The present disclosure involves a method that involves: receiving a request to pay a bill having a billing date; identifying a plurality of funding instruments available for paying the bill; retrieving respective billing cycles of the funding instruments; and recommending one of the funding instruments to pay the bill based on the billing date of the bill and the respective billing cycles of the funding instruments. The present disclosure also involves a system that involves: means for receiving a request to make a payment, the payment having a payment deadline; means for identifying a plurality of different funding sources; means for retrieving billing period information associated with each funding source; and means for recommending using one of the funding sources to make the payment, wherein the means for recommending includes means for comparing the payment deadline with the respective billing period information of the funding sources.