An aircraft pairing system and method are provided to arrange for scheduling flights of two or more aircraft. The system and method allow to identify pairs of aircraft flights, wherein the aircraft can be brought together into a formation with a follower aircraft flying in the wake upwash of a leader aircraft to generate fuel savings. The system and method utilize historical flight data to generate a list of possible flight pairings and anticipated fuel savings, and live data to update the possible flight pairings and anticipated fuel savings. A display of the possible flight pairings and anticipated fuel savings is provided on a user interface. The user may accept flight pairings and extract data to modify flight plans.