Abstract: Systems and methods are provided for analyzing a cancellation policy for a trip item to determine payment parameters set for the trip item, and for each of a plurality of predetermined number of installment payments, calculating a payment period for each payment parameter set for the trip item based on a time period before payment is due to meet each payment parameter and the predetermined number of installments. The systems and methods further provide for selecting a number of predetermined installment payments of the plurality of predetermined number of installment payments that comprises an optimal payment period between a final installment payment and the start date of the trip item, generating an installment plan based on the selected number of predetermined installment payments, the installment plan comprising a date and amount for each installment payment, and causing the installment plan to be presented via the computing device.