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A Pilot Instructor Jobs in Chicago, IL (NOW HIRING)

Eagle Aircraft

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Chief Flight Instructor

Chicago, IL · On-site

$83K - $104K/yr

Hold a Commercial Pilot Certificate or Airline Transport Pilot (ATP) Certificate. * Hold a current FAA Flight Instructor Certificate (CFI). * Hold the appropriate category and class ratings for the ...

Eagle Aircraft

Be Seen First

Chief Flight Instructor

Chicago, IL · On-site

$83K - $104K/yr

Hold a Commercial Pilot Certificate or Airline Transport Pilot (ATP) Certificate. * Hold a current FAA Flight Instructor Certificate (CFI). * Hold the appropriate category and class ratings for the ...

SAIC

ZAU - Remote Pilot Operator

Aurora, IL · Remote

$40K - $80K/yr

This is NOT a UAS, UAV, RPV, or DRONE pilot position. We are looking for Part-time, Remote Pilot ... Instructors) * Experience and certification in ATC Tower, TRACON or En Route simulation lab is ...

New

SAIC

ZAU - Remote Pilot Operator

Aurora, IL · Remote

$40K - $80K/yr

This is NOT a UAS, UAV, RPV, or DRONE pilot position. We are looking for a Casual, Remote Pilot ... Instructors) * Experience and certification in ATC Tower, TRACON or En Route simulation lab is ...

New

Spartan Education

FLIGHT INSTRUCTOR

West Chicago, IL · On-site

$20 - $28/hr

Flight Instructors develop pilots by emphasizing safety and risk mitigation during flight ... Maintain a consistent quality of instruction at not less than the level mandated by the school, or ...

SAIC

RTC-IL Remote Pilot Operator

Elgin, IL · On-site +1

$40K - $80K/yr

This is NOT a UAS, UAV, RPV, or DRONE pilot position. We are looking Full-time, Remote Pilot ... Instructors) * Experience and certification in ATC Tower, TRACON or En Route simulation lab is ...

SAIC

RTC-IL Remote Pilot Operator

Elgin, IL · Remote

$40K - $80K/yr

This is NOT a UAS, UAV, RPV, or DRONE pilot position. We are looking Full-time, Remote Pilot ... Instructors) * Experience and certification in ATC Tower, TRACON or En Route simulation lab is ...

SAIC

MDW Air Traffic Control Instructor

Chicago, IL

$40K - $80K/yr

This position may provide mentoring for students and Remote Pilot Operators (RPO), and may ... The CTS Instructor is a hands-on position that requires the candidate to effectively and ...

SAIC

ORD Air Traffic Control Instructor

Chicago, IL

$40K - $80K/yr

The CTS Instructor is a hands-on position that requires the candidate to effectively and ... This position will provide mentoring for students and Remote Pilot Operators (RPO) as well as ...

SAIC

ORD Air Traffic Control Instructor

Chicago, IL · On-site

$40K - $80K/yr

The CTS Instructor is a hands-on position that requires the candidate to effectively and ... This position will provide mentoring for students and Remote Pilot Operators (RPO) as well as ...

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All JobsA Pilot Instructor JobsA Pilot Instructor Jobs in Chicago, IL

A Pilot Instructor information

See Chicago, IL salary details

$40.7K

$106.1K

$176.7K

How much do a pilot instructor jobs pay per year?

As of Aug 16, 2026, the average yearly pay for a pilot instructor in Chicago, IL is $106,144.00, according to ZipRecruiter salary data. Most workers in this role earn between $86,500.00 and $130,300.00 per year, depending on experience, location, and employer.

How much do you make as a pilot instructor?

Pilot instructors typically earn between $30,000 and $70,000 annually, depending on experience, location, and the type of flight school or airline. Many instructors supplement their income with flight hours and certifications, and salaries can increase with seniority and additional qualifications.

How do you become a pilot instructor?

To become a pilot instructor, you must first obtain a commercial pilot certificate and accumulate the required flight hours. Then, you need to earn an instructor certificate by passing written and practical exams, demonstrating teaching ability and flight proficiency. Instructors often need to maintain current certifications and stay updated on regulations and safety procedures.

How long does it take to be a pilot instructor?

Becoming a pilot instructor typically requires obtaining a commercial pilot certificate, accumulating around 250 flight hours, and gaining experience as a pilot. The process usually takes several months to a year, depending on training schedules and individual progress, before qualifying to instruct other pilots.

What is the difference between A Pilot Instructor vs Flight Instructor?

