I stayed at a Chicago hotel that was once a Gilded Age men’s club. The history drew me in, but playful details won me over.

I stayed at a Chicago hotel that was once a Gilded Age men's club. The history drew me in, but playful details won me over. By ...

September 20, 2026

I stayed at a Chicago hotel that was once a Gilded Age men's club. The history drew me in, but playful details won me over.

Joey Hadden

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Ornate lobby with gold coffered ceiling, marble columns, chandeliers, staircases, and black-and-white checkered floor. — The Chicago Athletic Association is a hotel that was once an ultra-exclusive gentlemen's club. Business Insider's reporter booked a stay.
Joey Hadden/Business Insider

I've never been good at sports, and I've never been fond of exercise, so you might be wondering why I chose the Chicago Athletic Association when booking hotels for my first-ever trip to the city.

I wanted to step back in time. The Gilded Age hotel was a private club where professional athletes and high-profile individuals trained and socialized from 1893 to 2007.

Following its closure and a lengthy transformation project, the Chicago Athletic Association reopened as a hotel in 2015. I spent one night there in February for $250. It felt extremely luxurious for the price point, and some surprising details made me certain I'd book it again.

Parts of my stay felt like a time warp, but the hotel's history also came out in ways I didn't see coming.

Welcome to the Chicago Athletic Association, the 19th-century private club that's now a hotel.

The exterior of the Chicago Athletic Association — The Chicago Athletic Association is in Downtown Chicago.
Joey Hadden/Business Insider

The Venetian-Gothic-style building was designed by architect and club member Henry Ives Cobb, who took inspiration from the Doge's Palace in Venice, according to the hotel's website.

The hotel stood out to me among modern buildings on Michigan Avenue in Downtown Chicago. It's just across from Millennium Park and the Bean (formally known as Cloud Gate) and within walking distance of many tourist hot spots like the Art Institute of Chicago, the Chicago Theater, and the Chicago Riverwalk.

Inside, the past lives on.

A wooden glass case displays historical facts and relics from the Chicago Athletic Association — Historic literature is displayed in the hotel's display cases.
Joey Hadden/Business Insider

The Chicago Athletic Association began as a Gilded Age gentlemen's club joined by influential sports icons. Membership opened to women in 1972.

It was a stomping ground for industry moguls like William Wrigley and Marshall Field. It was a training base for five-time Olympic gold-medal swimmer Johnny Weissmuller and the first professional football player, William "Pudge" Heffelfinger.

The building's history is celebrated inside the hotel, with 19th-century relics and refurbished materials, from wood paneling to marble flooring, Elizabeth Story, the hotel's sales and marketing director, told Business Insider.

As I stepped into the lobby, I felt like I'd traveled back in time.

Inside the dimly lit hotel lobby with dark, wooden detailing — A peek inside the lobby.
Joey Hadden/Business Insider

The lobby, also known as the drawing room, looked as if it had been designed 100 years ago, with restored 19th-century trim, moldings, and replicated historic details.

"Teams of craftsmen restored the 1893 grandeur of the Lobby Lounge by removing, refinishing, and reinstalling every piece of millwork, and recreating original light fixtures from old photographs," Story said.

I noticed other contemporary details that pay tribute to the city and club's history. The check-in desk, designed with long strips of wood in different colors, was inspired by vintage athletic equipment.

"A mural above the desk depicts the elevated train tracks that encircle Chicago's Loop," Story added.

Restored Gilded Age interiors made communal spaces look as lavish as they were historic.

Inside the hotel, a grand marble staircase at the back of a bright, empty hall with gold moldings on the ceilings — A common area in the hotel.
Joey Hadden/Business Insider

I was mesmerized by the preserved luxury finishings as I walked through the hotel. Restored Italian columns, stained-glass windows, and golden doors made me feel as if I were inside a palace.

The ballrooms had an old-world, luxury feel.

Ornate historic interior with stained-glass windows, carved wood paneling, marble floor, decorative ceiling, and lit fireplace. — Inside the White City Ballroom.
Chicago Athletic Association

The hotel had many event spaces, including the White City Ballroom. During the restoration process, Story said that the Italian Carrara marble floor was buried under an inch and a half of carpet, glue, and concrete.

