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Freelance Second In Command Pilot Jobs in Chicago, IL

Position Summary The Second in Command (SIC) reports directly to the Base Chief Pilot. The SIC prepares and ensures the safe and efficient operation of company aircraft in accordance with the Federal ...

Position Summary The Second in Command (SIC) reports directly to the Base Chief Pilot. The SIC preparesand ensuresthe safe and efficient operation of company aircraft in accordance with the Federal ...

SIC- Gulfstream G200

Wheeling, IL ยท On-site

$124K - $160K/yr

Position Summary The Second in Command (SIC) reports directly to the Base Chief Pilot. The SIC prepares and ensures the safe and efficient operation of company aircraft in accordance with the Federal ...

SIC- Gulfstream G200

Wheeling, IL ยท On-site

$124K - $160K/yr

Position Summary The Second in Command (SIC) reports directly to the Base Chief Pilot. The SIC prepares and ensures the safe and efficient operation of company aircraft in accordance with the Federal ...

Purpose of Position Executive Jet Management, a Berkshire Hathaway company, is hiring for a Pilot in Command position in support of a Gulfstream G450 based just outside of Chicagoland in Gary, IN at ...

Pilot in Command Falcon 7X

West Chicago, IL ยท On-site

$160K - $275K/yr

Pilot in Command: 2000 hours * PIC MEL: 500 hours * Instrument: 300 hours * Jet: 500 hours Base Salary Range Cabin Size Small/Mid/Supermid $160,000 - $275,000 Large/Heavy/Premium $200,000 - $325,000 ...

As an Assistant Restaurant Manager, you are second in command of a $1 million+ business. Working with your Restaurant General Manager, you grow the business by making our customers' day. And when you ...

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Freelance Second In Command Pilot information

See Chicago, IL salary details

$9

$23

$71

How much do freelance second in command pilot jobs pay per hour?

As of Jul 27, 2026, the average hourly pay for freelance second in command pilot in Chicago, IL is $23.66, according to ZipRecruiter salary data. Most workers in this role earn between $19.33 and $19.33 per hour, depending on experience, location, and employer.

What is a Freelance Second In Command Pilot?

A Freelance Second In Command (SIC) Pilot is a licensed aviator who assists the Captain (or Pilot in Command) during flights, but is not permanently employed by a single airline or operator. Instead, they work on a contract or per-flight basis for various companies or individuals. Their responsibilities include supporting the Captain in flying the aircraft, monitoring instruments, managing communications, and ensuring flight safety. Freelance SIC pilots often work in business aviation, charter operations, or on-demand flight services, and their schedules can be highly flexible. This role requires proper certifications and adherence to aviation regulations.

What are the key skills and qualifications needed to thrive as a Freelance Second In Command Pilot, and why are they important?

To thrive as a Freelance Second In Command Pilot, you need a valid commercial pilot license with multi-engine and instrument ratings, strong aviation knowledge, and flight experience in the relevant aircraft type. Familiarity with flight management systems, navigation tools, and compliance with FAA regulations is essential, along with recurrent training and type ratings as required. Excellent situational awareness, teamwork, and communication skills help ensure smooth coordination with the captain and crew. These skills and qualifications are critical for maintaining safety, regulatory compliance, and effective flight operations in a dynamic aviation environment.

What are the most common challenges faced by a Freelance Second In Command Pilot, and how can they be addressed?

Freelance Second In Command Pilots often face challenges such as adapting quickly to different aircraft, flight crews, and company procedures, since each assignment may involve a new operator. Building rapport with captains and integrating into unfamiliar teams efficiently is essential for safe and effective operations. Staying current with various aircraft systems and maintaining required certifications can also be demanding, so ongoing self-study and recurrent training are crucial. Networking with operators and maintaining a reputation for professionalism can help secure consistent work and career advancement.

What is the difference between Freelance Second In Command Pilot vs Freelance First In Command Pilot?

AspectFreelance Second In Command PilotFreelance First In Command Pilot
CertificationsCommercial Pilot License (CPL), Second Class or Airline Transport Pilot License (ATPL)Commercial Pilot License (CPL), Airline Transport Pilot License (ATPL)
Work EnvironmentAssisting the captain, flying under supervision, in various aircraft typesLeading flights, making final decisions, overall flight responsibility
Employer & Industry UsageCharter companies, private operators, aerial toursAirlines, private charters, corporate flight services

In summary, the Freelance Second In Command Pilot assists the lead pilot and operates under supervision, while the Freelance First In Command Pilot holds the primary responsibility for flight safety and decision-making. Both roles require similar certifications but differ in authority and responsibilities during flights.

What are the most commonly searched types of Second In Command Pilot jobs in Chicago, IL? The most popular types of Second In Command Pilot jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Freelance Second In Command Pilot jobs? Cities near Chicago, IL with the most Freelance Second In Command Pilot job openings:

Pilot Second in Command Falcon 6X

NetJets & EJM

Wheeling, IL โ€ข On-site

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 26 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 (EJM), a Berkshire Hathaway company, is seeking a qualified Second in Command (SIC) to join a Falcon 6X flight department based in Chicago, Illinois (KPWK). This is a unique opportunity to fly one of the newest and most advanced business aircraft in the industry while supporting an established account.
This three-pilot account, supported by a dedicated Maintenance Technician, operates under both Part 91 and Part 135 regulations and offers a dynamic mix of domestic and international flying.
The SIC is responsible for supporting the safe, efficient, and professional operation of all flight assignments while ensuring an exceptional passenger experience. The successful candidate will demonstrate a commitment to safety, operational excellence, and superior customer service.
Tasks and Responsibilities
  • Perform pilot duties in accordance with the Company GOM, FAA Regulations, Operations Specifications, Flight Manuals, etc., and other instructions pertinent to their duties. Responsible for assuring that the company's goals for safety, security and quality are met by continual compliance with the company Safety management System (SMS) program and reporting through the appropriate process any safety, security or quality recommendations or non-compliance observations.
  • Responsible for the post-flight of the aircraft interior, to include, but not limited to, removal of all debris from the cockpit area, removal of ice, coffee, and catering from the aircraft and reporting any interior equipment discrepancies to the PIC.
  • Arrange and obtain cabin items including catering required for a flight as identified by the Flight Operations Center. Provide the highest level of customer service at all times.
  • Coordinate all work schedules and schedule changes with the Chief Pilot. Log and report flight and duty times. Report all commercial flying performed outside the Company to the Flight Operations Center for inclusion in the Flight and Duty Time Records.
  • Maintain and provide the Flight Operations Training Department with a copy of his/her First Class Medical Certificate by the twentieth (20th) of the month due.

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)
Knowledge, Skills, Abilities and Other (KSAOs)
  • Strong prioritizing and organizational skills with the ability to handle multiple & high level priorities
  • Proactive decision making skills
  • Must maintain a valid Medical certificate
  • Will be required to obtain a FAA Type rating in the applicable Fleet type
  • Upholds a service standard in a strict & changing regulatory environment
  • Strong customer service skills
  • Minimum Requirements:
    • Total flight time: 2500 hours
    • Multi Engine Land (MEL): 500 hours
    • Pilot in Command: 500 hours
    • Instrument: 150 hours
    • Jet: 250 hours
    • Turbine Engine: 100 hours
    • Time in Type: 50 hours
  • Preference given to local candidates with a Falcon rating and similar aircraft size experience.

Base Salary Range
The salary range will vary based on experience. The range for a large/heavy cabin aircraft is $125,000 to $325,000.
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
  • 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.