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

Hornblower

Captain Hourly- City Experiences

Chicago, IL · On-site

$28 - $38/hr

City Ferry, part of Hornblower Group's Ferry and Transportation Division, is the largest private ... Headquartered in Orlando, Florida, Hornblower Group's additional corporate offices reside in San ...

Harvey

Legal Engineer (In-House)

Chicago, IL · On-site

$220K - $320K/yr

We live by three values: Decisiveness, Simplicity, and Job's Not Finished. We act quickly on clear ... They lead collaborative pilot programs, guide prospects through what's possible with AI, and work ...

Harvey

Legal Engineer (In-House)

Chicago, IL · On-site

We live by three values: Decisiveness, Simplicity, and Job's Not Finished. We act quickly on clear ... They lead collaborative pilot programs, guide prospects through what's possible with AI, and work ...

Harvey

Legal Engineer (In-House)

Chicago, IL · On-site

We live by three values: Decisiveness, Simplicity, and Job's Not Finished. We act quickly on clear ... They lead collaborative pilot programs, guide prospects through what's possible with AI, and work ...

Harvey

Legal Engineer (Law Firm, Corporate)

Chicago, IL · On-site

$220K - $320K/yr

... pilot to the most complex, custom-built workflow. At Harvey, we segment the Legal Engineering ... under live in-practice pressure. In doing so, they don't just drive adoption; they shape Harvey ...

Chubb

Talent Development Business Partner

Chicago, IL · On-site

$85K - $100K/yr

Leadership coaching (Hogan, Korn Ferry, etc.) or similar. * Experience with self-assessments (not ... and live virtual instructor-led experiences. * Project and vendor management. * Working in B2B, ...

Chubb

Talent Development Business Partner

Chicago, IL · On-site

$85K - $100K/yr

Leadership coaching (Hogan, Korn Ferry, etc.) or similar. * Experience with self-assessments (not ... and live virtual instructor-led experiences. * Project and vendor management. * Working in B2B, ...

W S Darley & Co

Uncrewed Systems Specialist

Itasca, IL · On-site

$55K - $65K/yr

In addition to providing prompt technical support and ensuring smooth system performance, this role also supports live demonstrations as a drone pilot, showcasing system capabilities to customers and ...

W S DARLEY & CO

Uncrewed Systems Specialist

Itasca, IL · On-site

$55K - $65K/yr

In addition to providing prompt technical support and ensuring smooth system performance, this role also supports live demonstrations as a drone pilot, showcasing system capabilities to customers and ...

W S DARLEY & CO

Uncrewed Systems Specialist

Itasca, IL · On-site

In addition to providing prompt technical support and ensuring smooth system performance, this role also supports live demonstrations as a drone pilot, showcasing system capabilities to customers and ...

W S DARLEY & CO

Uncrewed Systems Specialist

Itasca, IL · On-site

$55K - $65K/yr

In addition to providing prompt technical support and ensuring smooth system performance, this role also supports live demonstrations as a drone pilot, showcasing system capabilities to customers and ...

Humanity One

GTM & Partnerships Lead

Mundelein, IL · On-site

$2.0K - $3.0K/wk

Helping convert pilots into paying customers and longer-term relationships * Identifying larger ... Interested in AI, consumer technology and startups * Comfortable operating in a fast-moving early ...

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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 Sep 1, 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 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 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.

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 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 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, 69% Full Time, 27% Part Time, and 3% Contract. Highlights an 86% Physical, 2% Hybrid, and 12% Remote job distribution, with an average salary of $134,863 per year, or $64.8 per hour.

Captain Annual - Marine Operations - City Cruises Chicago

Hornblower

Chicago, IL • On-site

$60K - $70K/yr

Full-time

Re-posted 8 days ago

Hornblower rating

6.6

Company rating: 6.6 out of 10

Based on 18 frontline employees who took The Breakroom Quiz

6th of 9 rated cruise lines

Job description

Hornblower Group is a global leader in experience and transportation. Spanning a 100-year history, Hornblower Group's portfolio of international offerings includes water- and land-based experiences and ferry and transportation services. City Experiences, Hornblower Group's premier experience division, offers dining and sightseeing cruises and walking and food tours through the City Cruises, Walks, and Devour brands. City Ferry, part of Hornblower Group's Ferry and Transportation Division, is the largest private operator of high-speed passenger and vehicle ferries in the United States, carrying more than 10 million passengers annually and operating services including NYC Ferry, Puerto Rico Ferry, and other regional ferry systemsHornblower Group's subsidiaries include Hornblower Marine, which provides vessel outhaul and maintenance services at Bridgeport Boatworks in Bridgeport, Connecticut, and Seaward Services, Inc., a full-service shipping, waterfront logistics and management company that specializes in the operation and maintenance of government and commercial vessels. Additionally, Anchor Operating System, LLC, a Hornblower Group subsidiary and independent entity, provides reservation, ticketing and website integration services for clients in the transportation, tourism and entertainment industries. Today, Hornblower Group's global portfolio covers over 10 countries, over 50 U.S. cities and serves more than 20 million guests annually. Headquartered in Orlando, Florida, Hornblower Group's additional corporate offices reside in San Francisco, California; Boston, Massachusetts; Chicago, Illinois; London, United Kingdom; New York, New York; Dublin, Ireland; and across Ontario, Canada. For more information, visit hornblowercorp.com.
Position Summary:
The successful Captain will greet all guests and ensure each guest is attended to in an appropriate manner ensuring consistently high levels of safety, quality, service, and guest satisfaction while maintaining a high level of profitability.
Duties and Responsibilities:
Cruise Execution
  • Rotate as cruise captain on cruises and ensure adherence to procedures detailed in the Product Management Guide. This includes thorough pre-cruise preparation, adherence to cruise scripts, supervision of crew, proper piloting of vessel, adherence to all Coast Guard rules and regulations, and guest satisfaction
  • Gather pertinent cruise event details from the other departments to ensure special guest requests are fulfilled thereby ensuring complete guest satisfaction
  • Conduct pre-cruise meetings and communicate to crew all necessary information regarding the cruise (special needs, boarding procedures, etc.)
  • Ensure that staff and guests adhere to all safety standards and procedures
  • Participate in the execution of the Safety Program, including emergency drills
  • Participate in the proper maintenance of all ship's systems and boarding facilities including but not limited to gangways, diesel, hydraulic, pneumatic, electrical, water (potable, raw, black, and gray), fire suppression, communications, and navigation
  • Ensure adherence to Coast Guard rules and regulations, and other federal and local rules and regulations
  • Ensure strict compliance to Emergency Response Plan
  • Execute other projects as assigned by management

