Provided is a flight optimization system and a method of flight optimization that includes generating flight data via an onboard aircraft system, performing a pre-flight cycle by determining an updated tail assignment plan before departure based on the flight data received in real-time from the onboard aircraft system, performing an in-flight cycle by collating and processing in-flight data and external data via an onboard network server, and transmitting the processed data to an electronic flight bag in real-time and performing flight path optimization via a path optimizer application of the electronic flight bag to be accessed by flight personnel, and performing a post-flight cycle by transmitting post-flight data to an event measurement system along with operational data to be processed and sent to a fleet support system and a maintenance system for generating updated flight plans and maintenance plans which are data-driven.