Chicago Athletic Association
12 S Michigan Ave (at E Madison St)
Chicago, IL 60603
Following a 2015 renovation, this historical building transformed into a boutique hotel with several food and drink options, including a patio-equipped Shake Shack, Drawing Room in the expansive second floor lobby, and a rooftop restaurant with views of Millennium Park. The epic game room has bocce and shuffleboard courts, a pool table, and foosball, while the restaurant, Cherry Circle Room, serves a beef-centric menu and tableside cocktails.