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Weekend Part 135 Pilot Jobs in Chicago, IL (NOW HIRING)

Maintenance Controller

Wheeling, IL · On-site +1

$85K - $90K/yr

Our team operates in a dynamic Part 135 and Part 91 environment, supporting diverse aircraft types ... Other: * Ability to work weekends. This is an exempt position which requires flexibility to meet ...

Must be available to work on any day, seven days a week, including nights, weekends and holidays ... SkyWest will accept helo/glider time as part of an applicant's total time as long as they have a ...

This is a three-pilot account supported by a dedicated Maintenance Technician flying part 91 and 135 to domestic and international destinations. This is not a commutable position and will require ...

... Part 91 and 135 flight operations. It is expected that the candidate lives, or be willing to ... Pilot * Ability to work nights, weekends, and holidays * Bachelor's degree or equivalent work ...

SIC- Gulfstream G200

Wheeling, IL · On-site

$124K - $160K/yr

... Part 91 and 135 flight operations. It is expected that the candidate lives, or be willing to ... Pilot * Ability to work nights, weekends, and holidays * Bachelor's degree or equivalent work ...

SIC- Gulfstream G200

Wheeling, IL · On-site

$124K - $160K/yr

... Part 91 and 135 flight operations. It is expected that the candidate lives, or be willing to ... Pilot * Ability to work nights, weekends, and holidays * Bachelor's degree or equivalent work ...

SIC- Gulfstream G200

Wheeling, IL · On-site

$124K - $160K/yr

... Part 91 and 135 flight operations. It is expected that the candidate lives, or be willing to ... Pilot * Ability to work nights, weekends, and holidays * Bachelor's degree or equivalent work ...

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Showing results 1-20

Weekend Part 135 Pilot information

See Chicago, IL salary details

$51K

$134.9K

$207.1K

How much do weekend part 135 pilot jobs pay per year?

As of Aug 26, 2026, the average yearly pay for weekend part 135 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 is the difference between Weekend Part 135 Pilot vs Part 91 Pilot?

AspectWeekend Part 135 PilotPart 91 Pilot
CertificationsCommercial Pilot Certificate, specific Part 135 trainingCommercial Pilot Certificate, general flying experience
Work EnvironmentCharter flights, on-demand services, often weekendsPrivate, corporate, or recreational flying, flexible schedule
Employer & IndustryPart 135 charter operators, air taxi servicesPrivate aircraft owners, corporate flight departments

Weekend Part 135 Pilots typically operate charter and air taxi flights under Part 135 regulations, often on weekends or irregular hours. In contrast, Part 91 Pilots generally fly private or corporate aircraft with more flexible schedules. Both roles require similar certifications but differ mainly in work environment and operational scope.

What are the most commonly searched types of Part 135 Pilot jobs in Chicago, IL?

The most popular types of Part 135 Pilot jobs in Chicago, IL are:

What are popular job titles related to Weekend Part 135 Pilot jobs in Chicago, IL?

For Weekend Part 135 Pilot jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Weekend Part 135 Pilot jobs in Chicago, IL look for?

The top searched job categories for Weekend Part 135 Pilot jobs in Chicago, IL are:

Infographic showing various Weekend Part 135 Pilot job openings in Chicago, IL as of August 2026, with employment types broken down into 33% Full Time, and 67% Part Time. Highlights an 100% In-person job distribution, with an average salary of $134,863 per year, or $64.8 per hour.

Pilot in Command Challenger 300 (Chicago)

Chicago, IL • On-site

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 24 days ago


Job description

About EJM

EJM has been a pioneer in aircraft management and worldwide jet charter services since 1977. As a subsidiary of NetJets, we are part of the world's largest private aviation infrastructure, with unrivaled resources and operational stability. Our business is rooted in the core principles of safety, service, and integrity—principles that we deliver on daily for our customers and employees.

