An aircraft flight risk measuring system for analyzing risks related to a flight of an aircraft. A user of the risk measuring system can be a flight dispatcher, an owner/operator, a pilot and other interested parties. The risk measuring system includes a risk management server system computer. The system computer has a two-way communication with a user computer operated by the user. An accident history database is connected to the system computer for providing accident reports related to the aircraft and other accident data. Also, a navigation database is connected to said system computer for providing airspace data, radio navigation aids, preferred routes, elevation data, geographic data and information related to a destination airport. Further, a non-static database is connected to the system computer for providing live information related to weather forecasts and data related to the aircraft's flight. As an option, a two-way communication between said system computer and an aircraft computer on board the aircraft can be included. The two-way communication used for receiving and transmitting encoded data from the aircraft when the flight is in progress.