Improving the predictability of airline schedules in the National Airspace System (NAS) has been a constant endeavor, particularly as system delays grow with ever-increasing demand. Airline schedules need to be resistant to perturbations in the system including Ground Delay Programs (GDPs) and inclement weather. The strategic search heuristic proposed in this dissertation significantly improves airline schedule reliability by assigning airport departure and arrival slots to each flight in the schedule across a network of airports. This is performed using a multi-objective optimization approach that is primarily based on historical flight and taxi times but also includes certain airline, airport, and FAA priorities. The intent of this algori...