ZipRecruiter

Log In

1

Freelance Second In Command Pilot Jobs in Chicago, IL

SkyWest Airlines

First Officer Pilot

Chicago, IL

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 ...

Blue Plate Catering

Chef de Cuisine

Chicago, IL · On-site

$68K - $93K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

Serve as the second-in-command to the Executive Chef, overseeing daily kitchen operations and ensuring smooth execution in their absence. * Lead, mentor, and develop the culinary leadership team ...

BLUE PLATE CATERING LTD

Chef de Cuisine

Chicago, IL

$68K - $93K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

Leadership & Team Development Serve as the second-in-command to the Executive Chef, overseeing daily kitchen operations and ensuring smooth execution in their absence. Lead, mentor, and develop the ...

Blue Plate Catering

Chef de Cuisine

Chicago, IL · On-site

$68K - $93K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

Leadership & Team Development • Serve as the second-in-command to the Executive Chef, overseeing daily kitchen operations and ensuring smooth execution in their absence. • Lead, mentor, and ...

Arrow Technologies

Sous Chef

Chicago, IL · On-site

$51K - $69K/yr

Ensuring that the kitchen operates in a timely way that meets our quality standards Job brief We are looking for a professional Sous Chef to be the second in command in our kitchen, following our ...

Arrow Technologies, Inc

Sous Chef

Chicago, IL

$51K - $69K/yr

Ensuring that the kitchen operates in a timely way that meets our quality standards Job brief We are looking for a professional Sous Chef to be the second in command in our kitchen, following our ...

Bozzuto

Assistant General Manager

Chicago, IL · On-site

You're a quick thinker and thrive in a fast-paced environment, yet your obsession for details positions you perfectly for this second in command role. As an Assistant General Manager (AGM), your ...

New

KFC

KFC Assistant Restaurant Manager

Streamwood, IL · On-site

As an Assistant Restaurant Manager, you are second in command of a $1 million+ business. Working with your Restaurant General Manager, you grow the business by making our customers' day. And when you ...

KFC

KFC Assistant Restaurant Manager

Chicago, IL · On-site

As an Assistant Restaurant Manager, you are second in command of a $1 million+ business. Working with your Restaurant General Manager, you grow the business by making our customers' day. And when you ...

KFC

KFC Assistant Restaurant Manager

Chicago, IL · On-site

As an Assistant Restaurant Manager, you are second in command of a $1 million+ business. Working with your Restaurant General Manager, you grow the business by making our customers' day. And when you ...

KFC

KFC Assistant Restaurant Manager

Chicago, IL · On-site

As an Assistant Restaurant Manager, you are second in command of a $1 million+ business. Working with your Restaurant General Manager, you grow the business by making our customers' day. And when you ...

KFC

KFC Assistant Restaurant Manager

Wauconda, IL · On-site

As an Assistant Restaurant Manager, you are second in command of a $1 million+ business. Working with your Restaurant General Manager, you grow the business by making our customers' day. And when you ...

previous pagenext page

Showing results 21-40

All JobsSecond In Command Pilot JobsFreelance Second In Command Pilot JobsFreelance Second In Command Pilot Jobs in Chicago, IL

Freelance Second In Command Pilot information

See Chicago, IL salary details

$9

$23

$71

How much do freelance second in command pilot jobs pay per hour?

As of Aug 16, 2026, the average hourly pay for freelance second in command pilot in Chicago, IL is $23.66, according to ZipRecruiter salary data. Most workers in this role earn between $19.33 and $19.33 per hour, depending on experience, location, and employer.

What is a freelance second in command pilot?

A Freelance Second In Command (SIC) Pilot is a licensed aviator who assists the Captain (or Pilot in Command) during flights, but is not permanently employed by a single airline or operator. Instead, they work on a contract or per-flight basis for various companies or individuals. Their responsibilities include supporting the Captain in flying the aircraft, monitoring instruments, managing communications, and ensuring flight safety. Freelance SIC pilots often work in business aviation, charter operations, or on-demand flight services, and their schedules can be highly flexible. This role requires proper certifications and adherence to aviation regulations.

What are the key skills and qualifications needed to thrive as a freelance second in command pilot?

To thrive as a Freelance Second In Command Pilot, you need a valid commercial pilot license with multi-engine and instrument ratings, strong aviation knowledge, and flight experience in the relevant aircraft type. Familiarity with flight management systems, navigation tools, and compliance with FAA regulations is essential, along with recurrent training and type ratings as required. Excellent situational awareness, teamwork, and communication skills help ensure smooth coordination with the captain and crew. These skills and qualifications are critical for maintaining safety, regulatory compliance, and effective flight operations in a dynamic aviation environment.

What are the most common challenges faced by a freelance second in command pilot, and how can they be addressed?

Freelance Second In Command Pilots often face challenges such as adapting quickly to different aircraft, flight crews, and company procedures, since each assignment may involve a new operator. Building rapport with captains and integrating into unfamiliar teams efficiently is essential for safe and effective operations. Staying current with various aircraft systems and maintaining required certifications can also be demanding, so ongoing self-study and recurrent training are crucial. Networking with operators and maintaining a reputation for professionalism can help secure consistent work and career advancement.

What is the difference between Freelance Second In Command Pilot vs Freelance First In Command Pilot?

AspectFreelance Second In Command PilotFreelance First In Command Pilot
CertificationsCommercial Pilot License (CPL), Second Class or Airline Transport Pilot License (ATPL)Commercial Pilot License (CPL), Airline Transport Pilot License (ATPL)
Work EnvironmentAssisting the captain, flying under supervision, in various aircraft typesLeading flights, making final decisions, overall flight responsibility
Employer & Industry UsageCharter companies, private operators, aerial toursAirlines, private charters, corporate flight services

In summary, the Freelance Second In Command Pilot assists the lead pilot and operates under supervision, while the Freelance First In Command Pilot holds the primary responsibility for flight safety and decision-making. Both roles require similar certifications but differ in authority and responsibilities during flights.

What are the most commonly searched types of Second In Command Pilot jobs in Chicago, IL?

The most popular types of Second In Command Pilot jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Freelance Second In Command Pilot jobs?

Cities near Chicago, IL with the most Freelance Second In Command Pilot job openings:

Freelance Second In Command Pilot jobs near you

First Officer Pilot

SkyWest Airlines

Chicago, IL

Full-time

Re-posted 8 days ago

SkyWest Airlines rating

7.1

Company rating: 7.1 out of 10

Based on 80 frontline employees who took The Breakroom Quiz

13th 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

What SkyWest Airlines employees say

Pay

Benefits

Hours and flexibility

Workplace

Get the full story on Breakroom

Apply