Update: I stayed at the CAA again more recently and am happy to say that they have brightened up the rooms.
Chicago’s newest hotel, which takes its name from the refurbished historical Chicago Athletic Association building where it is housed, has great bars and eateries but somewhat disappointing rooms. I chose this one-month old hotel as it’s well located across the road from the Millennial Park. After noting that it has been featured in the latest issue of Vanity Fair, and houses one of the hot new restaurants (according to Zagat) in addition to Shake Shack, I was excited to check this place out.

According to my cab driver, I was the first person he’s dropped off at this one-month old boutique hotel, the result of an extensive renovation of the 122 year-old Venetian Gothic styled Chicago Athletic Association building. Besides the location, the lobby, eateries and the roof top bar are big pluses to this hotel.
The positives – an inviting lobby and good food. After a 26 hour flight from Singapore, the first thing I wanted besides a shower was a Shake Shack burger. So I hopped down to the ground floor for my Shack burger with cheese. Not many hotels can boast about having Shake Shack among its eateries.


The lobby, on the second floor, is impressive – large with high ceilings and a turn of the century feel in the extensive woodwork. It’s a very comfortable lobby with a number of sofas, chairs (including rocking chairs) and a couple of fireplaces. The latter is likely to be very welcome in a cold Chicago winter.




Behind the lobby on the second floor is the Milk Room, an alcove serving coffee and pastries, which is probably handy for those looking for a quick breakfast or pick up. Further in is the Game Room – so called for the pool tables, and a full length boules pitch. There’s a bar here so you can have a good drink too.

Further in through the Game Room is the Cherry Circle. This is, according to Zagat, a popular new restaurant. The food is really good here and while it wasn’t packed at 7am on a weekday, I’m sure it’s packed on weekends. The bar is well stocked – I saw the Yamazaki 18 year-old whiskey on the shelf. I liked the staff here as well – friendly but not in the exaggerated superficial manner you get sometimes.

My breakfast of two eggs, bacon, hash browns and toast was USD10. The hash browns (the crispy kind) included scallions in them. The toast was grilled. Excellent! I also had a late dinner of beet salad and goat cheese except that the goat cheese was terrine like after being partly seeped in beet juice and a gelatin. Outstanding! Alas, no good pictures (didn’t have my DSLR with me) and the room was too dim for my iPhone as I don’t use a flash.

The rooftop bar, Cindy’s, is really popular with visitors and locals. I noticed a line every night to get into Cindy’s and I think it’s because there aren’t too many places where you can grab a cocktail and some decent food and relax with a nice view of the park.


The Negatives – Dim Rooms, Weak Wifi. The rooms, unfortunately fall somewhat short unless you like living in darkness and the hotel wifi, while free, is patchy. The TripAdvisor comments were certainly on point about the dim rooms. Not a big issue if you read from devices like the iPad but certainly annoying if you still use books. So this makes this hotel difficult if you’re staying for business and need to do work in the room. On the plus side, the rooms are spacious – more than enough to open up large suitcases. I stayed in a corner king room but
Overall, a Decent Place to Stay for a Holiday. In terms of the comfort level of the rooms, it is by far not as good as The Langham (but whose room rates are also twice that of the Chicago Athletic Association) but I don’t think it’s reaching for that same luxury status anyway. But I do think the food options are better at the Chicago Athletic Association hotel.
If I’m on holiday, I think I would stay here again because I think the food is great and convenient and service is warm and friendly. But for those sensitive to room comfort or who need to work in the hotel, there are probably better options (at least until they fix the two issues).
Chicago Athletic Association website: http://chicagoathletichotel.com