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Entry Level Pilot Jobs in Chicago, IL (NOW HIRING)

Uncrewed Systems Specialist

Itasca, IL · On-site

$55K - $65K/yr

The Uncrewed Systems Specialist will provide technical, piloting, and sales support. This ... Position Type, Expected Hours of Work, and Travel This is a full-time, entry-level position. Days ...

Uncrewed Systems Specialist

Itasca, IL · On-site

$55K - $65K/yr

The Uncrewed Systems Specialist will provide technical, piloting, and sales support. This ... Position Type, Expected Hours of Work, and Travel This is a full-time, entry-level position. Days ...

Uncrewed Systems Specialist

Itasca, IL · On-site

$55K - $65K/yr

The Uncrewed Systems Specialist will provide technical, piloting, and sales support. This ... Position Type, Expected Hours of Work, and Travel This is a full-time, entry-level position. Days ...

The Uncrewed Systems Specialist will provide technical, piloting, and sales support. This ... Position Type, Expected Hours of Work, and Travel This is a full-time, entry-level position. Days ...

Inventory Specialist

Elmhurst, IL · On-site

$21 - $28/hr

... entry-level roles to certified ATP support and beyond. Compensation: * Hourly Pay: $21-$28 ... Update the equipment ordering queue in Sales Pilot Purchasing & Inventory Performance Metrics

Entry Level Pilot information

See Chicago, IL salary details

$51K

$134.9K

$207.1K

How much do entry level pilot jobs pay per year?

As of Aug 2, 2026, the average yearly pay for entry level 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 the key skills and qualifications needed to thrive as an Entry Level Pilot, and why are they important?

To thrive as an Entry Level Pilot, you need a solid understanding of aerodynamics, navigation, and flight operations, typically backed by a commercial pilot’s license and completed flight training hours. Familiarity with aviation software, flight management systems (FMS), and aircraft-specific instrumentation is commonly required. Strong situational awareness, decisive communication, and the ability to remain calm under pressure are crucial soft skills for this role. These competencies ensure safe, efficient flight operations and effective responses to dynamic in-flight situations.

What Does an Entry-Level Pilot Do?

An entry-level pilot has the same responsibilities as any other pilot, which are to ensure that an airplane takes off, travels, and lands safely. In this position, you may work as a copilot or flight engineer in addition to your duties as a pilot, depending on the need of the airline. These duties include checking that all flight instrumentation is working, performing safety and maintenance checks with other airplane technicians, and filing flight route plans. In the air, you ensure that the plane remains in communication with ground control.

What are entry level pilots?

Entry level pilots are individuals who have recently earned their pilot licenses and are beginning their professional aviation careers. They typically hold a commercial pilot certificate and may work in roles such as flight instructors, regional airline first officers, or charter pilots. Entry level pilots are responsible for flying aircraft safely, following regulations, and gaining experience to qualify for more advanced positions. These pilots often use their initial jobs to build flight hours, develop skills, and advance to higher positions within the aviation industry.

What are the typical training and mentorship opportunities available to entry level pilots starting their careers?

Entry level pilots generally undergo structured training programs that combine classroom instruction, simulator sessions, and supervised flight hours. New pilots often work closely with experienced captains and instructors who provide mentorship and guidance during the initial phases of their careers. Many airlines and flight schools also offer ongoing education and recurrent training to ensure pilots remain current with regulations and best practices. This supportive environment helps entry level pilots build confidence, refine their flying skills, and progress toward more advanced roles.

What is the difference between Entry Level Pilot vs Flight Instructor?

AspectEntry Level PilotFlight Instructor
Required CertificationsPrivate Pilot License (PPL), Commercial Pilot License (CPL)Certified Flight Instructor (CFI), CPL
Work EnvironmentAirlines, charter services, cargo carriersFlight schools, training aircraft
Industry UsageEntry-level commercial flying rolesTraining new pilots, gaining flight hours

Entry Level Pilots typically hold PPL and CPL licenses, working in commercial flying roles. Flight Instructors also hold CFI certification and focus on training pilots, often as a stepping stone to higher flying positions. Both roles require similar licenses but differ in work environment and primary responsibilities.

What are the most commonly searched types of Pilot jobs in Chicago, IL? The most popular types of Pilot jobs in Chicago, IL are:
What job categories do people searching Entry Level Pilot jobs in Chicago, IL look for? The top searched job categories for Entry Level Pilot jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Entry Level Pilot jobs? Cities near Chicago, IL with the most Entry Level Pilot job openings:
Infographic showing various Entry Level Pilot job openings in Chicago, IL as of July 2026, with employment types broken down into 86% Full Time, 11% Part Time, 1% Temporary, and 2% Contract. Highlights an 95% Physical, 2% Hybrid, and 3% Remote job distribution, with an average salary of $134,863 per year, or $64.8 per hour.

