A vehicle charging system includes a vehicle propelled by an electric machine powered by a chargeable energy storage system. The charging system also includes a controller programmed to predict at least one upcoming plug-in event based on historical charging data, and define a plug-in routine based on a plurality of upcoming plug-in events. The controller is also programmed to set a charging schedule to coincide with the plug-in routine such that a target state of charge (SOC) is achieved at a conclusion of each of the plurality of upcoming plug-in events. Each target SOC corresponding to a plug-in event is based on minimizing a charging energy cost of the plug-in routine and an expected energy depletion ahead of a next subsequent plug-in event.