Abstract: A flight itinerary alerting system for monitoring a flight itinerary includes a monitoring system storing flight itinerary data like pilot contact data, first tier contact data, and second tier contact data. An alert routine executable on the monitoring system i) determines first or second tier alert conditions if no deactivation message is received upon expiry of a respective first or second duration following the expected arrival time, and ii) send an alert message through a communication network to a computer device of a corresponding first or second tier contact person upon determination of the respective alert condition. The multiple tiers of contact data with respective alerting criteria allows quick determination if search and rescue should be contacted with inherent redundancy, thus preventing overdue aircraft from being overlooked, while also minimizing false alarms in reporting overdue aircraft to search and rescue which might reasonably be accounted for by responsible persons.