Chicago Athletic Association Hotel: Drawing Room
Credit: Courtesy Chicago Athletic Association Hotel

When seasoned travelers are told that a hotel promises an “authentic” experience, the visceral response is an eye roll. Authenticity is a vibe, not an adjective that can be blithely assigned to a space. But this type of emotional nirvana—the warm glow of intuitively connecting with a setting—can be earned through strong design and honest storytelling. And the new Chicago Athletic Association Hotel is authentic.

Originally a historic, turn-of-the-century private gentleman’s sporting club, it’s been reimagined as boutique hotel, and the property reads clubby and cool, a seamless fusion of old-school elegance folded into a modern, come-one, come-all aesthetic (doubles from $369). Perky millennials at reception (beards and partially shaved heads are part of the uniform, it seems) invoke a hospitable hipster tone that ricochets throughout the property.

If you play it right, 24 hours at the CAA can feel like you have conquered several hot spots without setting foot off the property. Before it gets dark, head up to Cindy’s on the 13th floor. Robin Standefer and Stephen Alesch, of Roman and Williams Building and Interiors, designed Cindy’s, The Game Room, and the hotel's guest rooms. The sweeping vistas from the Lake House-themed bar and eatery are jaw-dropping. But it’s the spirited “spirit guide” that supplies the rooftop boîte with wow factor. Nandini Khaund was part of the team that won a James Beard Award for Outstanding Cocktail Program at the Violet Hour, and is the high priestess of cocktails who charmingly works the room, dispensing the type of esoteric factoids that make you want to order every elixir on the roster.

Chicago Athletic Association Hotel: Guest Room
Credit: Courtesy Chicago Athletic Association Hotel

The property’s gaming heritage is illuminated in the cozy, wood-paneled game room. With $3 Schlitz on tap and an array of tasty and surprisingly inexpensive cocktails, it’s easy to lose yourself in endless rounds of pool and foosball.

After midnight, though, it’s time for bed—but this proves to be a challenge. The crisp, masculine quarters seem to command a Scotch in memory of the patrician members who stacked Z’s after a rollicking night of fencing and poker. Never fear—you’ll sleep it off under the wonderfully light-blocking window treatments.

In the morning grab coffee and a doughnut in The Milk Room, and head out to explore Millennial Park, just steps away. Before you know it, it’s time to eat again, this time at the iconic Cherry Circle Room. Sophisticated yet utterly laid back, a formerly stuffy club dining room has been transformed into au courant restaurant. Naturally, the brunch menu is hyper-modern with a playful wink to the past.

Amy Tara Koch is on the Chicago beat for Travel + Leisure. You can follow her on Twitter at @AmyTaraKoch and Instagram at @amytarakoch.

Looking for more on hotels in Chicago? Read T+L’s Hotel Guide: Chicago.