experience Milk Bar at night, in all of it’s prestigious glory, but I did pick up a morning coffee with my handy coffee token. Be sure to plan ahead if you want to visit this space at night – tickets are required.

Shake Shack:

CAA is currently the only hotel in the world boasting Shake Shack not only in its lobby, but on its room service menu. Yes, you heard that correctly, you don’t even have to leave the comfort of your club room to enjoy the popular chain’s grub. Simply dial for room service and patiently wait in your boxing-inspired robe until you hear a knock at the door.

The Chicago Athletic Association Logo:

With William Wrigley as a former member of the CAA, chances are it’s no coincidence that the logo is quite similar to that of our very own Chicago Cubs baseball team. In addition to the association’s logo, below are some other shots I captured of the various details present in the hotel.

Chicago Athletic Association Logo

Chicago Athletic Association Hotel

Chicago Athletic Association Hotel

Chicago Athletic Association Hotel

All in all, the Chicago Athletic Association is one of my favorite hotels I’ve ever had the pleasure to stay at. From the historical elements of the hotel to the vast amount of amenities housed under one chic rooftop bar, this is a wonderful place to stay for both city-dwellers and tourists alike.


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