Chicago Athletic Association

The Chicago Athletic Association was built in 1893 by Henry Ives Cobb as a private men's club, in a Venetian Gothic style that has nothing to do with Chicago and looks marvellous anyway, all pointed arches and carved stone facing Michigan Avenue. The club held out until 2007. Roman and Williams converted it in 2015 and had the sense to leave most of it alone.

That restraint is the reason to stay. The public rooms are the hotel: a staircase you slow down for, a Game Room with billiard tables and a fireplace that works, a Drawing Room where the members once did whatever members did. None of it has been turned into a lobby. You can sit in these rooms all evening without buying anything and nobody comes over.

Cindy's, on the roof, is the part everyone knows. It looks straight across Millennium Park to the lake and it is properly busy, so book it. The food downstairs has turned over completely since we were there: the Cherry Circle Room closed in 2025 and is now The Ives, and the eight-seat whisky bar that was the Milk Room is now an omakase counter. Both opened after our stay.

Our room was a Classic, 23 square metres, and it was fine rather than the point. The money and the character are downstairs, which is the right way round at this price. The real caveat is the one we chose: we went in late February, which is why it cost a hundred and thirty dollars a night. Chicago in February is genuinely punishing, the rooftop is a different and much shorter proposition, and the walk to anything is a decision rather than a stroll. Go in October and you will pay more and enjoy it more.