System, apparatus and methods for automatically calculating a discount for a customer offered by a merchant through a reservation system. In one example, a reservation file is provided and contains data relating to a reservation, and transaction data relating to payment card transactions is accessed. One or more elements of the transaction data are compared against one or more elements of the reservation file to determine a match; and based on the match, the discount is electronically calculated based one or more one or more elements of the transaction data and one or more elements of the reservation file. In this way, the discount can be accurately calculated in an automatic fashion. In another embodiment, the customer may opt for a non-cash discount such as airline miles, points, or other rewards, in which case the customer may be provided with such rewards in an amount proportional to the discount.