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Weekend Flight Instructor Jobs in Portland, OR (NOW HIRING)

Requires the ability and/or willingness to work days, nights, weekends, and in remote locations on a 3-weeks on, 3-weeks off basis * 401k with up to 4.5% company matching * Medical insurance package ...

Requires the ability and/or willingness to work days, nights, weekends, and in remote locations on a 3-weeks on, 3-weeks off basis What You'll Get * 401k with up to 4.5% company matching * Medical ...

Requires the ability and/or willingness to work days, nights, weekends, and in remote locations on a 3-weeks on, 3-weeks off basis What You'll Get * 401k with up to 4.5% company matching * Medical ...

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Showing results 1-20

Weekend Flight Instructor information

See Portland, OR salary details

$25.5K

$96.7K

$148.7K

How much do weekend flight instructor jobs pay per year?

As of Jun 10, 2026, the average yearly pay for weekend flight instructor in Portland, OR is $96,690.00, according to ZipRecruiter salary data. Most workers in this role earn between $70,500.00 and $114,400.00 per year, depending on experience, location, and employer.

What is a Weekend Flight Instructor job?

A Weekend Flight Instructor is a certified flight instructor (CFI) who provides flying lessons primarily on weekends. This role is ideal for instructors who have a full-time job elsewhere or prefer a flexible schedule. Responsibilities include teaching flight maneuvers, conducting ground instruction, and ensuring student pilots meet safety and regulatory standards. Weekend Flight Instructors typically work with student pilots pursuing private, commercial, or other pilot certifications.

What does a typical weekend schedule look like for a Weekend Flight Instructor, and how are student lessons structured?

As a Weekend Flight Instructor, your schedule is typically concentrated on Saturdays and Sundays, with lessons planned throughout the day to accommodate students who are balancing flight training with weekday commitments. Most instructors manage multiple students, dividing time between pre-flight briefings, in-flight instruction, and post-flight debriefs. Lessons are usually tailored to each student's progress and may include ground school segments, simulator sessions, and real-world flight time. You will often collaborate with other instructors and administrative staff to coordinate aircraft availability and manage training documentation. This structure allows you to maximize instructional time and provide focused, individualized training within the constraints of a weekend-only role.

What are the key skills and qualifications needed to thrive in the Weekend Flight Instructor position, and why are they important?

To thrive as a Weekend Flight Instructor, you need a certified pilot’s license with instructor credentials, strong aviation knowledge, and a solid record of safe flying. Familiarity with aircraft systems, flight simulators, and digital aviation logbooks or scheduling tools is essential. Excellent communication, patience, and motivational skills help create a positive learning environment for student pilots. These qualifications are crucial for ensuring safety, effective training, and fostering student success during condensed weekend instruction sessions.

What are the most commonly searched types of Flight Instructor jobs in Portland, OR? The most popular types of Flight Instructor jobs in Portland, OR are:
Line Pilot

Full-time

Medical, Dental, Vision, Life, Retirement

Posted 6 days ago


Quanta Services rating

7.2

Company rating: 7.2 out of 10

Based on 51 frontline employees who took The Breakroom Quiz

44th of 78 rated construction


Job description

Winco is an agile aviation business with decades of proven innovation and service to the powerline construction and maintenance industry. We provide best-in-breed utility helicopters and crews to support projects of all complexities and sizes throughout the United States. We are a team of quiet professionals who get the job done safely and to the specification and satisfaction of our customers. Our approach centers around providing the best maintained aircraft, the best trained aviation teams (Pilots, Mechanics, Linemen & Groundmen), and the best results in terms of safe and efficient production for our customers.


Winco Powerline Services is seeking experienced candidates for Utility/Powerline Pilot. Will be flying in the wire environment in support of powerline construction with human external loads, non-human loads, class A loads (skid work), and class C loads (wire pull). This position requires pilots who are willing to clean aircraft and other miscellaneous non-pilot duties. We are looking for someone who is self-motivated and will represent Winco in a professional manner.


  • Work a rotational schedule of three (3) weeks on and three (3) weeks off.
  • Fly in the wire environment in support of powerline construction.
  • Carry human external loads, non-human loads, class A loads (skid work), and class C loads (wire pull).
  • Clean aircraft and perform other miscellaneous non-pilot duties.
  • Adhere to all Company Safety and Health Policies while in the course of conducting Company business.

  • FAA Commercial or ATP Helicopter
  • Current 2nd Class medical certificate
  • 200 Longline / Vertical Reference hours
  • 50 hours make and model (MD 500 series)
  • Pass FAA/DOT drug test (pre-hire and randoms)
  • Legal US work status
  • Requires the ability and/or willingness to work days, nights, weekends, and in remote locations on a 3-weeks on, 3-weeks off basis

  • 401k with up to 4.5% company matching
  • Medical insurance package with PPO and HSA options
  • Dental, vision, and life insurance

All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of race, color, religion, national origin or ancestry, sex (including gender, pregnancy, sexual orientation, and/or gender identity), age, disability, genetic information, veteran status, and/or any other basis protected by applicable federal, state or local law.
We are an Equal Opportunity Employer, including disability and protected veteran status.
We prohibit all types of discrimination and are committed to providing access and equal opportunity for individuals with disabilities. For additional information or if reasonable accommodation is needed to participate in the job application, interview, or hiring processes or to perform the essential functions of a position, please contact us the Company’s Human Resources department.


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