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Caribbean Airlines Pilot Jobs (NOW HIRING)

Tradewind

Northeast Regional Chief Pilot

West Harrison, NY · On-site

$155K - $200K/yr

... Caribbean. For more details visit www.flytradewind.com Requirements: About the Candidate / Role ... Discounted standby travel benefits on numerous major and regional US and international airlines * A ...

Tradewind

Pilot - PC-12 First Officer

West Harrison, NY · On-site

$450/day

... the Caribbean. For more details, visit www.flytradewind.com ESSENTIAL FUNCTIONS: * Tradewind ... airlines (after 6 months) * Discounts on hotels, rental cars, wireless, shipping, and more Position ...

Frontier Airlines

Analyst - Aviation Safety

Denver, CO · On-site

$58K - $77K/yr

S., Caribbean, Mexico and Latin America. Frontier's highly fuel-efficient, all-Airbus fleet is ... Pilot Office. 20% * Assist the ASAP Manager in managing the ASAP (Airline Safety, processing ...

Frontier Airlines

Analyst - Aviation Safety

Denver, CO

$58K - $77K/hr

S., Caribbean, Mexico and Latin America. Frontier's highly fuel-efficient, all-Airbus fleet is ... Pilot Office. 20% * Assist the ASAP Manager in managing the ASAP (Airline Safety, processing ...

NetJets & EJM

Pilot in Command Hawker 4000

Englewood, CO · On-site

$200K - $220K/yr

Simons GA, Teterboro, and occasional flights to the Caribbean. This is your chance to join a Part ... Certifications and Licenses FAA Airline Transport Pilot (ATP) First Class Medical Certificate Years ...

Mesa Airlines

Dispatch Apprentice

Mesa, AZ · On-site

$22/hr

Participants must agree to a commitment of working as a Mesa Airline Aircraft Dispatcher for at ... S., Canada, and Caribbean. An aircraft dispatcher is a critical part of our team for each takeoff ...

Jet OUT

CJ4 Captain - OPF

Opa Locka, FL · On-site

No airline travel to where your trip begins Benefits * 401(k) with company matching * Health ... ATP Pilot Certificate AMEL * Current 1st Class Medical Certificate * 3,500 TT * 1,500 Turbine PIC

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Caribbean Airlines Pilot information

See salary details

$49.5K

$130.9K

$201K

How much do caribbean airlines pilot jobs pay per year?

As of Sep 1, 2026, the average yearly pay for caribbean airlines pilot in the United States is $130,916.00, according to ZipRecruiter salary data. Most workers in this role earn between $100,000.00 and $155,000.00 per year, depending on experience, location, and employer.

What is a Caribbean Airlines pilot?

A Caribbean Airlines Pilot is responsible for operating the airline’s aircraft safely and efficiently, ensuring passengers and cargo are transported according to schedule. Pilots must adhere to aviation regulations, follow flight plans, and communicate with air traffic control. They also conduct pre-flight and post-flight inspections, monitor weather conditions, and handle in-flight challenges. This role requires extensive training, a commercial pilot license, and experience in aviation.

What does a typical work schedule look like for a Caribbean Airlines pilot?

Caribbean Airlines Pilots typically work on a roster-based schedule that includes varying shifts, overnight layovers, and international routes throughout the Caribbean and broader regions. Flight schedules can differ each month, with a combination of early mornings, evenings, weekends, and holidays depending on the airline's operational needs. Pilots are part of a coordinated team, working closely with co-pilots, cabin crew, and ground staff to ensure seamless operations. While the role can be demanding, it offers exciting travel opportunities and the potential for career progression to senior captain or training roles within the airline.

What are the key skills and qualifications needed to thrive in the Caribbean Airlines pilot position, and why are they important?

To thrive as a Caribbean Airlines Pilot, you need an Airline Transport Pilot License (ATPL), excellent aeronautical knowledge, and strong decision-making abilities. Familiarity with advanced flight management systems, aviation weather tools, and company-specific safety protocols is essential. Outstanding communication skills, situational awareness, and teamwork are important soft skills for this role. These skills and qualities are crucial for ensuring safe, efficient, and smooth flight operations while delivering top-tier customer service.

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What are the most commonly searched types of Caribbean Airlines Pilot jobs?

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Caribbean Airlines Pilot jobs near you
Infographic showing various Caribbean Airlines Pilot job openings in the United States as of August 2026, with employment types broken down into 93% Full Time, 6% Part Time, and 1% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $130,916 per year, or $62.9 per hour.

