Chicago Athletic Association Gift Shop

The 18 Best Luxury and Boutique Hotels in Chicago to Book - AFAR

"Set directly across from the Art Institute, this former members-only men’s gymnasium retains a retro, clubby vibe with a fireplace-lit lobby, an old swimming pool repurposed as an events space, and a rooftop restaurant with terrace views over Millennium Park, Frank Gehry’s bandshell, and Anish Kapoor’s Cloud Gate. The Roman & Williams–designed second-floor room opens onto a lively games area with table games and darts; tucked-away features include a Prohibition-era six-seat bar and the James Beard Award–winning Cherry Circle Room, a dark, meat-forward restaurant with a circulating martini cart. Guest rooms in the 1893 landmark reference the building’s athletic past—gym-horse foot beds, working fireplaces, plasterwork ceilings, and carved wood wainscoting—creating a cozy, wintry ambience that makes it a popular weekend choice; the property also emphasizes water conservation, local sourcing, and strict recycling for eco-conscious travelers." - Heidi Mitchell