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Insurance Apprentice Jobs in Chicago, IL (NOW HIRING)

Crawford and Company

Insurance Apprentice

Schaumburg, IL · On-site

$16.75 - $21.75/hr

Insurance Apprentice! Learn. Earn. Grow. Kickstart your future with the Crawford Claims Apprentice Program -a dynamic, paid two-year opportunity built for ambitious individuals ready to grow fast.

Crawford and Company

Insurance Apprentice

Schaumburg, IL · On-site

$16.75 - $21.75/hr

Insurance Apprentice! Learn. Earn. Grow. Kickstart your future with the Crawford Claims Apprentice Program -a dynamic, paid two-year opportunity built for ambitious individuals ready to grow fast.

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Insurance Apprentice information

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$12

$22

$38

How much do insurance apprentice jobs pay per hour?

As of Jun 11, 2026, the average hourly pay for insurance apprentice in Chicago, IL is $22.69, according to ZipRecruiter salary data. Most workers in this role earn between $17.84 and $24.76 per hour, depending on experience, location, and employer.

What are Insurance Apprentices?

Insurance Apprentices are entry-level professionals who learn about the insurance industry while working under the guidance of experienced mentors. They typically participate in a structured program that combines on-the-job training with classroom learning, gaining knowledge about various insurance products, policies, regulations, and customer service. The apprenticeship helps individuals develop both technical and soft skills needed for a career in insurance, and often leads to a permanent position upon successful completion.

What are the key skills and qualifications needed to thrive as an Insurance Apprentice, and why are they important?

To thrive as an Insurance Apprentice, you should have a solid grasp of basic mathematics, attention to detail, and an eagerness to learn about insurance principles, often supported by a high school diploma or equivalent. Familiarity with office software, customer relationship management (CRM) systems, and sometimes basic insurance certification courses are valuable. Strong communication, problem-solving abilities, and a proactive attitude help apprentices build relationships and adapt quickly in the workplace. These skills are essential for accurately handling client information, supporting experienced staff, and developing a successful insurance career.

What types of projects or assignments can an Insurance Apprentice expect to handle during their training period?

As an Insurance Apprentice, you can expect to be involved in a variety of hands-on assignments such as processing policy applications, assisting with claims investigation, and supporting customer service inquiries. You'll often shadow experienced agents and underwriters to learn about risk assessment and policy quoting. Apprentices also participate in administrative tasks and may help prepare client presentations or reports, providing a broad overview of the insurance business. This practical exposure is designed to build your confidence and understanding of the industry's workflows before taking on more responsibility.

What is the difference between Insurance Apprentice vs Insurance Agent?

AspectInsurance ApprenticeInsurance Agent
Required CredentialsTypically no formal licensing initially; may need to obtain licenses laterMust be licensed in the state to sell insurance
Work EnvironmentTraining programs, office settings, or on-the-job learningClient-facing, sales-focused, often in offices or client locations
Employer & Industry UsageEntry-level role within insurance companies or agenciesLicensed professionals working independently or for agencies
Search & Comparison IntentLearning role, entry-level position, trainingSales, licensing, client interaction

The main difference is that an Insurance Apprentice is an entry-level trainee often in training, while an Insurance Agent is a licensed professional actively selling insurance products. Apprentices typically focus on learning and gaining experience, whereas agents handle client interactions and sales after obtaining necessary licenses.

What are the most commonly searched types of Insurance jobs in Chicago, IL? The most popular types of Insurance jobs in Chicago, IL are:
Insurance Apprentice jobs near you
Infographic showing various Insurance Apprentice job openings in Chicago, IL as of June 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $47,187 per year, or $22.7 per hour.
Insurance Apprentice

Insurance Apprentice

Crawford and Company

Schaumburg, IL • On-site

$16.75 - $21.75/hr

Full-time

Posted 23 days ago

Job description

Now Hiring: Insurance Apprentice!
Learn. Earn. Grow.

Kickstart your future with the Crawford Claims Apprentice Program-a dynamic, paid two-year opportunity built for ambitious individuals ready to grow fast. This isn't just a job-it's your launchpad into the insurance industry.

You'll gain hands-on experience through exciting work rotations in Crawford's Chicago offices while completing targeted coursework at Harper College-giving you the perfect blend of real-world learning and academic development.

Gain practical skills
Build industry knowledge
Develop tools for long-term success

Step into real challenges, build a strong professional foundation, and unlock your potential. If you're driven, curious, and ready to level up-this is your chance to learn, earn, and thrive-all at once!

Why Crawford?
Because a claim is more than a number - it's a person, a child, a friend. It's anyone who looks to Crawford on their worst days. And by helping to restore their lives, we are helping to restore our community - one claim at a time.
At Crawford, employees are empowered to grow, emboldened to act and inspired to innovate. Our industry-leading team pioneers new solutions for the industries and customers we serve. We're looking for the next generation of leaders to take this journey with us.
We hail from more than 70 countries and speak dozens of languages, reflecting the global fabric of the audience we serve. Though our reach is vast, we proudly operate as One Crawford: united in purpose, vision and values. Learn more at www.crawco.com.
When you accept a job with Crawford, you become a part of the One Crawford family.
Our total compensation plans provide each of our employees with far more than just a great salary
  • Pay and incentive plans that recognize performance excellence
  • Benefit programs that empower financial, physical, and mental wellness
  • Training programs that promote continuous learning and career progression while enhancing job performance
  • Sustainability programs that give back to the communities in which we live and work
  • A culture of respect, collaboration, entrepreneurial spirit and inclusion
Crawford & Company participates in E-Verify and is an Equal Opportunity Employer. M/F/D/V Crawford & Company is not accepting unsolicited assistance from search firms for this employment opportunity. All resumes submitted by search firms to any employee at Crawford via-email, the Internet or in any form and/or method without a valid written Statement of Work in place for this position from Crawford HR/Recruitment will be deemed the sole property of Crawford. No fee will be paid in the event the candidate is hired by Crawford as a result of the referral or through other means.
  • High School diploma or equivalent
  • One (1) or more years of work experience and/or voluntary community service is preferred.
  • One (1) or more years of work experience and/or voluntary community service is preferred.
  • Basic computer skills
  • Good oral and written communication skills
  • Attention to detail
  • A passion for helping our claimants by listening, investigating, having empathy, using emotional intelligence, and utilizing time management skills to assist them on their road to recovery
  • Must be capable of working in a fast paced environment and the ability to learn to be flexible, adaptable, and develop excellent multi-tasking and communication skills
  • At least 18 years of age
  • High School diploma or equivalent
  • US Citizen or Work Visa
  • Valid Driver's License
  • Enrolled and validated as college ready by Harper College Admissions
  • Executed Crawford Insurance Apprentice Offer Letter
  • Executed Harper College/Employer/Apprentice Agreement
  • Open to job opportunities at the conclusion of the program that may include relocation

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  • While working closely with a highly trained mentor, learn and demonstrate the aspects of insurance claims handling and independent/Third Party Administrator adjusting, including, but not limited to:
    • The basics of claims adjusting
    • Use of a claim system
    • Electronic document retention and claim file documentation
    • Claim investigation
    • Claim damage assessment - injury and property related items
    • Claim valuation assessment
    • Key Performance Indicators (KPI) Compliance
    • Diary management
    • Client relationship building
  • Maintain acceptable product quality through compliance with service standards
  • Upholds the Crawford Code of Conduct.

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