Chertkov was born in 1854 in St. Petersburg, Russia into a wealthy and aristocratic family. His mother (to whom he felt especially close), Elizaveta Ivanovna, born Countess Chernysheva-Kruglikova, was known among her circle in St. Petersburg society for her beauty, intellect, authoritativeness and tact. His father, Grigorii Ivanovich, was aide-de-camp under Nikolai I, Adjutant-General under Alexander II and Alexander III, known in military circles for his front-line service and military bearing. The couple enjoyed imperial favour so much that Alexander II and Alexander III visited their home.