I was surprised by another event space that used to be a swimming pool.

Empty grand interior hall with marble columns, ornate ceiling lighting, and a large roundel design on the floor. — What was once a swimming pool is now an event space.
Chicago Athletic Association

Known as "The Tank," this space still has the swimming lane flooring tiles from its pool days.

"Artists hand-made 167 individual stalactites as part of the atmospheric design," Story said.

Although the highlight of this room is the historic pool tiles, I thought repurposing the space for events was surprising and innovative.

The game room had a mix of historic and fresh details.

Inside an empty game room with a foosball table in the foreground — A peek inside the game room.
Joey Hadden/Business Insider

The game room was the billiards room back in the club days, Story said.

It didn't feel frozen in time like some of the other spaces. The walls blended antique woodwork with whimsical murals, such as chalkboard sketches of athletes and an aerial view of a basketball court. I thought it was a playful, creative way to showcase the building's history.

Some aspects of the hotel were completely new, like the rooftop bar and restaurant.

Inside an empty restaurant dining room with windowed ceilings — Inside Cindy's Rooftop.
Joey Hadden/Business Insider

"The past was honored at every turn, but the transformation also called for thoughtful new additions," Story explained.

For example, Cindy's, the rooftop restaurant and bar, was built ahead of the hotel's 2015 opening.

I thought the space had a midcentury modern vibe with vintage influence. Cindy's brought the outdoors in with a steel-framed, windowed pavilion inspired by 19th-century train sheds.

The fitness center was sleek and modern.

Cardio machines in the gym at the Chicago Athletic Association — Inside the fitness center.
Joey Hadden/Business Insider

Here, I found cardio machines with tablet attachments and fun cartoons of men stretching on the walls. The fitness center is open 24 hours a day.

My room had a vintage aesthetic without feeling dated.

Inside a room at the Chicago Athletic Association, there's a bed in between two nightstands and two windows on the left wall — Inside the author's room.
Joey Hadden/Business Insider

I booked a standard room with a comfy king-sized bed and a downtown view for about $250 a night. I immediately noticed the custom metal bedframe with brass accents — a vintage design inspired by the 19th-century club.

The furniture creatively combined elements of old-fashioned gym equipment in a functional way.

A desk, TV, and bar in front of the bed in the hotel room — Another view of the room.
Joey Hadden/Business Insider

The desk was unlike any I'd seen before. Wooden bars, inspired by stretching racks, climbed the wall to a netted shelf that appeared large enough to hold a typical checked suitcase.

The bars were cleverly used as vertical storage, with leather pouches of varying sizes hanging from them. I used these pockets to store my wallet, keys, and chargers during my stay.

The bathroom blended old-school locker room vibes with opulence.

A composite image of the hotel bathroom seen from two angles — Inside the author's bathroom.
Joey Hadden/Business Insider

"The bathrooms were conceived as a quiet luxury counterpoint," Story said. A black-and-white palette and a simple striped backsplash were paired with a Carrara marble vanity and a rainfall shower.

There was also a boxing-style robe in the bathroom, which almost made me feel like an athlete myself.

At the Chicago Athletic Association, I got my trip back in time, with some surprises.

Inside the hotel, there are intricate moldings on the walls and elevators on the right — A common space in the hotel.
Joey Hadden/Business Insider

While parts of the hotel felt 100 years old, fresh designs inspired by its private-club past gave other spaces a modern twist.

"The goal was never a museum-quality freeze in time, but something more alive," Story said. "A touch of disorder in the new space was introduced to draw in a younger generation, balanced bravely with references to the building's past."

From the palace-like common spaces to the creative nods to the past, the Chicago Athletic Association was more luxurious and distinctive than I expected for $250 a night. I would definitely stay there again, and maybe next time, I'll bring a jock with me.

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I stayed at a Chicago hotel that was once a Gilded Age men’s club. The history drew me in, but playful details won me over.

I stayed at a Chicago hotel that was once a Gilded Age men's club. The history drew me in, but playful details won me over. By ...