The former is located in the Chicago Landmark Historic Michigan Boulevard District and the latter along the Magnificent Mile.

Their father John Drake (1826-1895), was also a hotelier and the business partner of Timothy Blackstone.

In 1898, Drake acquired property on the south shore of Geneva Lake, Wis., from Arthur Kaye and hired Howard Van Doren Shaw to design a summer home there for his family.

"Aloha Lodge", a Southern colonial architecture-style country estate, was completed in March 1901.

[5] He is the grandfather of the American film actress and writer Betsy Drake, who was the third wife of Hollywood actor Cary Grant,