AspectA Pilot InstructorFlight Instructor
CertificationsCommercial Pilot License (CPL), Certified Flight Instructor (CFI)Private Pilot License (PPL), Certified Flight Instructor (CFI)
Work EnvironmentFlight schools, airlines, corporate flight departmentsFlight schools, training academies
Employer & IndustryAviation training, airline industryFlight training, aviation education

While both roles involve flight training, a Pilot Instructor typically holds higher certifications like a Commercial Pilot License and may train pilots for airline or corporate roles. A Flight Instructor usually holds a Private Pilot License and focuses on training student pilots to obtain their initial licenses. Both roles are essential in aviation training but differ in certification levels and training scope.

What are popular job titles related to A Pilot Instructor jobs in Chicago, IL?

For A Pilot Instructor jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching A Pilot Instructor jobs in Chicago, IL look for?

The top searched job categories for A Pilot Instructor jobs in Chicago, IL are:

A Pilot Instructor jobs near you

Chief Flight Instructor

Eagle Aircraft

Chicago, IL • On-site

$83K - $104K/yr

Full-time

Medical

Posted 24 days ago

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Job description

Chief Flight Instructor: Leads the charge in ensuring our programs reflect global best practices in flight safety, compliance, and instruction. Oversees flight instruction to reinforce our reputation as a leader in aviation education.

Principal Accountabilities

  • Ensures the flight school maintains training techniques, procedures, and standards acceptable to the FAA Administrator.  Builds and maintains a culture of excellence that maintains the organization’s reputation as a top tier aviation school.
  • Conducts initial and recurring proficiency checks for all assigned flight instructors.  Ensures every student and instructor operates within established safety protocols.
  • Supervises all flight training and evaluation activities.  Coordinates instructor and student schedules to maximize educational and training outcomes.  Mentors instructors to ensure consistency, compliance and safety.
  • Serves as the primary point of contact with the local FAA Flight Standards District Office (FSDO) regarding operations, instruction, and safety matters.
  • Develops, reviews, and assists with the preparation of FAA Training Course Outlines (TCOs) and curriculum updates.  Develops and adapts training curricula to meet FAA and global standards.
  • Maintains student and instructor training records in accordance with FAA and school requirements.
  • Is available at the school or reachable by electronic means when training for an approved course is being conducted. 

Flight Time Requirements

The minimum flight experience requirements for a Chief Flight Instructor are outlined in 14 CFR § 141.35 and depend on the specific course(s) they are designated to oversee: 

Specific flight hour requirements depend on the course, such as those for recreational/private pilot certificates, instrument ratings, or other courses like commercial pilot or ATP. For detailed requirements, refer to 14 CFR 141.35 in the eCFR. Special considerations for gliders, balloons, or airships have reduced hour requirements (40%), and ground school chief instructors need one year of experience at a certificated pilot school. 

 

Qualifications

To be eligible for designation as a chief instructor for a course of training, a person must meet the requirements as outlined in § 141.35.  Here below is a brief summary.  Candidates must familiarize themselves with the FAA’s detailed requirements found at 14 CFR 141.35 in the eCFR

Minimum Chief Instructor Requirements – Instrument & Multi-Engine Training

The Chief Instructor assigned to Instrument Rating and Multi-Engine courses shall:

  • Hold a Commercial Pilot Certificate or Airline Transport Pilot (ATP) Certificate.
  • Hold a current FAA Flight Instructor Certificate (CFI).
  • Hold the appropriate category and class ratings for the aircraft used in training, including Airplane Multi-Engine Land (AMEL).
  • Hold a current Flight Instructor Instrument (CFII) certificate.
  • Meet the recent flight experience requirements of 14 CFR §61.57.
  • Successfully complete the FAA Chief Instructor knowledge and proficiency tests as required by 14 CFR Part 141.

Minimum Experience

  • At least 2,000 hours Pilot-in-Command (PIC).
  • At least 100 hours of actual or simulated instrument flight time.
  • Flight instructor experience consisting of either:
    • 3 years and 1,000 hours of flight instruction; or
    • 1,500 hours of flight instruction.
  • Instrument flight instructor experience consisting of either:
    • 2 years and 250 hours of instrument instruction; or
    • 400 hours of instrument instruction.

The Chief Instructor shall maintain all FAA certificates, ratings, qualifications, and currency necessary to conduct and supervise training in accordance with 14 CFR Parts 61, 91, and 141.

At iFly USA, we are redefining aviation education. Join us in creating the future of aviation!

Company Description

Our mission is to provide a seamless integration of safety, legality, and efficiency, bridging international aviation standards and creating unparalleled opportunities for our students.