A mobile pickup unit is provided that includes storage compartments (e.g., for containing items) and is configured to travel to a user pickup area and park as close as possible to an optimal location that is determined based on the locations of users who are scheduled to utilize the mobile pickup unit. The mobile pickup unit may include or otherwise be transported by any type of mobile machine (e.g., automobile, etc.), and control of the mobile machine may be manual (e.g., a driver) or automated (e.g., directly or remotely controlled by an automated system, robotic, etc.) A parking location that is selected may be along a public street or any other available parking space, such that parking locations may be selected on a daily basis that are convenient for the users who will be utilizing the mobile pickup unit (e.g., for retrieving ordered items, dropping off returned items, etc.).