Chesapeake Sport Pilot is actively seeking additional part-time flight instructors to join its staff.

Do you have a passion for flying and a love of sharing that passion for flight with others? If so, Chesapeake Sport Pilot would love to hear from you! We are currently hiring CFIs to teach the next generation of aviators the art of aviation.

Chesapeake Sport Pilot is the nation’s largest sport pilot flight school, having flown more than 20,000 hours on light sport aircraft. We are located at the beautiful Bay Bridge Airport on Kent Island where we maintain a fleet of Van’s RV-12 aircraft as well as Sky Arrows, Tecnam Eaglets, and a Searey. Our staff is composed of highly experienced, part-time flight instructors who train primary students towards sport, recreational, and private pilot certificates, give flight reviews, perform aircraft checkouts for renters, and do seaplane ratings. Our primary focus is light sport flight instruction which is performed entirely in day VFR conditions. Sport pilot rules do not require a medical for the student or instructor!

Light sport instruction is similar to private instruction with a greater focus on basic skills such as attitude flying, grass field operations, pilotage, and dead reckoning. There is no distance limitation for light sport pilots or aircraft. Light sport primary students typically fly about twice a week and complete their course in less than a year, eliminating the lengthy time commitment often required of instructors training private pilot students. Instructors use the company syllabus and are covered by company insurance while maintaining an independent status allowing complete flexibility of scheduling. We offer generous commissions with no minimum time commitment.

If you think you might be interested in joining our team of great instructors please give us a call at 410-604-1717 to set up a meeting and learn about our school. We look forward to hearing from you.


Chesapeake Sport Pilot is actively seeking a part or full-time A&P or LSRM.

Chesapeake Sport Pilot is currently seeking a part or full time A&P or LSRM to maintain our growing fleet of light sport aircraft.  This is not just a chance to turn a wrench to make a buck, but an opportunity to join a unique community of students, instructors, pilots, and leaseback owners. The ideal candidate will be able and willing to work a flexible schedule including evenings and weekends during the busy season and will have excellent interpersonal skills with which to communicate to customers, leaseback owners and staff. Rotax certification and a private pilot certificate (or higher) is a big plus. High standards of care and service are a must. Position includes opportunity to work on and fly really cool planes.

Please give us a call at 410-604-1717 if you are interested.