Videographer & Content Creator (Part-Time)

Path Construction

Arlington Heights, IL

$40 - $70/hr

Part-time

Posted 12 days ago


Job description

Path Construction is seeking a highly skilled Videographer and Content Creator to capture and produce professional video, photography, and cinematic drone footage across our active jobsites and offices nationwide. This role is central to how we tell the story of our people, our projects, and our culture across recruiting, marketing, business development, and social media.

This is not an entry-level content role. We are looking for someone with real production experience who can shoot broadcast-quality video, edit quickly and cleanly, and operate a drone with genuine cinematic skill, including advanced FPV-style flying (navigating tight spaces, moving through structures, dynamic tracking shots). Final products should look like a professional broadcast package, not standard drone content.

A demo reel is required to apply. Applications submitted without one will not be considered.

This is a part-time position, 2 to 3 days per week (approximately 15-30 hours), with schedule flexibility based on project needs. This role will be based primarily in the Chicago area (approximately 60% of work), with travel to Path Construction offices and jobsites outside of Illinois, including Phoenix, Knoxville, Charlotte, and Tampa, required approximately once or twice per month.

About Path Construction

Path Construction is a national general contractor headquartered in Arlington Heights, IL, with offices and projects throughout the United States. Since 2008, we've delivered high-quality construction services across a diverse range of commercial markets while building lasting relationships with our clients, partners, and communities.

At Path, we believe our people are our greatest asset. We are committed to hiring driven, entrepreneurial individuals who want to grow their careers while making a meaningful impact on the projects and communities we serve.

Responsibilities
  • Capture professional video, photography, and cinematic drone footage at active construction jobsites, including advanced FPV-style flying through structures and tight spaces.
  • Film and edit interview-style videos featuring employees, clients, subcontractors, and project teams, including full on-site audio setup (lav mics, boom, sound levels).
  • Develop interview questions and story angles in collaboration with leadership and project teams ahead of each shoot.
  • Produce project highlight videos and reels with a polished, broadcast-quality look and pace.
  • Create engaging content for recruiting, marketing, business development, social media, and the company website.
  • Collaborate with leadership and project teams to identify stories and content opportunities across the company.
  • Edit and deliver high-quality videos quickly while maintaining Path Construction's brand standards.
  • Organize and maintain a library of video, drone footage, photography, and other digital assets.
  • Operate drones safely and in compliance with FAA regulations and all jobsite safety requirements.

Requirements

    • Demo reel required. Must include examples of advanced cinematic drone piloting (including FPV-style flying through tight or complex spaces) and fast, polished video editing. Portfolio should reflect broadcast-level production quality. Applications without a demo reel link will not be reviewed.
    • Active FAA Part 107 Remote Pilot Certificate required.
    • Experience filming, editing, and producing professional video content from concept through final delivery, on a fast turnaround.
    • Proficiency with Adobe Premiere Pro, Final Cut Pro, DaVinci Resolve, Adobe Creative Suite, or similar editing software.
    • Experience with on-site audio production for interviews (mic setup, sound levels, clean audio capture).
    • Strong eye for storytelling, composition, lighting, and visual branding.
    • Strong interpersonal and communication skills, comfortable directing and putting people at ease on camera.
    • Comfortable working independently while managing multiple projects and deadlines.
    • Comfortable working on active commercial construction jobsites and following all company and OSHA safety requirements.
    • Ability to work outdoors in varying weather conditions, walk uneven terrain, climb stairs, and wear required PPE (hard hat, safety vest, safety glasses, steel-toed boots).
    • Experience in construction, architecture, engineering, industrial, or related industries is a plus.
Equipment
    • Path Construction provides standard camera and drone equipment, including DJI drones and professional DSLR photography equipment, along with industry-standard editing software. Candidates must supply their own FPV drone and piloting equipment (goggles, controller, etc.), as this specialized gear is typically personal to the pilot. Candidates who prefer to use their own standard camera or drone equipment in place of Path-provided equipment are also welcome.

Benefits

    • Hourly Compensation: $40.00-$70.00 per hour, based on experience and qualifications.
    • Company cellphone and computer.
    • Financial and Mental Health Support through a third party.
    • Travel and Entertainment Discount Program.

Path Construction is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive workplace for all employees.