Chicago Athletic Association

Rooms and decor

Picture a stately dark-brown Venetian Gothic building that has stood on Michigan Avenue since 1893 — the Chicago Athletic Association, once the city's elite sporting club, where the gentlemen of Chicago came to exercise, play and socialize. Today it has been carefully restored and reborn as a boutique hotel that reopened in 2015. Inside, the roughly 241 rooms and suites are styled to match the building's era — warm tones of dark wood, soft leather, classic patterned fabrics and tasteful vintage pieces that feel more like a room in an old club than a standard hotel room. Many rooms have tall windows framing Millennium Park and the Chicago skyline. Plenty of reviews agree the charm and character are what win people over, because every square inch tells the story of a historic building. From the moment you step into the high-ceilinged, dark-wood lobby, you feel this place is not like anywhere else.

Food and amenities

The most talked-about feature is the Cindy's rooftop bar, named after a former club manager, with 360-degree views down over Millennium Park, blue Lake Michigan and the city skyline. Sunset here is so good it's talked about citywide, one of the rooftop bars both tourists and Chicagoans come to check in at. But the charm isn't only on the roof — the second floor is the heart of the fun. The Game Room is a big old-club hall where guests come down to play billiards, ping-pong, shuffleboard and board games over cocktails. Next door, the Drawing Room is a grand, high-ceilinged sitting room with long windows onto Millennium Park, perfect for coffee, a book or some work. For serious cocktail fans there's the Milk Room, a tiny bar with just a few seats serving rare, exclusive cocktails, and on the food side the Cherry Circle Room serves classic American food in a vintage setting restored from the club's old dining room. There's also a 24-hour fitness center. All told, this is a hotel where you could spend the whole day and still find corners to explore.

Location and getting there

If there's an ace card, it's the near-perfect location. The Chicago Athletic Association sits on Michigan Avenue in the heart of The Loop, facing directly across to Millennium Park and the iconic The Bean (Cloud Gate). Step out the door, cross the street, and you're in the downtown park with fountains, a concert lawn and the city's favorite photo spots. Keep walking along the park another 3 minutes or so and you reach the Art Institute of Chicago, the renowned art museum with a vast collection of masterworks, and a little farther is the Lake Michigan shore and Maggie Daley Park. The State Street shopping strip and the Loop theaters are nearby too. Getting around is easy, with several CTA elevated lines nearby — Madison/Wabash station is only about a 2-minute walk and takes you across the city and onward to the airport directly. With nearly everything downtown within walking distance, couples rate the location 9.7. In short, if you want to base yourself in one spot and walk to the heart of Chicago without much driving, this location is a perfect ten.

Things to know before booking

Straight talk to help you decide — the first thing reviews flag often is that some standard rooms run fairly compact, a limit of the century-old building. Some feel the space and bathroom are smaller than the pretty photos suggest, and views vary a lot by room. If you want more space or a full Millennium Park view, upgrade to a larger room or pick one facing the park. The second is Cindy's, so popular it cuts both ways — the vibe and view are excellent, but it gets especially crowded in summer and on weekend evenings, often with a queue or a wait for a table. Even hotel guests sometimes need to allow extra time, so go before peak or ask in advance about guest access. The last point is parking: the hotel has none of its own, so you'll use valet, and downtown Chicago parking fees run fairly high for the area, so budget for it if you drive. And because it's on busy Michigan Avenue, some street-facing rooms may pick up daytime traffic noise — if you're a light sleeper, ask for a higher floor or a quieter side.

Our take

After reading through hundreds of real reviews, the Chicago Athletic Association is a boutique hotel that sells "historic-building charm, a location across from Millennium Park, and shared spaces with real character" in a way that's hard to match anywhere else. If your trip picture is waking up in a stylish old-club room, crossing the street to Millennium Park and The Bean, stopping by the Art Institute at midday, coming back to play billiards over cocktails in the Game Room in the afternoon, and closing the night with 360-degree views at Cindy's, this is a fitting and memorable choice. The only catches are the fairly compact standard rooms and the crowds at Cindy's that call for extra time. Overall we give it 8.7/10 — best for couples, solo travelers and anyone who falls for an old building with a story, who values location, atmosphere and experience over room size.