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First Pilot Jobs in Chicago, IL (NOW HIRING)

SkyWest Airlines

First Officer Pilot

Chicago, IL

Be at least 21 years of age Hold a Commercial Pilot Certificate with Multi-Engine and Instrument Ratings English Proficiency Endorsement (EPE) on Airman Certificate Hold a current FAA First Class ...

NetJets & EJM

Pilot in Command Falcon 7X

West Chicago, IL · On-site

$160K - $275K/yr

Certifications and Licenses First Class Medical Certificate FAA Airline Transport Pilot (ATP) Years of Experience 4-6 years of experience Knowledge, Skills, Abilities and Other (KSAOs) * Prior ...

Jet Linx Aviation

SIC- Gulfstream G200

Wheeling, IL

Position Summary The Second in Command (SIC) reports directly to the Base Chief Pilot. The SIC ... Maintain a current 1st Class medical certificate * Convey strong, proactive decision-making skills

Jet Linx

SIC- Gulfstream G200

Wheeling, IL · On-site

$124K - $160K/yr

Position Summary The Second in Command (SIC) reports directly to the Base Chief Pilot. The SIC ... Maintain a current 1st Class medical certificate * Convey strong, proactive decision-making skills

Jet Linx Aviation

SIC- Gulfstream G200

Wheeling, IL

$124K - $160K/yr

Position Summary The Second in Command (SIC) reports directly to the Base Chief Pilot. The SIC ... Maintain a current 1st Class medical certificate * Convey strong, proactive decision-making skills

Jet Linx Aviation

SIC- Gulfstream G200

Wheeling, IL · On-site

$124K - $160K/yr

Position Summary The Second in Command (SIC) reports directly to the Base Chief Pilot. The SIC ... Maintain a current 1st Class medical certificate * Convey strong, proactive decision-making skills

Harvey

Legal Engineer (Law Firm, Corporate)

Chicago, IL · On-site

$220K - $320K/yr

They translate real legal work into Harvey solutions, serving as the trust layer across the entire customer lifecycle, from the first pilot to the most complex, custom-built workflow. At Harvey, we ...

Harvey

Legal Engineer (In-House)

Chicago, IL · On-site

$220K - $320K/yr

They translate real legal work into Harvey solutions, serving as the trust layer across the entire customer lifecycle, from the first pilot to the most complex, custom-built workflow. At Harvey, we ...

Pilot Flying J

Travel Center General Manager

Joliet, IL · On-site

$54K - $80K/yr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Food Services Leader

Hebron, IN · On-site

$14.95 - $22.22/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Guest Services Leader

Hebron, IN

$14.95 - $22.22/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Deli Shift Leader

Hebron, IN · On-site

$14.95 - $22.22/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Guest Services Leader

Lake Station, IN · On-site

$14.95 - $22.22/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Guest Services Leader

Hebron, IN

$14.95 - $22.22/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

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Showing results 1-20

All JobsFirst Pilot JobsFirst Pilot Jobs in Chicago, IL

First Pilot information

See Chicago, IL salary details

$51K

$134.9K

$207.1K

How much do first pilot jobs pay per year?

As of Aug 18, 2026, the average yearly pay for first 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 is a first pilot?

First Pilots, also known as captains, are the lead pilots responsible for commanding an aircraft during flights. They oversee all aspects of flight operations, including navigation, communication with air traffic control, and ensuring the safety of passengers and crew. First Pilots have the highest authority on the aircraft and make critical decisions, especially in emergency situations. They are required to have extensive flying experience, advanced training, and must hold an Airline Transport Pilot License (ATPL). Their leadership and expertise are essential for the safe and efficient operation of commercial and cargo flights.

What are the key skills and qualifications needed to thrive as a first pilot?

To thrive as a First Pilot, you need an Airline Transport Pilot License (ATPL), strong aeronautical knowledge, and extensive flight experience. Familiarity with advanced avionics, flight management systems, and regulatory compliance tools is essential. Excellent decision-making, situational awareness, and communication skills set top pilots apart in the cockpit. These skills and qualities are crucial for ensuring passenger safety, efficient flight operations, and effective teamwork in high-pressure environments.

What are some common challenges first pilots face during long-haul flights, and how are these managed on the job?

First Pilots on long-haul flights often face challenges such as fatigue management, maintaining situational awareness over extended periods, and adapting to rapidly changing weather or air traffic conditions. These are managed through regulated rest periods, effective crew resource management, and strict adherence to safety protocols. Collaboration with co-pilots, cabin crew, and air traffic controllers is essential to ensure safe and efficient operations throughout the flight. Continuous training and simulation exercises also help First Pilots stay prepared for unexpected situations.

What is the difference between First Pilot vs Co-Pilot?

AspectFirst PilotCo-Pilot
CertificationsCommercial Pilot License (CPL), Airline Transport Pilot (ATP) certificateCommercial Pilot License (CPL), often with additional type ratings
Work EnvironmentLeads flight operations, makes critical decisions, oversees crewAssists the First Pilot, manages navigation and communication
ResponsibilitiesOverall flight command, safety, and decision-makingSupports the First Pilot, handles specific flight tasks

The First Pilot is the primary authority during flights, responsible for safety and decision-making, while the Co-Pilot assists and supports the First Pilot in operating the aircraft. Both roles require similar certifications, but the First Pilot holds the lead position in flight operations.