Purpose of Position

Executive Jet Management, a Berkshire Hathaway company, is seeking qualified Pilot in Command candidates for a Challenger CL300 aircraft based in Chicago IL at MDW airport. This is a three - pilot account supported by a dedicated Maintenance Technician flying owner part 135 and part 91. Flying is mostly domestic with a few international trips annually to the Caribbean and Mexico for an average of 200 hours of total annual flying.

This position is not commutable and will require residing within a one-hour driving distance to MDW airport.

Tasks and ResponsibilitiesEnsures the Safe Operation of Flight:
  • Ensures crewing and trip assignments are compliant with company and regulatory requirements.
  • Completes flight planning, performance and weight and balance tasks for each assignment, as required.
  • Utilizes Threats, Plans and Considerations (TPC) briefing methodology to lead required briefings and mitigate operational risks.
  • Complies with company Standard Operating Procedures (SOPs) and coordinates with company personnel as required. Acts as the Grounds Security and In-Flight Security Coordinator as defined by company policy.
  • Completes all aircraft pre-flight tasks, including the maintenance status of the aircraft, to ensure the aircraft is mission capable. Records all aircraft discrepancies in accordance with company SOPs.
  • Ensures all aircraft ground servicing items (e.g., fueling, oil, oxygen) are monitored and accomplished in accordance with SOPs.
  • Completes passenger briefings in accordance with company policy and regulation. Delivers the highest level of customer service and meet any special needs of passengers (e.g., physically challenged).
  • Utilizes Crew Resource Management (CRM) and Threat and Error Management (TEM) to communicate with crew and support personnel clearly and in a timely manner during normal, abnormal, and emergency operations.
Delivers an Exceptional Service Experience:
  • Provides quality service to owners and passengers while identifying opportunities to enhance the EJM service experience. Regularly investigates and resolves service deviations.
  • Collaborates with fellow crew members and EJM internal partners to provide consistent service experience to owners and passengers. Resolves conflict and challenges in an acceptable manner.
Maintains Proficiency and Compliance:
  • Maintains regulatory and company-required training and recency of experience.
  • Complies with company SMS program and reports safety or non-compliance concerns through the appropriate channels.
Note:

It is not possible to list all required job duties on this form. There may be other important duties assigned, depending on the position. For a list of essential job functions, please refer to the essential functions document for this job.

Certifications and Licenses
  • FAA Airline Transport Pilot (ATP)
  • First Class Medical Certificate
Years of Experience

4-6 years of experience

Knowledge, Skills, Abilities and Other (KSAOs)
  • Prior experience in corporate/business aviation preferred
  • FAA Type rating in applicable fleet
  • Must be able to perform the essential functions of the position
Minimum Time Requirements
  • Total flight time: 3500 hours
  • Multi Engine Land (MEL): 1500 hours
  • Pilot in Command: 2000 hours
  • PIC MEL: 500 hours
  • Instrument: 300 hours
  • Jet: 500 hours
How EJM Supports You

At EJM, we believe that how you do something is as important as what you do. That's why we foster a collaborative company culture, where leadership is accessible, employee opinions are valued, and relationships matter. We encourage employee growth, recognize the importance of work-life balance, and take pride in being a career destination.

To ensure our employees are taken care of at work and at home, we offer a comprehensive package of premium benefits, including:

  • Competitive pay
  • Medical, dental, and vision insurance, available with no monthly premiums
  • 401(k) plan, with 67% of every dollar you contribute matched by EJM
  • Health savings account (HSA)
  • Flexible spending accounts (FSA)
  • Prescription drug benefit plan
  • Life insurance and AD&D benefits
  • Short-term disability
  • Long-term disability
  • Loss of license coverage
  • Paid Parental Leave
  • Pet insurance
  • 14 days of paid time off, available on first day of employment

Executive Jet Management is an equal opportunity employer.

To ensure a safe environment, we conduct pre-employment drug screening and background checks.

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