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Live In Ferry Pilot Jobs in Chicago, IL (NOW HIRING)

JLL

Senior Software Engineer

Chicago, IL · Remote

$126K - $166K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... in their workflows, learning their systems, and turning their expertise into agents that go live ... Translate integration and capability gaps you hit during pilots into clear, prioritized ...

Legal Aid Chicago

Supervisory Attorney - Housing

Chicago, IL · On-site

$95K - $105K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

HPG seeks to ensure that tenants live in decent, safe, and sanitary housing, free from ... HPG is also a partner in City of Chicago Right to Counsel Pilot. The Supervisory Attorney will ...

JLL

Senior Software Engineer

Chicago, IL · On-site

$126K - $166K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... in their workflows, learning their systems, and turning their expertise into agents that go live ... Translate integration and capability gaps you hit during pilots into clear, prioritized ...

Jones Lang LaSalle IP, Inc.

Senior Software Engineer

Chicago, IL · On-site

$126K - $166K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... in their workflows, learning their systems, and turning their expertise into agents that go live ... Translate integration and capability gaps you hit during pilots into clear, prioritized ...

JLL

Staff Software Engineer

Chicago, IL

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... in their workflows, learning their systems, and turning their expertise into agents that go live ... Translate integration and capability gaps you hit during pilots into clear, prioritized ...

Jones Lang LaSalle IP, Inc.

Senior Software Engineer

Chicago, IL · On-site

$126K - $166K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... in their workflows, learning their systems, and turning their expertise into agents that go live ... Translate integration and capability gaps you hit during pilots into clear, prioritized ...

Varsity Tutors

FAA Tutor

Des Plaines, IL · Remote

$18 - $40/hr

About the Job The Varsity Tutors Live Learning Platform has thousands of students looking for ... What We Look For In a FAA Tutor * Advanced Test Mastery: Deep knowledge of FAA knowledge ...

Legal Aid Chicago

Staff Attorney - Housing

Chicago, IL · On-site

$70K - $77K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

The Housing Practice Group (HPG) seeks to ensure that tenants live in decent, safe, and sanitary ... HPG is also a partner in City of Chicago Right to Counsel Pilot. Position : Legal Aid Chicago seeks ...

New

Varsity Tutors

FAA Tutor

Wheaton, IL · Remote

$18 - $40/hr

About the Job The Varsity Tutors Live Learning Platform has thousands of students looking for ... What We Look For In a FAA Tutor * Advanced Test Mastery: Deep knowledge of FAA knowledge ...

Varsity Tutors

FAA Tutor

Naperville, IL · Remote

$18 - $40/hr

About the Job The Varsity Tutors Live Learning Platform has thousands of students looking for ... What We Look For In a FAA Tutor * Advanced Test Mastery: Deep knowledge of FAA knowledge ...

Varsity Tutors

FAA Tutor

Highland Park, IL · Remote

$18 - $40/hr

About the Job The Varsity Tutors Live Learning Platform has thousands of students looking for ... What We Look For In a FAA Tutor * Advanced Test Mastery: Deep knowledge of FAA knowledge ...

Varsity Tutors

FAA Tutor

Lake Forest, IL · Remote

$18 - $40/hr

About the Job The Varsity Tutors Live Learning Platform has thousands of students looking for ... What We Look For In a FAA Tutor * Advanced Test Mastery: Deep knowledge of FAA knowledge ...

Varsity Tutors

FAA Tutor

Evanston, IL · Remote

$18 - $40/hr

About the Job The Varsity Tutors Live Learning Platform has thousands of students looking for ... What We Look For In a FAA Tutor * Advanced Test Mastery: Deep knowledge of FAA knowledge ...

Varsity Tutors

FAA Tutor

Schaumburg, IL · Remote

$18 - $40/hr

About the Job The Varsity Tutors Live Learning Platform has thousands of students looking for ... What We Look For In a FAA Tutor * Advanced Test Mastery: Deep knowledge of FAA knowledge ...

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Showing results 21-40

All JobsLive In Ferry Pilot JobsLive In Ferry Pilot Jobs in Chicago, IL

Live In Ferry Pilot information

See Chicago, IL salary details

$51K

$134.9K

$207.1K

How much do live in ferry pilot jobs pay per year?

As of Aug 12, 2026, the average yearly pay for live in ferry 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 live in ferry pilot?

A Live In Ferry Pilot is a professional pilot who specializes in transporting aircraft from one location to another, often over long distances or international borders. 'Live In' refers to the arrangement where the pilot temporarily resides near the client's location or with the client during the ferrying period, allowing greater flexibility and availability. This role is critical for aircraft delivery, relocation, or when owners need their planes moved but cannot fly them personally. Live In Ferry Pilots must be highly skilled, adaptable to various aircraft types, and knowledgeable in aviation regulations across different countries. They often work on a contract basis and may be responsible for planning the route, handling customs paperwork, and ensuring the safe transfer of the aircraft.

What is the difference between Live In Ferry Pilot vs Commercial Ferry Pilot?

AspectLive In Ferry PilotCommercial Ferry Pilot
CertificationsCommercial Pilot License, Ferry Pilot EndorsementCommercial Pilot License, Ferry Pilot Endorsement
Work EnvironmentResidential ferry routes, often remote locationsVarious routes, including urban and remote areas
Employer & IndustryFerry companies, transportation servicesFerry operators, transportation industry

Both Live In Ferry Pilots and Commercial Ferry Pilots require similar certifications and work in ferry transportation. The key difference is that Live In Ferry Pilots typically reside on-site and operate in remote or residential routes, while Commercial Ferry Pilots may work on a broader range of routes without living on-site. Understanding these distinctions helps candidates choose the role that best fits their lifestyle and career goals.

