To say the Chicago Athletic Association is beautiful is to put it mildly. Stay in one of the 241 luxury boutique rooms—throwbacks to the club rooms of athletic associations long gone. Look out at Lake Michigan from Cindy’s rooftop restaurant to more great food and drink at Cherry Circle Room. You’ll also love the Game Room, with its private alley entrance and bocce, shuffleboard and billiards. Find access to everything you need and more in this wonderfully restored 1890s building.
Where is it? South Michigan Ave, with an unparalleled view of Millennium Park.
Which room? Holy Cow Suite. These aptly named accommodations are large, luxurious and likely to leave you speechless (apart from a holy cow utterance, naturally).
Time Out tip: Believe it or not, there's an onsite Shake Shack. It'd be rude not to grab a burger and shake… Absolutely irresistible.