Operations Team Management
  • Recruit non-exempt operations staff (crew) when necessary to fill vacant positions
  • Deliver training to new crew
  • Schedule crew according to staffing matrix
  • Adhere to Company's performance management guidelines for all discipline and termination situations
  • Recommend to Marine Management the promotion of crew to full-time annual positions
  • Develop positive working relationships with city department heads and peers
  • Develop strong teamwork within the staff

Guest Service
  • Resolve guest problems using strong guest service skills and exercising effective communication skills in keeping with company objectives and guest retention
  • Oversee the implementation and execution of safety programs in accordance with Coast Guard regulations and established Company policies
  • Resolve guest problems using strong guest service skills and exercising effective communication skills in keeping with company objectives and guest retention
  • Oversee the implementation and execution of safety programs in accordance with Coast Guard regulations and established Company policies

Physical Requirements
  • Ability to work onboard a moving vessel in varying weather and sea conditions, including maintaining balance and stability while underway.
  • Ability to stand and walk for extended periods, frequently throughout a shift.
  • Ability to navigate stairs, ladders, narrow passageways, and confined spaces commonly found onboard vessels.
  • Ability to lift, carry, push, and pull supplies, equipment, and inventory weighing up to 40 pounds independently.
  • Ability to bend, stoop, kneel, crouch, reach overhead, and perform repetitive motions as required in food service and hospitality operations.
  • Ability to respond quickly and effectively during normal operations, guest service situations, and emergency procedures.
  • Ability to safely work in a fast-paced environment with exposure to moving equipment, wet surfaces, temperature variations, and moderate noise levels.
  • Ability to visually inspect service areas, food presentation, cleanliness standards, and safety conditions.
  • Ability to communicate effectively with guests, crew members, and management in person and via radio or other communication devices.
  • Successfully complete vessel-specific safety and emergency training.
  • Ability to work flexible schedules, including evenings, weekends, holidays, and extended shifts as operational needs require.

Work Environment
  • Work is performed primarily onboard a Coast Guard-inspected passenger vessel, with duties split between dining, service, storage, galley-adjacent, and administrative areas.
  • Position requires regular movement throughout multiple decks and may involve occasional exposure to outdoor marine environments, including heat, humidity, rain, wind, and sunlight.
  • Must be able to safely perform duties while the vessel is docked or underway.

Other
• Additional job duties as assigned
Requirements & Qualifications:
  • High school diploma or equivalent required
  • Must currently possess 100-ton license with a satisfactory record
  • Minimum of five (5) years of marine experience-preferably to include two (2) years as a captain with an outstanding record
  • Detailed working knowledge of all ship's systems and their proper maintenance: gangways, diesel, hydraulic, pneumatic, electrical, water (potable, raw, black, and gray), fire suppression, communications, and navigation
  • Must be able to operate vessel in accordance with all Coast Guard rules and procedures
  • Vessel handling and navigation knowledge required
  • Able to communicate effectively in oral and written form
  • Able to effectively deal with internal and external guests some of whom will require high levels of patience tact and diplomacy
  • Ability to establish and maintain effective working relationships
  • Ability to analyze and solve problems
  • Demonstrated ability to manage multiple priorities/tasks
  • Proficient knowledge of Microsoft Office applications (especially Word & Excel)

The RESPECT Service System embodies our mission, vision, values and operating principles. By creating a company culture that puts RESPECT at its core, we believe it will drive us to achieve our goal of becoming a Global Experiences and Transportation Leader.
EEO / Disabled / Protected Veteran Employer. Hornblower is proud to be an Equal Employment Opportunity employer. We offer equal employment opportunities to all qualified individuals and prohibit discrimination and/or harassment of any type, including but not limited to discrimination and or harassment based upon race, religion, religious creed, color, national origin, ancestry, citizenship, sex, sexual orientation, gender, gender identity, gender expression, age, pregnancy or relation medical conditions, childbirth, breastfeeding, parental status, veteran and/or military status, disability (physical or mental), medical condition, genetic information or characteristics, political affiliation, domestic violence survivor status, marital status, or other characteristics prohibited by federal, state, or local law. Additionally, as a federal, state, and local contractor, Hornblower complies with government regulations, including affirmative action responsibilities for qualified individuals, where and as they apply. The company also participates in the E-Verify program in certain locations.

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