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How to Become a Flight Instructor

How to Become a Flight Instructor at Windy City Flyers

Windy City Flyers maintains a strong, long-standing tradition of providing its customers with exceptional flight instructors. Our current group includes three FAA Safety Counselors and five ATPs. The combined flight experience of our staff exceeds 50,000 hours with several individuals possessing more than 3,000 hours each. In addition, every one of our instructors holds at least one advanced instructor rating.

Many instructors are initially drawn to Windy City Flyers because of our outstanding fleet of aircraft. We’ve learned from our staff that their real interest was to associate with other professionals that are equally as dedicated and committed to their work.  Becoming a flight instructor at Windy City Flyers is not an easy task. The varied fleet of aircraft that may have originally attracted them to us in fact, turns out to be one of the greatest ongoing challenges to working here.  In order to teach in our aircraft, an instructor must first become an expert in every system, component and nuance of the aircraft model they will fly.


Windy City Flyers never ceases in its efforts to recruit new instructors because we believe there is always a place for talent in our organization. We regularly attend career days at some of the country’s leading aviation universities in search of the best candidates. The top prospects will be granted an initial phone interview before receiving an invitation to visit our offices to meet in person.

Acceptable candidates begin their day with a written exam followed by an IFR check in one of our simulators. Next, candidates will take a flight with one of our senior instructors in one of our trainer aircraft. Finally, we present them with a scenario-based, situational test that is designed to evaluate their highest levels of learning.

In order to truly evaluate an applicant’s ability perform under pressure, we need to observe them under stress. To have reached this point, candidates must have demonstrated excellent skills and teaching abilities. Once this is demonstrated and the candidate is successful in meeting all criteria, they will then be invited into our indoctrination program.


Once accepted into our program, a qualified candidate must successfully complete a defined set of tasks that is our indoctrination process. Each new hire receives a Employee Handbook, which will be covered thoroughly during the indoctrination classes. Through these classes, they learn the company policies and procedures and then must demonstrate proficiency by passing another written exam. Instructors who complete this stage of the program will then “shadow” our most experienced instructors, observing their training methods and techniques. Here, they get an opportunity to learn the difference between procedures and techniques as they watch our most experienced instructors at work with our customers.

New instructors begin their employment as dispatchers under management’s supervision.  In this position, we can gauge a new hire’s ability to communicate with customers and staff, as well as, discover their personality and people skills. Succeeding at Windy City Flyers requires a lot more than textbook knowledge and flight proficiency!

The typical indoctrination process is 90 days.  Afterwards, each instructor is assigned to a group leader where they will be under constant supervision while they work with students. Every six months they will undergo a line check with our Chief CFI or senior CFI where the new employee will need to not only demonstrate their skills as a pilot, but also their knowledge and skills as teachers.


Not every instructor makes it through this uncompromising indoctrination process.  Only the top candidates are invited to try, but only the very best complete the program. Frankly, that’s the whole point. We take our responsibilities in selecting and training flight instructors seriously because these are the people who will be providing our customers with the knowledge and skills that will help them achieve their goals and keep themselves and our customers safe.

Why Windy City Flyers?

  • We have an extensive variety of aircraft that all instructors have opportunity to fly and train students
  • Glass panel flying in the multiple SR-22’s and C-172’s
  • High altitude flying in the TR-182RG
  • Start off as a flight instructor, advance to check airmen and eventually to charter pilot
  • Take daytrips and sometimes week-long trips with members to various parts in the country
  • Benefit from “real world” flying, travel well outside the Chicago area improving you airmen abilities as a pilot and instructor
  • Instructor take-home pay can exceed $30 hour
  • Annual trip to Oshkosh
  • Annual golf and bowling outings
  • Company softball team

Contact Stewart Kerr at (847) 808-1188..

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