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Overnight Chief Flight Instructor Jobs in Chicago, IL

Eagle Aircraft

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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 ...

Eagle Aircraft

Be Seen First

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 ...

Spartan Education

FLIGHT INSTRUCTOR

West Chicago, IL

$20 - $28/hr

Flight Instructors develop pilots by emphasizing safety and risk mitigation during flight ... FAA Class III Medical required Travel Overnight flight or night flights may be required. Physical ...

All JobsChief Flight Instructor JobsOvernight Chief Flight Instructor JobsOvernight Chief Flight Instructor Jobs in Chicago, IL

Overnight Chief Flight Instructor information

See Chicago, IL salary details

$15

$33

$59

How much do overnight chief flight instructor jobs pay per hour?

As of Aug 21, 2026, the average hourly pay for overnight chief flight instructor in Chicago, IL is $33.52, according to ZipRecruiter salary data. Most workers in this role earn between $26.25 and $35.67 per hour, depending on experience, location, and employer.

What is an overnight chief flight instructor?

Overnight Chief Flight Instructors are aviation professionals responsible for overseeing flight training operations during nighttime hours. They supervise flight instructors, ensure compliance with safety regulations, and manage the training curriculum for student pilots. Their role includes conducting flight and ground training, evaluating instructor performance, and addressing any issues that arise during overnight shifts. This position is vital for flight schools that operate around the clock and need consistent leadership and oversight at all hours.

What are some unique challenges faced by an overnight chief flight instructor, and how can they be addressed?

Overnight Chief Flight Instructors often manage flight training operations during non-traditional hours, which presents unique challenges such as ensuring student and instructor alertness, maintaining effective communication with day-shift staff, and addressing limited access to certain resources or support services. Proactive scheduling, thorough shift handovers, and clear documentation are essential to ensure training continuity and student safety. Building a strong overnight team culture and leveraging technology for updates and coordination can also help create a safe and productive learning environment.

What are the key skills and qualifications needed to thrive as an overnight chief flight instructor, and why are they important?

To thrive as an Overnight Chief Flight Instructor, you need an advanced pilot certification (such as a Certified Flight Instructor - Instrument or Multi-Engine), significant instructional experience, and in-depth knowledge of aviation regulations. Familiarity with flight planning software, safety management systems, and aircraft-specific training platforms is typically required. Leadership, strong communication, and decision-making skills are crucial for effectively managing instructors and ensuring student safety during nighttime operations. These abilities are vital to uphold regulatory compliance, maintain training standards, and ensure safe, efficient overnight flight instruction.

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:

Overnight Chief Flight Instructor jobs near you

Chief Flight Instructor

Eagle Aircraft

Chicago, IL • On-site

$83K - $104K/yr

Full-time

Medical

Posted 29 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.