The Drake Oak Brook, Autograph Collection

"Built in 1962 as an outpost of the celebrated Drake Hotel on Chicago’s Michigan Avenue, the Drake Oak Brook has always been such a trendsetter that it has attracted the likes of Frank Sinatra, Prince Charles, and Arnold Palmer deep into the Chicagoland ‘burbs over its six decades. There’s a masculine, mid-century edge to the newly renovated guest rooms, many of which feature herringbone oak-wood floors and well-stocked bar carts. The Colonial Room restaurant offers high tea in the afternoons and a menu of unmistakably retro dishes come dinnertime, from wedge salads to shrimp cocktail. And you could almost imagine Ol’ Blue Eyes himself slumping into one of the fireside leather chairs at the Polo Lounge and ordering a signature Drake Manhattan."