Chicago Athletic Association Hotel

The Chicago Athletic Association opened in 1893 as an elite private men’s athletic club. It operated as such until 2007, where it was abandoned for a few years before undergoing a full renovation. The designers overseeing the restoration knew not to mess with a good thing when they preserved the hotel’s Victorian Gothic features, like marble staircases, old-fashioned paneled drawing rooms, and cozy fireplaces in common areas. A traditionally masculine aesthetic is found throughout, seen in tufted leather couches, dark walls, and even pommel horses that act as bedside benches.
The property opened as a hotel in 2015, and it attracts a crowd largely of young professionals with its array of bars, beautiful aesthetic, and hip ambience. Couples, solo business travelers, and groups of friends – locals and tourists alike – can all be found hanging at rooftop bar Cindy’s, speakeasy-style Milk Room, and the Game Room bar, which has billiards, bocce bay, and shuffleboard. Other unique offerings here include Shake Shack room service and a Topgolf Swing Suite with two interactive gaming simulators for virtual golf.
There are downsides here, however, including thin walls that cause noise complaints, a daily resort fee called a “Founders Fee”, and some rooms that are quite compact.

The Chicago Athletic Association Hotel is located right on Michigan Avenue, in the heart of Chicago’s tourist and business district, making it ideal for visitors wanting a central spot to visit tourist hotspots. It’s next to Millennium Park, where famed sculpture Cloud Gate is located. The Art Institute of Chicago is on the next block, and the Willis (or Sears, if you still insist) Tower is a 15-minute walk from the hotel. Numerous restaurants, bars, and shops are within an easy walk of the hotel. Guests will have their choice of L-trains, with several stations (including those on the O’Hare and Midway routes) less than a five-minute walk from the hotel. Chicago’s O'Hare International Airport is a 30-minute drive from the property.

The hotel’s 241 guest bedrooms (including 23 suites) are handsome and contemporary, with nods to their former life as a men’s athletic club. They have dark carpeting, metal bed frames with brass accents, wood furniture, and unique leather pommel horses at the foot of the beds. Leather club chairs, wood-paneled walls, metal light fixtures, and cool artwork add attractive touches in some. However, some past guests have complained of small rooms, thin walls that cause noise issues (particularly with garbage trucks), and a lack of views and natural light.
On the plus side, rooms are well-outfitted with Sferra linens, Fairbault Woolen Mill Blankets, bedside USB charging ports, free Wi-Fi, and Bluetooth speakers in the style of old radios. Additional standard amenities consist of Sealy mattresses, minibars stocked with local labels (and crystal glasses), triple-distilled water, air-conditioning, safes, and 42-inch flat-screen TVs. Rooms don’t have coffeemakers or tea kettles, but free coffee or tea is available daily in the Cherry Circle Room downstairs. Bathrooms, done in an old-school locker-room feel, feature Carrara marble, rain showers, and C.O. Bigelow toiletries, as well as robes in the style of vintage boxing ones. The best (read: priciest) rooms overlook Millennium Park.
Suites vary in terms of layout and amenities, with some adding separate living spaces, stellar vistas, additional bedrooms, bathtubs, and/or fireplaces.

There’s more choice here than one might expect for a boutique-feeling hotel, with seven options for imbibing and dining. The flagship, 13th-floor Chicago Athletic Association Hotel rooftop restaurant is Cindy’s, which has a gorgeous indoor dining space topped by a vaulted glass ceiling, as well as an open-air terrace that overlooks Millennium Park. It’s open for lunch, dinner, and weekend brunches, serving seasonal food and tasty alcoholic punches.
The Mad Men-esque Cherry Circle Room serves elevated regional foods from breakfast until dinner. Its menu includes an array of cocktails and impressive seafood towers. There’s plenty catering to the hotel’s trend-conscious crowd, too: Game Room, a cocktail-and-beer joint features billiards, bocce, checkers, shuffleboard, and other classic games (though it sometimes closes for private events); Milk Room, an eight-seat microbar that has roots as the club’s Prohibition-era speakeasy, and a Shake Shack attached to the hotel, complete with patio. Speaking of, if you happen to spend a late night out in the Windy City, you can order Shake Shack room service (the world’s only one).
The elaborately wood-carved, cozy Drawing Room houses leather couches and three working fireplaces, and it’s a popular afternoon and evening spot. It offers pork shoulder confit and cheese and oyster plates alongside a small but effective wine list and cocktails (as well as a spirit-free drinks list targeting each of the mouth’s five taste senses). For early mornings, there’s the marble-countered Fairgrounds’ coffee on-site. Free coffee and tea are served daily at Cherry Circle Room. The daily resort fee includes discounts at Fairgrounds and Cindy’s, plus skip-the-line entry to Cindy’s Rooftop and preferred reservations in Milk Room.

Outside of restaurants and bars, there are few features at this property. The Chicago Athletic Association Hotel gym, a small 24-hour facility with retro wooden elements and art featuring a line of vintage athletes doing calisthenics, is available for guests to use. The hotel also offers discounted personal training sessions, but there’s no spa or pool available to use. The daily resort fee (called a Founder Fee here) gives guests access to the hotel’s seasonal fleet of bicycles. Guests can also sign up for one of the building’s guided architecture tours six days a week.
The hotel offers 17,000 square feet of meeting facilities on-site that are elegant and sophisticated, with polished wood-paneled walls and modern black leather armchairs. Weddings can also be arranged, with four venues available with a range of aesthetics, from a glamorous parquet-floored ballroom with crystal chandeliers to the restored old CAA basketball court (the largest, holding 500 guests), or its old indoor pool, featuring original tiled lap lanes.
Wi-Fi is free at standard speeds, though guests wishing to stream will need to upgrade for a charge to the faster internet. Self-parking is available for an expensive overnight fee, and valet parking is available up to eight hours at a time, and pets can stay free (up to two per room).