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Sailing Jobs in Chicago, IL (NOW HIRING)

Echo Global Logistics

Pricing Analyst

Woodridge, IL · On-site

We handle refrigerated and LTL needs by leveraging no sailing schedules, our nationwide network of 32 strategically placed temperature-controlled facilities, our state-of-the-art tracking, and our ...

Echo Global Logistics

Pricing Analyst

Woodridge, IL · On-site

We handle refrigerated and LTL needs by leveraging no sailing schedules, our nationwide network of 32 strategically placed temperature-controlled facilities, our state-of-the-art tracking, and our ...

Roadtex Logistics

Pricing Analyst

Woodridge, IL · On-site

We handle refrigerated and LTL needs by leveraging no sailing schedules, our nationwide network of 32 strategically placed temperature-controlled facilities, our state-of-the-art tracking, and our ...

Roadtex Logistics

Pricing Analyst

Woodridge, IL · On-site

We handle refrigerated and LTL needs by leveraging no sailing schedules, our nationwide network of 32 strategically placed temperature-controlled facilities, our state-of-the-art tracking, and our ...

V3 Companies

Project Manager - Land Development

Woodridge, IL · On-site

$99K - $128K/yr

Steering client relationships towards a horizon of mutual success, ensuring smooth sailing in billing and satisfaction. * Guiding project design teams through the currents of creativity to deliver ...

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All JobsSailing JobsSailing Jobs in Chicago, IL

Sailing information

See Chicago, IL salary details

$7

$17

$24

How much do sailing jobs pay per hour?

As of Sep 8, 2026, the average hourly pay for sailing in Chicago, IL is $17.47, according to ZipRecruiter salary data. Most workers in this role earn between $16.35 and $19.33 per hour, depending on experience, location, and employer.

What are different types of sailing jobs?

Sailing jobs refer to careers or roles that involve working on or with sailboats and yachts. These can include positions such as sailing instructors, yacht crew members, charter captains, deckhands, and maintenance staff. People in sailing jobs may work on private yachts, with charter companies, at sailing schools, or in boat maintenance and repair. Responsibilities can range from navigating and maintaining the vessel to teaching sailing techniques or ensuring the safety of passengers. Sailing jobs often require practical seamanship skills, certifications, and a love for being on the water.

What are the qualifications to get a sailing job?

To get a job in the sailing industry, you need basic safety training and certification. Commercially registered yachts have legal requirements for the crew while other boat qualifications vary. Standards of Training, Certification, and Watchkeeping for Seafarers (STCW) training includes standard fire prevention and firefighting, first aid, and survival techniques. Maritime training is done through various organizations and employers look for applicants with hands-on experience. You also need a passport for any international travel. Other essential skills are knowing proper nautical terminology, physical stamina, and the ability to maintain calm under stress.

What are the key skills and qualifications needed to thrive as a sailor, and why are they important?

To thrive as a Sailor, you need strong seamanship, navigation, and safety knowledge, often supported by certifications such as a boating license or STCW (Standards of Training, Certification and Watchkeeping). Familiarity with navigation systems, communication devices, and vessel maintenance tools is essential. Teamwork, adaptability, and quick decision-making are vital soft skills for handling the dynamic environment at sea. These competencies ensure safety, efficient vessel operation, and effective response to changing maritime conditions.

What are some common challenges faced by professional sailors when working as part of a racing crew?

Professional sailors working on a racing crew often encounter challenges such as adapting to rapidly changing weather conditions, maintaining clear and effective communication with teammates, and executing complex maneuvers under pressure. The role requires strong teamwork, as each crew member relies on others for safety and performance. Additionally, long hours on the water and physically demanding tasks can be taxing, but these experiences foster resilience and camaraderie within the team.

What is the difference between Sailing vs Boating?

AspectSailing
Required CredentialsTypically requires sailing certifications or licenses, such as US Sailing certifications
Work EnvironmentOpen water, coastal or offshore locations, often involves navigation and weather assessment
Employer & Industry UsageMarinas, yacht clubs, charter companies, maritime tourism
Common Search & ComparisonOften compared due to similar recreational activities and skills involved

While both sailing and boating involve operating watercraft, sailing specifically refers to navigating boats powered primarily by sails, requiring knowledge of wind and navigation. Boating is a broader term that includes operating motorboats, kayaks, and other watercraft, often with different skill sets and certifications. Understanding these differences helps enthusiasts and professionals choose the right path for their interests or careers.

