A contract pilot is an aviation professional who operates helicopters, charter planes, or another aircraft on a per-job basis. As a contract pilot, you work directly with corporate or individual clients to fly an aircraft between locations and transport passengers or cargo. Your contract may be for a single trip or multiple trips. However, you operate as an independent contractor, so you are responsible for maintaining your credentials and insurance. Working as a contract pilot provides you with greater flexibility than being a pilot for an airline or the military.