What first pilot jobs are best for beginners?

Entry-level pilot jobs suitable for beginners include flight instructor, banner tow pilot, and aerial survey pilot, which often require a private pilot certificate and some flight hours. These roles provide practical experience and help build hours toward commercial pilot certification, with a focus on safety, communication, and aircraft handling skills.

What are popular job titles related to First Pilot jobs in Chicago, IL?

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

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

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

First Pilot jobs near you
Infographic showing various First Pilot job openings in Chicago, IL as of August 2026, with employment types broken down into 86% Full Time, and 14% Part Time. Highlights an 86% In-person, and 14% Remote job distribution, with an average salary of $134,863 per year, or $64.8 per hour.

First Officer Pilot

SkyWest Airlines

Chicago, IL

Full-time

Re-posted 9 days ago

SkyWest Airlines rating

7.1

Company rating: 7.1 out of 10

Based on 80 frontline employees who took The Breakroom Quiz

14th of 26 rated airlines

Job description


Primary Job Duties

To be considered for a pilot position, you must: 

Be at least 21 years of age 
Hold a Commercial Pilot Certificate with Multi-Engine and Instrument Ratings
English Proficiency Endorsement (EPE) on Airman Certificate
Hold a current FAA First Class Medical Certificate
Be a U.S. citizen or able to show proof of right to work in the U.S. 
Hold FCC Radiotelephone Operator's Permit.
Have a current Passport --or other travel documents enabling the bearer to freely exit and re-enter the U.S. (multiple reentry status) and be legally eligible to work in the U.S. (possess proper working documents).
Must be available to work on any day, seven days a week, including nights, weekends and holidays.
Be within three months of the minimum hour requirements detailed below

ATP Written Requirement: 

SkyWest will provide the means to complete a SkyWest-approved CTP course for those who complete an application and successfully pass the pilot interview. 
 

Pilot applicants must meet the experience requirements of FAR 61.159 prior to employment.  

SkyWest Minimum Requirements When Counting Helicopter or Glider Time
SkyWest Airlines recognizes the skills common to helicopter and glider flying. SkyWest will accept helo/glider time as part of an applicant's total time as long as they have a minimum of 250 PIC hours of fixed wing.

Domiciles

Arizona:  Phoenix, Tucson

California:  Fresno, Los Angeles, Palm Springs, San Diego, San Francisco

Colorado: Colorado Springs, Denver
Georgia: Atlanta

Idaho: Boise

Illinois: Chicago

Minnesota: Minneapolis/St. Paul

Michigan: Detroit

Oregon: Portland

Texas: Austin, Dallas, Houston

Utah: Salt Lake City

Washington: Seattle

Wisconsin: Milwaukee


Minimum Requirements
  • Assist the Pilot- in- Command (PIC) in conducting the flight safely and efficiently
  • Assist the PIC and/or passenger service personnel as needed to ensure a prompt departure
  • Assist or relieve the PIC in manipulation of the flight controls of an aircraft while underway, including taxiing, takeoff and landing of such aircraft

Physical and Other Requirements
  • Must have a First Class Medical
  • Must be willing to fly assigned schedule based on pilot bidding seniority; including days, nights, weekends, and holidays
  • To apply, please complete the on-line application (qualified applicants will be contacted)
Qualifications:

To be considered for a pilot position, you must: 

Be at least 21 years of age 
Hold a Commercial Pilot Certificate with Multi-Engine and Instrument Ratings
English Proficiency Endorsement (EPE) on Airman Certificate
Hold a current FAA First Class Medical Certificate
Be a U.S. citizen or able to show proof of right to work in the U.S. 
Hold FCC Radiotelephone Operator's Permit.
Have a current Passport --or other travel documents enabling the bearer to freely exit and re-enter the U.S. (multiple reentry status) and be legally eligible to work in the U.S. (possess proper working documents).
Must be available to work on any day, seven days a week, including nights, weekends and holidays.
Be within three months of the minimum hour requirements detailed below

ATP Written Requirement: 

SkyWest will provide the means to complete a SkyWest-approved CTP course for those who complete an application and successfully pass the pilot interview. 
 

Pilot applicants must meet the experience requirements of FAR 61.159 prior to employment.  

SkyWest Minimum Requirements When Counting Helicopter or Glider Time
SkyWest Airlines recognizes the skills common to helicopter and glider flying. SkyWest will accept helo/glider time as part of an applicant's total time as long as they have a minimum of 250 PIC hours of fixed wing.

Domiciles

Arizona:  Phoenix, Tucson

California:  Fresno, Los Angeles, Palm Springs, San Diego, San Francisco

Colorado: Colorado Springs, Denver
Georgia: Atlanta

Idaho: Boise

Illinois: Chicago

Minnesota: Minneapolis/St. Paul

Michigan: Detroit

Oregon: Portland

Texas: Austin, Dallas, Houston

Utah: Salt Lake City

Washington: Seattle

Wisconsin: Milwaukee

Education:UNAVAILABLEEmployment Type: FULL_TIME

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