A system for facilitating freight transactions that includes a secure portal for receiving users' (carriers, forwarders, shippers, and market makers) data that includes orders and capacity postings between destinations. The system also includes a back-end modules configured for collecting capacity/shipping volume data to generate forecast data, managing derivative contracts, determining best possible routing given the orders and capacity postings, breaking the best possible routing into component segments that is then traded as derivative contracts, providing report, managing settlement and clearinghouse functions, and receiving risk assessment about the forecast data. The system further includes an interface layer for facilitating communications between the portal and the back-end modules. The system moreover includes a contract and capacity management module configured for enabling the carriers and the forwarders to strategically position their capacity. The system yet also includes a real time integration layer configured for enabling a external systems to interact with the system.