What are some common challenges faced by live in ferry pilots, and how can applicants prepare for them?

Live In Ferry Pilots often face challenges such as adapting to frequently changing schedules, navigating unfamiliar routes, and managing the physical demands of extended periods on the water. It’s important to be comfortable with flexible work hours and to have strong problem-solving skills for unexpected weather or mechanical issues. Applicants can prepare by gaining experience with a variety of vessel types, refining their navigation skills, and staying up-to-date with safety protocols. Teamwork and clear communication with crew members are also essential for success in this role.

How to get a job as a live in ferry pilot?

To become a live-in ferry pilot, candidates typically need a commercial pilot license with an instrument rating, experience in flying large aircraft or ferrying aircraft, and familiarity with navigation and safety protocols. Employers may also require specific certifications, a clean flying record, and the ability to work long hours in remote environments.

How much do live in ferry pilots make?

Live-in ferry pilots typically earn between $50,000 and $100,000 annually, depending on experience, the type of aircraft, and the employer. Compensation may include benefits such as housing, per diems, and overtime pay, with pilots often required to hold commercial pilot certificates and relevant flight hours.

What are the key skills and qualifications needed to thrive as a live in ferry pilot?

To thrive as a Live In Ferry Pilot, you need a commercial pilot license, strong navigation and flight planning skills, and thorough knowledge of aviation safety regulations. Familiarity with various aircraft types, proficiency in using avionics systems, and certifications like instrument and multi-engine ratings are typically required. Strong problem-solving, adaptability, and effective communication are essential soft skills for managing unexpected situations and coordinating with ground crews. These competencies ensure the safe, timely, and efficient delivery of aircraft, often across diverse and challenging environments.
What are the most commonly searched types of Ferry Pilot jobs in Chicago, IL? The most popular types of Ferry Pilot jobs in Chicago, IL are:
What job categories do people searching Live In Ferry Pilot jobs in Chicago, IL look for? The top searched job categories for Live In Ferry Pilot jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Live In Ferry Pilot jobs? Cities near Chicago, IL with the most Live In Ferry Pilot job openings:
Live In Ferry Pilot jobs near you
Infographic showing various Live In Ferry Pilot job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 71% Full Time, 25% Part Time, and 3% Contract. Highlights an 87% Physical, 2% Hybrid, and 11% Remote job distribution, with an average salary of $134,863 per year, or $64.8 per hour.

Technical Co-founder (CTO) - AI Legal Front Desk

FutureSight

Chicago, IL • On-site, Remote

Full-time

Re-posted 2 days ago

Job description

The Opportunity
Solo practitioners and small law firms still lose work the same way: missed calls, slow callbacks, and intake handled between hearings. Hiring is no answer - payroll, training, and turnover are exactly what these firms cannot absorb.
Problem and solution validation are complete. Multiple live pilots are entering production evaluation. The next phase is proving in-production reliability, delivery economics, and scalability. The teams that ship credible AI workers into trust-sensitive verticals in the next 18 months will define the category. We intend to be one of them.
The Venture
BloomLex is a managed AI staffing platform that delivers AI workers as fully-set-up hires - trained, monitored, and continuously improved by our team. Rather than another self-serve SaaS tool, BloomLex operates as a Role-as-a-Service business: lawyers evaluate us on outcomes - time saved, calls answered, consults booked - not configuration effort.
Our first hire, Ava, is an AI Front Desk that answers calls 24/7, captures structured intake, books consultations, and performs outbound callbacks, without creating new operational burden for the lawyer. The roadmap expands from the front desk into adjacent AI staff roles, all delivered through the same managed model.
The Partnership
The CEO co-founder is in place. The customer thesis is validated, design partners are engaged, and live pilots are running. What remains is to bring on the technical co-founder - a partner who will own product and engineering with the same conviction, urgency, and ownership stake.
This is a co-founder role, not a CTO hire. In return for that level of commitment, you receive founder-level equity, founder-level authority with co-decision rights on product, technology, hiring, fundraising, and strategy, and a genuine partnership with the CEO on every material decision.
What you'll own
As Co-Founder & CTO, you will write the first lines of production code, set the technical direction, and lead execution end-to-end.
  • Architecture & Reliability - Harden Ava's voice and workflow systems for in-production reliability. Establish core architecture, observability, and audit-trail standards
  • RaaS Delivery Layer - Build the internal infrastructure that lets the team configure, monitor, and optimize AI performance without scaling engineering headcount
  • Unit Economics - Own the trade-offs between AI quality and cost-per-call, and lock in unit economics within the $499/month pricing model
  • Customer & Market - Represent the company in front of lawyers, partners, and investors as the technical voice of the venture
  • Roadmap - Convert pilots into paying customers, expand the AI staff beyond the front desk, and begin a path toward custom and self-hosted models where legal and privacy requirements demand it
  • Team - Recruit and lead the founding engineering team, and establish the cultural foundation of the company
Co-Founder Profile
  • Shipped LLM-powered and voice systems into production environments where incorrect outputs carried real consequences
  • Full-stack confidence across applied LLMs, real-time voice and conversational AI, telephony, human-in-the-loop workflows, observability, and secure multi-tenant SaaS
  • Well-formed convictions about reliability engineering, edge-case management, and the trade-offs between AI quality and cost-per-call
  • Experience building managed and service-heavy platforms, with the discipline to scale delivery without scaling engineering headcount
  • Prepared to operate as a principal - including saying "this won't scale" or "this isn't ready" when the integrity of the product requires it
  • Strongly preferred: prior founder or early-stage technical leadership experience; background in legal tech, healthcare, or another trust-sensitive vertical; capability to self-host custom models to meet legal and privacy needs
How to Apply
Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate.
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.

Apply