The Chicago Athletic Association occupies a landmark 1890s Venetian Gothic building on Michigan Avenue, directly across from Millennium Park in the Loop. Once an exclusive athletic club, it was restored into one of the city's most characterful boutique hotels, with richly detailed historic interiors, the popular Game Room (a bar with billiards and bocce), the Cherry Circle Room restaurant, and Cindy's, a rooftop bar with one of the best views over Millennium Park and the lake.
The Chicago Athletic Association Hotel is set in a Venetian Gothic landmark from the 1890s on Michigan Avenue, facing Millennium Park across the street in the heart of the Loop. Originally an elite private athletic club, the building was painstakingly restored and reopened as a boutique hotel that leans fully into its history — carved woodwork, original detailing, vintage-inspired rooms, and grand public spaces.
Its social spaces are destinations in their own right, drawing locals as much as guests. The Game Room is a lively second-floor bar with billiards, board games, and bocce; the Cherry Circle Room is a well-regarded restaurant and cocktail bar; and Cindy's, the rooftop bar, has one of the best vantage points in the city, looking directly across Millennium Park to Lake Michigan. Rooms range from compact to spacious, all in a polished historic style.
The location is hard to beat for sightseeing: Millennium Park and the Art Institute are across the street, the river and Riverwalk are a short walk north, and the Loop's theaters and architecture surround it. For travelers who want character, atmosphere, and a central Loop base over resort-style amenities, it's a top pick.
Why stay here
- ✓Cindy’s rooftop bar
- ✓Game Room bar (billiards, bocce)
- ✓Cherry Circle Room restaurant
- ✓Historic restored interiors
- ✓Fitness center
- ✓Free WiFi
- ✓Across from Millennium Park
Good questions
What was the building originally?+
An exclusive private athletic club, built in the 1890s in Venetian Gothic style on Michigan Avenue. It was restored and reopened as a boutique hotel, preserving its historic interiors.
What's the rooftop bar?+
Cindy's, with one of the best views in the city — directly across Millennium Park toward Lake Michigan. It's popular with locals and visitors alike, so expect crowds at peak times.
How's the location for sightseeing?+
Excellent — directly across from Millennium Park and the Art Institute, a short walk to the river and Riverwalk, and surrounded by the Loop's theaters and architecture.
