Chicago Athletic Association Hotel

Housed in a restored Venetian Gothic building originally constructed in the 1890s, this hip hideaway is one of Chicago’s trendiest properties.

• The beautiful historic details in the hotel architecture and design
• The vibrant scene at the rooftop restaurant/terrace/lounge Cindy’s
• The cheeky in-room sports references, including pommel horses at the end of the bed and table legs encased in tennis grip wrap

Located across the street from Millennium Park, the hip Chicago Athletic Association Hotel is located in one of Chicago’s most architecturally significant buildings. Originally designed to look like a Venetian palace, the CAA was founded in 1890 as a men’s club for athletic, business and social pursuits. It closed in 2007 and reopened in 2015 with 241 restored rooms and a preserved landmark feel.

The boutique property is awash with such historical details as fencing court floorboards lining the elevator walls, ornate mosaic-tiled floors and stained-glass windows. The lobby-lounge looks a bit like a Brooklyn hipster went to town on a Harvard study, albeit in an ultra-cozy and appealing way: leather Chesterfield sofas, rich Persian carpets and carved stone fireplaces are the defining characteristics here. The rooms are a touch more subdued, with crisp white Sferra bedding, brass-accented bed frames and Carrara marble bathrooms, plus plenty of references to the building’s past life (pommel horses, shelving that was once a climbing rack, et. al). It is worth noting that the Standard rooms are, as one might expect, not as chic as the upper level rooms. They are a bit dark and have windows that open up to the backside of another building.

The hotel’s much-hyped restaurants and bars attract a cool crowd of Chicagoans. The jewel in CAA’s culinary crown is Cindy’s, the 13th-floor rooftop eatery and lounge that is a magnet for the after-5pm clique; blame it on the outside terrace with fire pits and amazing views of Millennium Park, the craft punch cocktails or the seasonal Midwest comfort food. Though windowless, Cherry Circle Room is a charmingly retro eatery with cherry paneling and cabinetry housing an impressive wine collection. The 15,000-square-foot Game Room off of the lobby acts as a playground for kids during the day and young professionals at night with entertainment such as bocce, shuffleboard, chess and more.

The CAA doesn’t want for eating and drinking establishments, and is well equipped in terms of amenities as well, including 24-hour room service and fitness facilities (fittingly enough), Heritage Bicycle rentals and complimentary WiFi.

Young couples, singles and groups of friends will dig the aggressively cool scene here. Laid-back families may enjoy the epic Game Room, though those seeking around-the-clock coddling should book elsewhere. Architecture buffs will revel in the stunningly restored building, and shouldn’t miss the guided tours of the hotel, offered through a partnership with the Art Institute of Chicago and the Chicago Architecture Foundation.