Pilot Jobs in Chicago, IL

New Pilot Jobs with salaries & benefits from top venues every day

Looking for Pilot jobs in Chicago, IL close to you? You're in the right place. Browse current openings and apply today to take the next step in your hospitality career.

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Top Paying Pilot Jobs in Chicago, IL

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Explore 31 Pilot Jobs - Updated Oct 30, 2025

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From $15.00 to $20.53

From $15.00 to $20.53

Hourly

Hourly

Hourly

Hourly

Full-time

Full-time

Part-time

Part-time

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Pilot Company is a leading network of travel centers operating over 750 retail and fueling locations across 44 states in the U.S. and six Canadian provinces. Founded in 1958 by Jim A. Haslam II and currently...

Posted 1 day ago

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From $15.00 to $20.53

From $15.00 to $20.53

Hourly

Hourly

Hourly

Hourly

Part-time

Part-time

Flexible

Flexible

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Pilot Company is a leading network of travel centers operating across 44 states in the United States and six Canadian provinces. Established in 1958 by Jim A. Haslam II and led today by CEO Adam Wright, the...

Posted 1 day ago

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From $40,001.00 to $80,000.00

From $40,001.00 to $80,000.00

Salary

Salary

Part-time

Part-time

Day Shifts

Day Shifts

Expert Level (7+ years)

Expert Level (7+ years)

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SAIC (Science Applications International Corporation) is a premier technology integrator providing full lifecycle services and solutions in the technical, engineering, intelligence, and enterprise information...

Posted 5 days ago

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From $87,019.00 to $95,720.00

From $87,019.00 to $95,720.00

Salary

Salary

Full-time

Full-time

Standard Hours

Standard Hours

Expert Level (7+ years)

Expert Level (7+ years)

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Global Medical Response (GMR) is a leading provider of emergency medical services committed to delivering compassionate and high-quality patient care worldwide. Specializing in emergency medical transportation...

Posted 8 days ago

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From $64,885.00 to $84,514.00

From $64,885.00 to $84,514.00

Salary

Salary

Full-time

Full-time

Standard Hours

Standard Hours

Entry Level (1-2 years)

Entry Level (1-2 years)

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United Airlines is a leading global airline committed to connecting people and uniting the world safely, reliably, and efficiently each day. As one of the largest and most respected airlines in the industry,...

Posted 17 days ago

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From $62,300.00 to $90,700.00

From $62,300.00 to $90,700.00

Salary

Salary

Full-time

Full-time

Standard Hours

Standard Hours

Entry Level (1-2 years)

Entry Level (1-2 years)

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United Airlines is a major American airline known for providing comprehensive air travel services across domestic and international routes. As one of the world's largest and most recognized airlines, United...

Posted 19 days ago

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From $64,885.00 to $84,514.00

From $64,885.00 to $84,514.00

Salary

Salary

Full-time

Full-time

Standard Hours

Standard Hours

Entry Level (1-2 years)

Entry Level (1-2 years)

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United Airlines is a leading global airline headquartered in the United States. Established as one of the world's largest airlines, United Airlines operates an extensive route network connecting numerous...

Posted 20 days ago

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Full-time

Full-time

Expert Level (7+ years)

Expert Level (7+ years)

Health Insurance

Health Insurance

Dental Insurance

Dental Insurance

Paid Time Off

Paid Time Off

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Solairus Aviation is a distinguished leader in the aviation industry, renowned for delivering exceptional private jet charter services and aircraft management solutions. The company prides itself on fostering...

Posted 23 days ago

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From $260,000.00 to $265,000.00

From $260,000.00 to $265,000.00

Salary

Salary

Full-time

Full-time

Flexible

Flexible

Expert Level (7+ years)

Expert Level (7+ years)

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Our client is a distinguished leader in the private aviation sector, recognized for their commitment to excellence, safety, and innovation. Operating a modern fleet of four state-of-the-art aircraft, including...

Posted 23 days ago

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From $133,251.00 to $133,251.00

From $133,251.00 to $133,251.00

Salary

Salary

Full-time

Full-time

Standard Hours

Standard Hours

Mid Level (3-7 years)

Mid Level (3-7 years)

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Air Methods is a leading provider of air medical transport services, operating a fleet of helicopters and fixed-wing aircraft to deliver critical care and rapid transport for patients in emergency situations....

