In 2007, a historic private men’s social club closed its doors for good, but the grand Chicago Athletic Association building could not be ignored. Eight years later, a newly polished Michigan Avenue boutique hotel opened in its place for all to enjoy. And enjoy it you will.
As you walk through the front doors of the Chicago Athletic Association Hotel, you’re stepping into more than 100 years of Chicago history. The second floor lobby is a Gothic work of art. Thanks to a glamorous and thoughtful renovation, you can easily imagine what it was like to enjoy whiskey, a cigar, and some friendly conversation here when it first opened in 1893.
There are 241 rooms in this fully restored Venetian Gothic building. Each room is impeccably decorated, with no detail overlooked. The masculine prep feel is a nod to the building’s past life, with dark wood, soft leather, and iron details coming together to form clean lines and cozy vibes. But don’t get too comfortable. The rooftop is where you’ll want to head directly after settling in.
Cindy’s open-air terrace overlooks Lake Michigan and Millennium Park, and thanks to a couple strategically placed outdoor fire pits, you can enjoy the astounding city views even when the weather isn’t perfect. The sunlight-filled restaurant is great for large groups (the menu is filled with oversized, shareable plates from brunch to dessert), but parties of two will have no problem finding cozy high-top seating. However, it will be hard to stop yourself at only one cocktail. Even locals head to Cindy’s to observe the top notch bartenders in action. But this modern addition is only a brief stop during your tour of the Chicago Athletic Association Hotel. Next, you’ll want to step back in time to the second floor.
Once you’ve worked up an appetite, head way past the lobby to the Cherry Circle Room for dinner. The moody space with a country club feel is a re-imagined concept of the original iconic restaurant that served Chicagoans for decades. As you browse the menu, you’re perusing some of the same dishes and drinks that were served here as far back as the 1890s. Save some energy for post-dinner activities. You can get in on a round of indoor bocce ball, billiards, or shuffleboard in the game room just outside the restaurant. If you’re lucky, as you head back to your room, you might stumble upon the Milk Room, a former speakeasy hidden between this space and the lobby.
Time travel is the name of the game here at the Chicago Athletic Association Hotel. Even the elevators are lined with memories of the landmark’s storied past. (Are those old fencing courts lining the walls? Yes.) You’ll be transported to a different decade and come to appreciate the Chicago of yesterday and today. Which is better? Only time will tell.