49 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 49 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 9 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 $82,000 per year or $39.4 per hour, reflecting experience, certification levels, and type of aviation.
Job listings fall within a range between $29,100 per year and $250,000 per year, depending on factors such as flight hours, employer, and aircraft type.
| Lowest wage for Pilots in Chicago | Average wage for Pilots in Chicago | Highest wage for Pilots in Chicago |
|---|---|---|
| $29,100 per year | $82,000 per year or $39.4 per hour | $250,000 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:
| Neighborhoods | Establishments |
|---|---|
| O'Hare International Airport | Major airline hubs |
| Midway Airport | Regional flight operators |
| Chicago Executive Airport | Private 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:
- DRW
- Trekker
- 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 Commuter Benefits, Retirement Plan, 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:
| Resource | Description |
|---|---|
| Federal Aviation Administration (FAA) | National aviation authority and pilot certification |
| Illinois Department of Transportation (IDOT) | Transportation oversight including aviation services |
| City of Chicago Official Website | Local services and aviation-related employment |