In this paper, we jointly integrate route-reservations with a pricing mechanism to evaluate the effect of congestion pricing on the driver departure time choices. Route-reservations have shown to be a durable congestion mitigation mechanism that can achieve up to 70% reduction in travel times. Unfortunately, this improvement is achieved only when the majority of the drivers comply with the suggested routes and departure times. Therefore, a pricing mechanism is proposed that allows drivers to deviate from the suggested departure times. To identify the departure time choices of drivers we explicitly take into account their desired departure time from their origin and also the start time of the activity they are planning to perform. The proposed flexible route-reservation framework is evaluated in a microscopic simulation with results demonstrating how the introduced pricing mechanism can eliminate congestion while allowing flexibility to drivers to deviated from the suggested departure time.