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Overnight Multi Engine Instructor Jobs in Chicago, IL

Chief Flight Instructor

Chicago, IL ยท On-site

$83K - $104K/yr

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.

Chief Flight Instructor

Chicago, IL ยท On-site

$83K - $104K/yr

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.

FLIGHT INSTRUCTOR

West Chicago, IL ยท On-site

$20 - $28/hr

FAA Class III Medical required Travel Overnight flight or night flights may be required. Physical ... monitor engine operations of functioning, and communicate and coordinate vehicle or aircraft ...

Overnight Multi Engine Instructor information

What are the key skills and qualifications needed to thrive as an Overnight Multi Engine Instructor, and why are they important?

To thrive as an Overnight Multi Engine Instructor, you need a commercial pilot license with multi-engine and instructor ratings, along with strong knowledge of flight operations and safety protocols. Familiarity with flight simulators, aviation training management systems, and FAA regulations is typically required. Outstanding communication, patience, and the ability to adapt teaching methods to individual student needs are valuable soft skills in this role. These qualifications and abilities are crucial for ensuring effective instruction, regulatory compliance, and the safety of both students and aircraft during nighttime operations.

What is the difference between Overnight Multi Engine Instructor vs Multi Engine Flight Instructor?

AspectOvernight Multi Engine InstructorMulti Engine Flight Instructor
Certifications RequiredCommercial Pilot Certificate, Multi-Engine Rating, Certified Flight Instructor (CFI), Multi-Engine Instructor EndorsementCommercial Pilot Certificate, Multi-Engine Rating, Flight Instructor Certificate, Multi-Engine Instructor Endorsement
Work EnvironmentTraining flights, often overnight, in flight schools or training centersFlight training sessions, primarily during daytime or scheduled hours
Employer & Industry UsageFlight schools, training academies, aviation training providersFlight schools, aviation academies, flight training organizations

The main difference between an Overnight Multi Engine Instructor and a Multi Engine Flight Instructor is the work setting. The Overnight Multi Engine Instructor specializes in training students during overnight flights, often requiring additional scheduling and endurance. In contrast, the Multi Engine Flight Instructor typically conducts training during regular hours. Both roles require similar certifications, but the overnight aspect adds unique logistical and operational considerations.

What are some common challenges faced by an Overnight Multi Engine Instructor, and how can they be managed?

Overnight Multi Engine Instructors often face challenges such as adjusting to irregular sleep schedules, maintaining alertness during late-night hours, and ensuring student engagement in a fatigue-prone environment. To manage these, instructors typically prioritize effective time management, adhere to strict sleep routines, and utilize engaging teaching methods tailored to nighttime operations. Collaboration with other instructors and regular communication with the training team also help in sharing best practices and ensuring safety standards are consistently met during overnight shifts.

What does an Overnight Multi Engine Instructor do?

An Overnight Multi Engine Instructor is a certified flight instructor who specializes in teaching pilots how to operate multi-engine aircraft during nighttime or overnight hours. Their responsibilities include providing ground and in-flight instruction, monitoring student performance, and ensuring safety protocols are followed during night operations. These instructors often work with students who have busy daytime schedules or who need to log nighttime flight hours for certification. They must have advanced knowledge of multi-engine systems, night flying techniques, and FAA regulations. Their expertise helps students earn multi-engine and night flight ratings.
What are the most commonly searched types of Multi Engine Instructor jobs in Chicago, IL? The most popular types of Multi Engine Instructor jobs in Chicago, IL are:
Infographic showing various Overnight Multi Engine Instructor job openings in Chicago, IL as of July 2026, with employment types broken down into 20% As Needed, 60% Full Time, and 20% Part Time. Highlights an 100% In-person job distribution.

Chief Flight Instructor

Eagle Aircraft

Chicago, IL โ€ข On-site

$83K - $104K/yr

Full-time

Medical

Posted 9 days ago


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.