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Independent Contractor Pilot Jobs in Chicago, IL

Diageo

Beverage Tech Development

Plainfield, IL · On-site

$47K - $64K/yr

TDT contractors are given real responsibilities and challenges with projects that have an immediate ... Lead liquid processing or fermentation / distillation optimization (laboratory scale to pilot or ...

DIAGEO PLC

Beverage Tech Development

Plainfield, IL · On-site

$47K - $64K/yr

TDT contractors are given real responsibilities and challenges with projects that have an immediate ... Lead liquid processing or fermentation / distillation optimization (laboratory scale to pilot or ...

Aquestive Therapeutics

Process Engineer

Portage, IN · On-site

Determines process parameters at Pilot and Commercial Scale. * Evaluates process parameter ... Work with and manage outside contractors to provide support to projects. * Able to perform all ...

Epsteinglobal

BIM Specialist

Chicago, IL · On-site

$65 - $80/hr

Support pilot testing and implementation of new BIM tools and add-ins * Train team members on BIM ... Self‑motivated with the ability to work independently and within multidisciplinary team * Takes ...

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All JobsIndependent Contractor Pilot JobsIndependent Contractor Pilot Jobs in Chicago, IL

Independent Contractor Pilot information

See Chicago, IL salary details

$51K

$135K

$207.2K

How much do independent contractor pilot jobs pay per year?

As of Sep 5, 2026, the average yearly pay for independent contractor pilot in Chicago, IL is $134,969.00, according to ZipRecruiter salary data. Most workers in this role earn between $103,100.00 and $159,800.00 per year, depending on experience, location, and employer.

What is an independent contractor pilot?

An Independent Contractor Pilot is a professional aviator who operates aircraft on a contract basis rather than as a direct employee of an airline or company. These pilots are typically hired for specific flights, short-term assignments, or ongoing freelance work. They may fly private jets, charter planes, cargo aircraft, or corporate flights, depending on their qualifications and experience. Independent Contractor Pilots must manage their own schedules, maintain necessary certifications, and ensure compliance with aviation regulations.

What are the key skills and qualifications needed to thrive as an independent contractor pilot?

To thrive as an Independent Contractor Pilot, you need a valid commercial pilot’s license, extensive flight experience, and strong knowledge of aviation regulations. Proficiency with navigation systems, flight planning software, and safety management systems is typically required, along with up-to-date certifications such as an FAA medical certificate. Outstanding situational awareness, problem-solving skills, and the ability to communicate clearly with clients and aviation professionals are essential soft skills. These abilities ensure safe, efficient, and client-focused operations in a dynamic and self-directed professional environment.

What are some of the unique challenges faced by independent contractor pilots compared to full-time airline pilots?

Independent Contractor Pilots often manage their own schedules, contracts, and travel logistics, which can require significant self-organization and flexibility. Unlike airline pilots with set routes and support teams, contractor pilots may fly a variety of aircraft for different clients, adapting quickly to new procedures and work environments. They are also responsible for maintaining their own credentials, insurance, and compliance with all regulatory requirements. This autonomy provides greater freedom but also requires a proactive approach to time management, professional networking, and personal safety.

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 are popular job titles related to Independent Contractor Pilot jobs in Chicago, IL?

For Independent Contractor Pilot jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Independent Contractor Pilot jobs in Chicago, IL look for?

The top searched job categories for Independent Contractor Pilot jobs in Chicago, IL are:

Independent Contractor Pilot jobs near you
Infographic showing various Independent Contractor Pilot job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 18% Part Time, and 7% Contract. Highlights an 92% Physical, 2% Hybrid, and 6% Remote job distribution, with an average salary of $134,969 per year, or $64.9 per hour.

Customer Engagement Specialist - Digital Health Startup

Verity Technologies

Downers Grove, IL • On-site

$50K - $65K/yr

Full-time

Re-posted 10 days ago

Job description

Location: Midwest (field-based, daily travel between client sites)
Compensation: $45,000–$60,000 base salary + mileage reimbursement + bonus opportunity
Employment Type: Full-time, independent contractor
About Verity XR:
Verity XR is a healthcare technology company using immersive XR software to transform physical rehabilitation. Our platform helps clinicians engage patients more effectively, track performance, and deliver modern, data-driven rehab.
We work closely with physical therapists, physicians, and healthcare organizations to improve outcomes, adherence, and patient experience.
Role Overview:
We are seeking a Customer Engagement Specialist who will be the primary point of contact for our clinical customers. This role sits at the intersection of customer success, clinical education, and light sales support.
You’ll be responsible for ensuring our customers are trained, engaged, and successful using Verity XR—while also helping introduce the platform to new clinicians and supporting early sales conversations.
This is an in-the-field role, and the right candidate enjoys building relationships, teaching others, and working with technology in real-world clinical settings.
Key Responsibilities:
Customer Success & Engagement:
  • Serve as the primary liaison for assigned clinics and provider partners.
  • Train physical therapists, assistants, and staff on Verity XR software and workflows.
  • Support onboarding of new sites and clinicians.
  • Ensure smooth adoption of new features, updates, and enhancements.
  • Track utilization, engagement, and customer satisfaction.
  • Collect and communicate customer feedback to the product and leadership teams.

Clinical Education & Support:
  • Provide ongoing education to therapists and physicians on clinical use cases and best practices.
  • Help clinicians understand how to integrate Verity XR into existing rehab workflows.
  • Troubleshoot technical or workflow issues and coordinate with internal support as needed.

Sales Enablement (Light):
  • Introduce Verity XR to new therapists, physicians, and clinic staff.
  • Support demos, in-services, and on-site education sessions.
  • Help identify expansion opportunities within existing accounts.
  • Partner with sales leadership to support pilots and early adoption.

Qualifications:
  • Background in rehabilitation or movement science (e.g., PTA, Athletic Trainer, Exercise Science, Rehab Tech, or similar).
  • Comfortable with technology and learning new software platforms.
  • Self-starter with strong communication and teaching skills. 
  • Highly organized and able to manage multiple client sites.
  • Willing and able to travel daily between customer locations.
  • Valid driver’s license.

Nice to Have:
  • Experience working in outpatient physical therapy or orthopedic settings.
  • Experience training clinicians or supporting clinical software adoption.
  • Familiarity with digital health, rehab tech, or RPM/RTM tools.

Why Join Verity XR:
  • Be part of an early-stage, fast-growing health tech company.
  • Direct impact on how clinicians deliver care and how patients recover.
  • Blend of clinical, tech, and relationship-building work.
  • Opportunity to grow into leadership, product, or commercial roles.

Compensation:
  • Base salary: $45,000–$60,000, commensurate with experience.
  • Mileage reimbursement for travel between sites.
  • Opportunity for performance-based bonuses and growth as the company scales.