This beautiful gothic building dates back to the 1920s, and legend has it that Al Capone’s brother, Ralph, ran a speakeasy and casino from the penthouse during Prohibition. In 1970, Hugh Hefner and Playboy Enterprises purchased the property and it operated as Playboy Towers until 1979. The hotel revels in that history and invites guests to do so, too, during a free Friday tour at 3pm. Personally, I found the history of the hotel more interesting than its present, which feels a bit dated. Still, rooms and bathrooms are small but comfortable (upgrade to a Superior Room for more space), and the location is ideal: close to the lake, shopping, nightlife, restaurants, and more.