A user places an order on a merchant website associated with a merchant system via a user computing device. The user selects an option for delivery to the user computing device location within a delivery area during a delivery time window and authorizes a delivery system to log the location of the user computing device during and/or a period of time before the delivery time window. When the delivery time window arrives, the delivery system provides a delivery route to a delivery agent computing device. When the delivery agent arrives at the user computing device's location, the user receives an alert that the delivery agent has arrived and receives a package from the delivery agent. If the user does not remain within the delivery area, the user may cancel the order and the delivery, may reschedule the delivery, and/or may accept delivery of the order to a fixed shipping address.