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Weekend Chief Flight Instructor Jobs in Chicago, IL

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Chief Flight Instructor

Chicago, IL · On-site

$83K - $104K/yr

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 ...

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Chief Flight Instructor

Chicago, IL · On-site

$83K - $104K/yr

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 ...

Manage duty, flight, and rest times to requirements of both the company and CFRs * Maintain ... System Chief Pilot * Ability to work nights, weekends, and holidays * Bachelor's degree or ...

SIC- Gulfstream G200

Wheeling, IL · On-site

$124K - $160K/yr

Manage duty, flight, and rest times to requirements of both the company and CFRs * Maintain ... System Chief Pilot * Ability to work nights, weekends, and holidays * Bachelor's degree or ...

Manage duty, flight, and rest times to requirements of both the company and CFRs * Maintain ... System Chief Pilot * Ability to work nights, weekends, and holidays * Bachelor's degree or ...

Lead Math Instructor

Wood Dale, IL · On-site

$20 - $22/hr

Consistent, part-time hours after school and on weekends * A fun, supportive, and encouraging work ... Mathnasium's Chief Instructional Officer and a teacher and math teaching consultant in the Los ...

Lead Math Instructor

Wood Dale, IL · On-site

$20 - $22/hr

Consistent, part-time hours after school and on weekends * A fun, supportive, and encouraging work ... Mathnasium's Chief Instructional Officer and a teacher and math teaching consultant in the Los ...

Aircraft Mechanic

Chicago, IL

$29.50 - $39/hr

Amazing employee flight privileges within the American Airlines global network * Training and ... Willing and able to work rotating shifts including, nights, holidays, weekends and days off

Military Security Officer

Palatine, IL

$17.50 - $22.25/hr

... weekends, and holidays, to provide 24/7 security and law enforcement coverage; exposure to ... flight lines, harbor security boats, and in patrol vehicles, kennels, armories, and security ...

Military Security Officer

Harvey, IL

$16.50 - $21/hr

... weekends, and holidays, to provide 24/7 security and law enforcement coverage; exposure to ... flight lines, harbor security boats, and in patrol vehicles, kennels, armories, and security ...

Military Security Officer

Bannockburn, IL

$17.75 - $22.75/hr

... weekends, and holidays, to provide 24/7 security and law enforcement coverage; exposure to ... flight lines, harbor security boats, and in patrol vehicles, kennels, armories, and security ...

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Weekend Chief Flight Instructor information

See Chicago, IL salary details

$25.8K

$97.5K

$149.9K

How much do weekend chief flight instructor jobs pay per year?

As of Aug 21, 2026, the average yearly pay for weekend chief flight instructor in Chicago, IL is $97,472.00, according to ZipRecruiter salary data. Most workers in this role earn between $71,100.00 and $115,400.00 per year, depending on experience, location, and employer.

What is the difference between Weekend Chief Flight Instructor vs Flight Instructor?

AspectWeekend Chief Flight InstructorFlight Instructor
CertificationsCommercial Pilot Certificate, Certified Flight Instructor (CFI), and often a Certified Flight Instructor-Instrument (CFII)Private Pilot Certificate, Certified Flight Instructor (CFI)
Work EnvironmentPrimarily weekends, overseeing flight training operations, managing other instructorsDaily flight training, instructing students, conducting solo flights
Employer & Industry UsageFlight schools, flight academies, primarily weekend operationsFlight schools, flying clubs, individual instructors

The Weekend Chief Flight Instructor typically holds advanced certifications and manages flight training during weekends, often overseeing other instructors. In contrast, a Flight Instructor primarily conducts flight lessons and solo training sessions. The roles differ mainly in scope and responsibilities, with the Weekend Chief focusing on administrative oversight during weekends, while the Flight Instructor focuses on direct instruction.

How much do Weekend Chief Flight Instructors make?

Weekend Chief Flight Instructors typically earn between $20 and $50 per hour, depending on experience, location, and the flight school. Their compensation may include hourly rates, bonuses, or stipends, and they often hold certifications such as Certified Flight Instructor (CFI).

What are the most commonly searched types of Chief Flight Instructor jobs in Chicago, IL?

The most popular types of Chief Flight Instructor jobs in Chicago, IL are:

Chief Flight Instructor

Eagle Aircraft

Chicago, IL • On-site

$83K - $104K/yr

Full-time

Medical

Posted 28 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.