Can I sail with no experience?

Sailing jobs often require some level of experience, but entry-level positions or training programs may accept beginners. Basic skills such as understanding navigation, safety procedures, and operating equipment are typically learned on the job or through sailing courses before starting a professional role.

How to get a job sailing?

To get a sailing job, gain relevant experience through sailing courses and certifications such as STCW or RYA certifications. Look for opportunities on maritime job boards, network within the sailing community, and prepare a resume highlighting your sailing skills and safety training.
More about Sailing jobs

What are the most commonly searched types of Sailing jobs in Chicago, IL?

The most popular types of Sailing jobs in Chicago, IL are:

Sailing jobs near you
Infographic showing various Sailing job openings in Chicago, IL as of August 2026, with employment types broken down into 62% Full Time, 23% Part Time, and 15% Temporary. Highlights an 100% In-person job distribution, with an average salary of $36,329 per year, or $17.5 per hour.

Sailing Supervisor and Instructors

Lake Bluff Park District

Lake Bluff, IL • On-site

Full-time

Re-posted 18 days ago

Job description

The Lake Bluff Park District is an equal opportunity employer.

POSITION SUMMARY
The Sailing Supervisor and Instructor must be knowledgeable and enthusiastic about the sport of sailing and will expose students to the fundamentals of sailing as well as the importance of the natural environment in which we sail and the basic leadership skills inherent in the sport of sailing. The Sailing Supervisor will plan and prepare curriculum for sailing classes as well as oversee the sailing staff.  They will provide quality customer service to the families, park patrons, and Park District staff.
HOURS AND PAY
Various day and evening hours available Monday - Friday starting early to mid June and working through the beginning of August.  Must be available prior to the start of sailing camp for recruiting, hiring and planning.  




ESSENTIAL DUTIES
 Deliver a developmentally appropriate sailing program for registrants.
 Evaluate the success of the sailing program and the development of each registrant's sailing abilities and skills.
 Instructors will demonstrate a commitment to working as a team, and be supportive of the efforts of their fellow instructors.
 Be an appropriate role model for the students and sailing staff. Encourage the highest levels of sportsmanship and behavior. Generate enthusiasm and commitment to learning.
 Follow the course curriculum as designed. It is expected that Instructors will make full and constructive use of the time scheduled for classes, and show creativity and excitement with their classes to the best of their ability.
 Instructors are responsible for all landside and on-the-water aspects of the conduct of their classes. This includes assisting students with the preparation and launching of their sailboats, reviewing and insuring that rigging is done correctly, and that the boat(s) are in safe, working condition.
 Instructors are responsible for insuring that the safety boat(s) that they will be using for class has the necessary and required safety and teaching equipment, before going out on the water.
 At the end of the day, Instructors are responsible for making sure that all boats, both safety and sail, are properly secured and put away, and that any extraneous equipment or materials (including trash) has been removed.
 Instructors are responsible for reporting accidents/illness, both minor and serious to the appropriate chain of command, and for making the appropriate notes in the Injury Log.
 Instructors are responsible for reporting any problems with the condition of any boat (safety or sail) used in the program.
 Arrive and be ready to begin work at the scheduled time, dressed in appropriate attire.
 Performs other duties, as assigned.













SKILLS/QUALIFICATIONS
 At least 18 years old
 Ability to obtain First Aid and CPR certification within the first week of employment
Advanced Sailing Skills
 Must have a prior experience and a passion for sailing, the environment and working with kids.
 Ability to communicate and work with groups participating (age and skill levels) and provide necessary instruction to campers and staff.
 Must have a positive, enthusiastic and flexible attitude.
 Must possess strong problem solving skills and an ability to adapt to changing program needs depending on weather, number of students, number of boats, etc.








PHYSICAL DEMANDS
The work requires routine walking, standing, sitting and bending frequently; and climbing, balancing, stooping, and kneeling on an occasional basis.  The employee must be able to lift 20-50 pounds. The employee must have the ability to respond appropriately to situations requiring first aid. Must be able to assist registrants in an emergency (fire, evacuation, illness, or injury) and possess strength and endurance required to maintain constant supervision of registrants.



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