Author: Dominic Bonvissuto
I played a fun game the other day. I typed “Chicago” into the destination field on Hotels.com, entered in a late January weekend into the check-in/check-out slot, checked the 4-star and 5-star boxes and clicked “search.” The results came back featuring dozens of luxury options in prime Chicago areas with nightly rates well under $200. I was perplexed.
Then I checked Weather.com, saw all the wind and snow emojis and numbers like “17°” and was like, Oooooh, riiiiiight.
The winter clearly is the best time to visit the Windy City if you like saving money on hotels, but not if you like feeling your face when you walk outside.
The winter clearly is the best time to visit the Windy City if you like saving money on hotels, but not if you like feeling your face when you walk outside. Regardless of when you go, however, I’ve got a recommendation for where you should stay.
A colleague of my wife’s is a magazine editor in Chicago and when I asked her what I should do on a free night in the city, she mentioned having drinks at one of the bars in the Chicago Athletic Association hotel. Intrigued by the name—I was in the city for reasons related to my day job in sports—I did some looking around. Fifteen minutes later, I was booking a room and texting Chicago friends to meet me there for drinks.
What a concept. Chicago Athletic was a men’s social club established in the 1890s and existed as a private, members-only space for the city’s elite to gather until 2007, when it shuttered. The historic Michigan Avenue property bounced around development groups during the recession before it landed in the hands of an investment firm run by the son of a hotel magnate. It re-opened as a hotel in May 2015.
If you like history or sports or both, Chicago Athletic is a must-visit: the place exudes both at every turn. Start with the guest rooms. There, you’ll find unique details that give a wink and nod to the building’s past. Things like boxing corner stools in the bathroom, pommel horses repurposed as bed benches and desks anchored to vintage stretching boards. Wait, is that an old gymnasium light hung from the ceiling? Yes it is.
Other spaces in the hotel proudly display the history, too. There’s the century-old gymnasium on the fourth floor where guests can shoot hoops when it’s not rented out for private parties. A wood carving honoring the origins of football sits above a fireplace in the lobby, where anyone can come and take advantage of the free WiFi and communal tables. And the Shake Shack on the ground floor is where the Turkish bath used to be and is adjacent to a drained swimming pool, featuring the club’s familiar logo.
The real stars of the hotel are its restaurants and bars. My friends and I enjoyed steak tartare, mussels and too many glasses of wine at the Cherry Circle Room, a dark, window-less space tucked away on the second floor where Chicago Athletic members used to go when they didn’t want to be seen. It’s right next to the Game Room, the former billiards room of the social club that has been transformed into a bar-game wonderland featuring foosball, shuffleboard and a full-size bocce court.The crown jewel of Chicago Athletic is Cindy’s, a rooftop restaurant with sweeping views of Millennium Park and a large open-air terrace that I can confirm is fun for exactly 15 seconds in January. There’s also Milk Room, a coffee spot during the day and a new-school speakeasy at night, plus the Shake Shack on the ground floor. And in news that I can’t believe didn’t make front page of the Tribune, Chicago Athletic GM Patrick Hatton told me they’re finalizing details to incorporate Shake Shack into room service menus, which is both brilliant and dangerous.
Perhaps the best vote of confidence given to Chicago Athletic came from my 22-year-old, fresh-out-of-Northwestern coworker. Told about all the bars, the Game Room and the historic sports vibe that permeates the place, this former cheerleader announced in all her millennial jubilance: “I want to have my Michael Jordan birthday there! You know, 23!” Hey, just do it.
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