Simulator NSLI Pilot Instructor - Contractor

Sun Country Airlines

Minneapolis, MN • On-site

$700/wk

Full-time

Posted 11 days ago

Sun Country Airlines rating

6.2

Company rating: 6.2 out of 10

Based on 15 frontline employees who took The Breakroom Quiz

18th of 26 rated airlines

Job description

About Sun Country Airlines
We're not your average airline. We're agile, resilient, and full of unique opportunity. Here, you can grow as part of an ambitious team that safely and collectively supports each other, our travelers, and our community. Together, we're making travel more attainable.
With more than 40 years of Minnesota roots, we're a unique hybrid low-cost carrier offering diverse services including scheduled flights to destinations across the U.S., Canada, Central America, and the Caribbean, as well as charter and cargo operations around the world. At Sun Country, you'll be part of a growing airline, and an enthusiastic team focused on connecting our community with their favorite people and places.
Pilot Instructor - NSLI Overview:Sun Country Airlines is hiring a Pilot Instructor - NSLI to instruct pilots in-flight procedures and techniques and for prepare them for validations and evaluations. The Non-Sonority List Instructor (NSLI) Contractor conducts task and line-oriented training in Full Flight Simulators and Flight Training Devices for Sun Country Airlines line pilots.
Essential Roles and Responsibilities:
Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
  • Provide instruction and certifies completion of modules within the flight training segment of the Sun Country Qualification and Continuing Qualification curricula.
  • Develop and prepares module outlines, study materials, and instructional techniques as dictated by curriculum and pilot needs.
  • Understand the role and responsibilities of being an airline pilot including but not limited to: Pilot in Command and Second in Command duties, roles & responsibilities; Expectations for professionalism, leadership, decision making; Crew Resource and Threat and Error Management; Sun Country company policies and available resources
  • Regularly solicit attendees for honest feedback on course critiques
  • Present an organized briefing and lead substantive, interactive discussions
  • Closely adhere to approved curricula and allotted time slots for each instructional module;
  • Manage classroom and training resources; Set-up and breakdown of presentation materials (power point, manuals, white-boards, handouts, etc.)
  • Continually demonstrate ability to train and evaluate pilot performance in all phases of flight, including during normal and non-normal situations.
  • Embrace diverse people, thinking and styles
  • Make safety and security, of self and others, the priority
  • Observe pilots' actions and reactions during the training events to ensure integration of classroom and pre-briefing instruction
  • Provide a thorough de-brief to the students on their development at the completion of each of the modules.

Required Qualifications:
  • Applicant should be familiar with technology required for the job including, but not limited to:
    • Use of Apple iPad tablet to access instructor syllabus and briefing materials, navigational charts, operating manuals, periodic bulletins, turbulence charts, etc.
    • Establishing internet or cell data connections to access company information and schedules.
    • Use of Power Point, email, and email folders
  • The NSLI will be subject to initial, periodic, and random performance reviews both as a pilot and as an instructor during Initial and Continuing Qualification training
  • This is a safety sensitive position
  • Must have a minimum of 3,000 TT and 1,000 as Pilot in Command
  • Must have served as a Captain at a 14 CFR Part 121 Certified Air Carrier

Preferred Qualifications:
  • B737 type rating and line pilot experience
  • Recent experience as a Simulator Instructor, Simulator Check Airman, or Aircrew Program Designee experience at a 14 CFR Part 121 Certified Air Carrier within the last 24 months

Compensation:
This is a 1099 Contract position that pays $700 per event.
Work Location:
Minneapolis, MN (onsite)
Supervisory Responsibility:
None
Work Environment:
This job operates in a professional office environment. This role routinely uses standard office equipment such as computers, phones, photocopiers, filing cabinets.
Physical Demands:
The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. While performing the duties of this job, the employee is regularly required to talk or hear. The employee frequently is required to stand; walk; use hands or finger, handle or feel; and reach with hands and arms. The employee is occasionally required to sit; climb or balance, and stoop, kneel, crouch or crawl. The employee must frequently lift and/or move up to 10 pounds and occasionally lift and/or move up to 25 pounds. Specific vision abilities required by this job include close vision, distance vision, color vision, peripheral vision, depth perception and ability to adjust focus.
Other Duties:
The above statements are intended to provide a summary of key responsibilities and the anticipated work environment of an accountant. They are not intended to be an all-inclusive listing of job duties. Position expectations may change as the needs, or the requirements of the organization evolve.
AAP/EEO Statement:
It is the policy of Sun Country Airlines to provide equal employment opportunity (EEO) to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state or local law.
Sun Country Airlines respects and values every employee's contribution to our business. We believe that an important part of our strength comes from our people and their array of perspectives.
#LI-GK1
Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.

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