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Live In Retired Pilot Jobs in Chicago, IL (NOW HIRING)

W S Darley & Co

Uncrewed Systems Specialist

Itasca, IL · On-site

$55K - $65K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

In addition to providing prompt technical support and ensuring smooth system performance, this role also supports live demonstrations as a drone pilot, showcasing system capabilities to customers and ...

W S DARLEY & CO

Uncrewed Systems Specialist

Itasca, IL · On-site

$55K - $65K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

In addition to providing prompt technical support and ensuring smooth system performance, this role also supports live demonstrations as a drone pilot, showcasing system capabilities to customers and ...

W S DARLEY & CO

Uncrewed Systems Specialist

Itasca, IL · On-site

$55K - $65K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

In addition to providing prompt technical support and ensuring smooth system performance, this role also supports live demonstrations as a drone pilot, showcasing system capabilities to customers and ...

W S DARLEY & CO

Uncrewed Systems Specialist

Itasca, IL

$55K - $65K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

In addition to providing prompt technical support and ensuring smooth system performance, this role also supports live demonstrations as a drone pilot, showcasing system capabilities to customers and ...

Allegion

Sales Consultant - Integrator - Chicago, IL

Itasca, IL · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

... pilot installs, on-site and virtual product training, and tradeshows are all common activities ... Ideal candidate will live in Greater Chicago, IL and travel within the territory - Chicago and ...

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Showing results 1-20

All JobsLive In Retired Pilot JobsLive In Retired Pilot Jobs in Chicago, IL

Live In Retired Pilot information

See Chicago, IL salary details

$51K

$134.9K

$207.1K

How much do live in retired pilot jobs pay per year?

As of Aug 15, 2026, the average yearly pay for live in retired pilot in Chicago, IL is $134,863.00, according to ZipRecruiter salary data. Most workers in this role earn between $103,000.00 and $159,700.00 per year, depending on experience, location, and employer.

What are some common daily responsibilities for a live in retired pilot?

A Live In Retired Pilot often assists with aviation-related consultations, such as reviewing flight plans, providing mentorship to active pilots, or managing private aircraft operations for the household. Additionally, they may handle logistical arrangements for travel, oversee hangar maintenance, and ensure regulatory compliance for the aircraft. This role typically involves close collaboration with household staff, aviation professionals, and sometimes family members, providing both advisory expertise and practical support as needed.

What is a live in retired pilot?

A Live In Retired Pilot is a former professional pilot who resides at a specific location, often as part of a mutually beneficial arrangement. They may provide occasional aviation expertise, mentorship, or security while enjoying housing and possibly other amenities. This role does not typically involve active flying but rather leverages the pilot's experience in advisory, supervisory, or support capacities. The arrangement can vary widely depending on the needs of the employer and the pilot's background.

What are the key skills and qualifications needed to thrive as a live in retired pilot, and why are they important?

To thrive as a Live In Retired Pilot, you need an extensive background in aviation, a valid or previously held commercial or airline transport pilot license, and a thorough understanding of flight operations. Familiarity with flight planning software, navigation systems, and aviation safety protocols is typically expected. Strong communication, reliability, and adaptability are important soft skills, especially when assisting with private travel, advising on aviation matters, or supervising flight activities. These skills ensure safe and effective support, trustworthy guidance, and smooth coordination for employers relying on your aviation expertise.

What is the difference between Live In Retired Pilot vs Commercial Pilot?

AspectLive In Retired PilotCommercial Pilot
CredentialsRetirement status, possibly FAA retirement certificationCommercial pilot license, FAA certifications
Work EnvironmentRetired, often living in private or family homes, no active flying dutiesActive flying, airports, aircraft operation
Employer & IndustryPrivate individuals, aviation enthusiasts, or retired pilotsAirlines, charter services, cargo companies

The main difference is that a Live In Retired Pilot is no longer actively flying and is typically retired, whereas a Commercial Pilot is actively employed, flying aircraft for various commercial purposes. The retired pilot may still have aviation credentials but no longer performs flying duties, while the commercial pilot is engaged in ongoing flight operations.

What are the most commonly searched types of Retired Pilot jobs in Chicago, IL?

The most popular types of Retired Pilot jobs in Chicago, IL are:

Live In Retired Pilot jobs near you

VFR Medical Pilot - Sign-on Bonus

Northeast Healthcare Recruitment

Harvey, IL

Full-time

Re-posted 14 days ago

Job description

Sign-on Bonus up to $50,000! VFRMedical Pilot to join our mission-driven team. Operating under CAMTS guidelinesto provide life-saving medical transport services. You will play a vital rolein ensuring safe and efficient patient transport while upholding the higheststandards of safety and professionalism.

Aircraft: AS350 VFR/NVG (Instrument ratingrequired)

Operations: 24-hour operations with day/nightrotation

Compensationand Benefits: Sign-on Bonus up to $50,000. Weoffer a range of competitive pay and benefits packages. This package includesshift bonuses, shift incentives, Annual Safety Bonus, Annual Employee Bonus,and much more!

Location& Schedule: Phoenix Sky Harbor, AZ. 7 & 7 schedule (base schedule day of week may vary, schedulechanges may be required). Must live within a 1-hour commute from the base.

AdditionalInformation: Relocationpackage available with a 2-year minimum service requirement per CBA ifutilized. If an aircraft transition is required, a 1-year minimum servicerequirement per CBA applies. Housing is not provided.

Requirements:

  • Commercialand Instrument Helicopter Ratings
  • FirstClass Medical
  • CAMTSRequirement // 2,000 Total Hours // 1,500 Hours Helicopter // 1,000 Hours PICHelicopters // 500 Hours Turbine Helicopters // 100 Hours in Unaided NightOperations or 50 Hours Unaided and 100 Hours Night Vision Goggles (NVG)
  • Candidatesmust meet 235 pounds body weight
  • StrongCommunication, Internal and External Customer Service Skills
  • Interviewand acceptance by customer and management
  • AnnualFlu Vaccine not required
  • Mustbe able to pass pre-placement physical exam including functional capacity exam(strength and flexibility assessment, lift 100 pounds to assist in the loadingand unloading of patients and equipment.), drug screening and backgroundscreen.
  • DemonstratedInternal and External Customer Service skills
  • Excellentverbal and written communication skills
Northeast Healthcare Recruitment logo

About Northeast Healthcare Recruitment

Sourced by ZipRecruiter

Northeast Healthcare Recruitment (NEHCR) is a leader in the healthcare recruitment industry and is based in Plymouth, MA, US. With an established online presence through nehcr.com, the company provides a variety of recruiting solutions in the healthcare sector. Since its inception, the mission of NEHCR has been to help better the lives of others by matching the best healthcare professionals with the right opportunities. They leverage their expertise and vast network to connect healthcare providers with facilities needing these specialized skills.

Industry

Health care and social assistance

Company size

11 - 50 Employees

Headquarters location

Plymouth, MA, US

Year founded

2011

Social media

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