Chicago Athletic Association
Our favorite design company, Roman & Williams, meticulously restored this Michigan Avenue behemoth to be a cross between a Gothic cathedral, Beaux Arts athletic club, and a man cave. In homage to its history (take a guess based on the name), the rooms are equipped with pommel-horse benches, boxing-style robes, and the like. Between the Shake Shack on the ground floor, the Cherry Circle Room (the restaurant from the Longman & Eagle crew) off the lobby, the game room (billiards, bocce, foosball, and shuffleboard), the reservation-only eight-seat cocktail bar, and the raucous rooftop lounge with sweeping views of Millennium Park, there’s no real reason to leave the premises. Funny, since it couldn’t be in a better location.
PRO TIP: Rooms on a higher floor, overlooking the park, are worth the splurge.
THE DETAILS: Rooms from $249.