Posted about 1 month ago

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31 Pilot Jobs in Chicago, IL Near You - October 2025

If you're looking for Pilot jobs in Chicago, you're in the right place. The city's transportation and aviation sectors are thriving, and OysterLink currently lists 31 Pilot positions near you across airlines, private aviation companies, corporate fleets, and more in the area.

New job listings are added any time an employer posts a job, and companies are hiring immediately to fill high-demand roles such as Pilots.

Recent Openings for Pilots in Chicago, IL

There have been 2 new jobs posted in the last 10 days, but more get added each day, allowing you to find verified, up-to-date opportunities to work as a Pilot in Chicago.

Pilot Salary in Chicago, IL

From the job listings we have, the average salary for Pilots in Chicago is $97,200 per year or $46.8 per hour, reflecting experience, certification levels, and type of aviation.

Job listings fall within a range between $31,200 per year and $265,000 per year, depending on factors such as flight hours, employer, and aircraft type.

Lowest wage for Pilots in ChicagoAverage wage for Pilots in ChicagoHighest wage for Pilots in Chicago
$31,200 per year$97,200 per year or $46.8 per hour$265,000 per year

Experienced Pilots flying for major airlines or private charters generally earn higher compensation and additional benefits.

Chicago’s status as a transportation hub means Pilot jobs here can offer competitive pay along with opportunities for advancement.

If you're considering Pilot jobs in Chicago, expect a dynamic career with varied flight assignments and the potential to grow your skills.

How To Apply for Pilot Jobs in Chicago, IL

Applying for jobs is straightforward with OysterLink. Every listing is verified and includes clear info about pay, schedules, employer type, and required qualifications. You can filter jobs by:

  • Pay rate
  • Experience level
  • Full-time, part-time, or seasonal
  • Shift availability

Employers hiring for Pilot roles in Chicago want fast hires, so early applications can make a big difference.

Simply click apply, upload your information, and connect directly with hiring managers.

Why Pilot Jobs Are in Demand in Chicago

Chicago is a major aviation center, hosting large airports that generate a consistent need for Pilots.

Here are areas and establishments where Pilots are in high demand in Chicago:

NeighborhoodsEstablishments
O'Hare International AirportMajor airline hubs
Midway AirportRegional flight operators
Chicago Executive AirportPrivate aviation and charter companies

Chicago’s strategic location and large passenger traffic keep demand steady for skilled Pilots, with opportunities in commercial, cargo, and private sectors.

Where Pilots Are in Demand in Chicago

Here's a list of just a few employers where Pilots are sought after in Chicago:

  • Total Aviation Staffing, LLC
  • DRW
  • Executive Jet Management

What To Expect as a Pilot in Chicago

Pilot jobs in Chicago typically involve:

  • Operating aircraft safely and efficiently
  • Conducting pre-flight inspections and briefings
  • Communicating with air traffic control
  • Monitoring weather conditions and flight instrumentation

Many employers also expect Pilots to maintain detailed flight logs, adhere to safety protocols, and coordinate with crew members.

The work requires excellent decision-making, situational awareness, and adherence to regulatory requirements.

While experience is highly valued, there are opportunities for new Pilots with appropriate certifications and licenses.

Pilot Job Benefits and Perks in Chicago

Many Pilot roles in Chicago come with added benefits. Aside from competitive salaries, employers often offer Professionaldevelopment, Internationaldestinations, and much more.

If you're looking for Pilot positions that go beyond just a paycheck, Chicago employers provide incentives to attract and retain top talent.

Explore More Pilot Opportunities Near Chicago

Chicago is just one hub of aviation hiring. You can also find Pilot jobs in nearby cities such as:

  • Naperville
  • Evanston
  • Schaumburg

Some offer different flight routes, schedules, or employer types.

Whether you're looking for Pilot jobs near you, or want to explore the broader Chicago aviation scene, OysterLink helps you find reliable, real-time listings from popular and verified employers.

Useful Resources for Pilots in Chicago, IL

Here are some useful resources if you're a Pilot in Chicago:

ResourceDescription
Federal Aviation Administration (FAA)National aviation authority and pilot certification
Illinois Department of Transportation (IDOT)Transportation oversight including aviation services
City of Chicago Official WebsiteLocal services and aviation-related employment