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Insurance Apprentice Jobs in Chicago, IL (NOW HIRING)

FOUR SEASONS MASTER

Apprentice Plumber

Elgin, IL

$100K/yr

Apprentice Plumber (Sponsored Apprenticeship Opportunities with Tuition & Schooling Support) Four ... Medical Insurance (employer subsidized) * Accident Insurance * Critical Illness Insurance

FOUR SEASONS MASTER

Apprentice Plumber

Hobart, IN

$100K/yr

Apprentice Plumber (Sponsored Apprenticeship Opportunities with Tuition & Schooling Support) Four ... Medical Insurance (employer subsidized) * Accident Insurance * Critical Illness Insurance

Dynomax Inc.

CNC Machinist Apprentice

Wheeling, IL · On-site

$18/hr

Registered Apprentice-CNC Machining Dynomax, Inc is a family owned company that designs ... Company-paid life insurance * 401(k) Plan with a generous Company match * Paid holidays, vacation ...

Dynomax Inc.

CNC Machinist Apprentice

Arlington Heights, IL · On-site

$18 - $23/hr

Registered Apprentice-CNC Machining Dynomax, Inc is a family owned company that designs ... Company-paid life insurance * 401(k) Plan with a generous Company match * Paid holidays, vacation ...

Dynomax Inc.

CNC Machinist Apprentice

Arlington Heights, IL · On-site

$18 - $23/hr

Registered Apprentice-CNC Machining Dynomax, Inc is a family owned company that designs ... Company-paid life insurance * 401(k) Plan with a generous Company match * Paid holidays, vacation ...

Dynomax Inc.

CNC Machinist Apprentice

Wheeling, IL · On-site

$18/hr

Registered Apprentice-CNC Machining Dynomax, Inc is a family owned company that designs ... Company-paid life insurance * 401(k) Plan with a generous Company match * Paid holidays, vacation ...

Dynomax Inc.

CNC Machinist Apprentice

Wheeling, IL · On-site

$18.50 - $23.50/hr

Registered Apprentice-CNC Machining Dynomax, Inc is a family owned company that designs ... Company-paid life insurance * 401(k) Plan with a generous Company match * Paid holidays, vacation ...

Dynomax Inc.

CNC Machinist Apprentice

Wheeling, IL · On-site

$18/hr

Registered Apprentice-CNC Machining Dynomax, Inc is a family owned company that designs ... Company-paid life insurance * 401(k) Plan with a generous Company match * Paid holidays, vacation ...

Dynomax Inc.

CNC Machinist Apprentice (Wheeling)

Wheeling, IL · On-site

$18.50 - $23.50/hr

Registered Apprentice-CNC Machining Dynomax, Inc is a family owned company that designs ... Company-paid life insurance * 401(k) Plan with a generous Company match * Paid holidays, vacation ...

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All JobsInsurance Apprentice JobsInsurance Apprentice Jobs in Chicago, IL

Insurance Apprentice information

See Chicago, IL salary details

$12

$22

$38

How much do insurance apprentice jobs pay per hour?

As of Sep 2, 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 is an insurance apprentice?

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 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 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 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.

How to get a job in insurance apprentice with no experience?

To become an insurance apprentice with no experience, focus on developing basic knowledge of insurance principles, customer service skills, and attention to detail. Many programs accept candidates with a high school diploma and provide on-the-job training, so applying to entry-level positions or apprenticeships through insurance companies or agencies is a good start.

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.

Apprentice Plumber

FOUR SEASONS MASTER

Elgin, IL

$100K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 26 days ago

Job description

Apprentice Plumber

(Sponsored Apprenticeship Opportunities with Tuition & Schooling Support)

Four Seasons Heating, Air Conditioning, Plumbing & Electrical

Now Hiring in Elgin, IL

Four Seasons Heating, Air Conditioning, Plumbing & Electric is a fast-growing, people-first company built on trust, integrity, and craftsmanship. We’re more than a service provider — we develop professionals and build careers.

We are currently seeking motivated Apprentice Plumbers who have foundational field experience and want a structured path to licensing with tuition and schooling support. If you’ve already started your plumbing journey and are ready to accelerate your career, this is your opportunity.

What You’ll Do

As an Apprentice Plumber at Four Seasons, you will:

  • Work alongside licensed plumbers on residential service calls
  • Learn diagnostics, repair, and installation techniques
  • Assist with fixture installs, piping, and system repairs
  • Develop professionalism and customer communication
  • Participate in sponsored classroom learning and certification programs
  • Maintain jobsite organization and company vehicle care
  • Follow safety standards and licensing requirements

Pay & Benefits

Compensation

  • Earnings up to $100,000+ annually based on apprenticeship level, skills, certifications, and performance
  • Overtime opportunities after 40 hours
  • Bi-weekly paychecks
  • Great earning potential - commission and bonus opportunities available in addition to regular pay

Schedule

Typically Monday – Friday, with rotating weekend coverage and rotating on-call responsibilities designed around work-life balance and shared responsibility across the team.

Benefits

  • Medical Insurance (employer subsidized)
  • Accident Insurance
  • Critical Illness Insurance
  • Hospital Indemnity Insurance
  • Dental Plans (free to employees)
  • Vision Plans (free to employees)
  • Short Term Disability (free to employees)
  • Long Term Disability
  • Basic Life Insurance (free to employees)
  • Holiday Pay
  • Paid Time Off
  • 401k with Matching
  • Credit Union
  • Cellular Discounts
  • Tuition Reimbursement

What We Offer

  • Tuition Assistance and Schooling Support
  • Two weeks of paid time off within first year of employment, with ability to earn more
  • Company-provided work vehicle as role progresses

Culture You’ll Love

We invest in people, not just positions. You’ll train under experienced professionals who care about your growth and well-being.

What You Bring

  • Minimum 1 year of plumbing field experience (sponsored or unsponsored apprenticeship)
  • Strong interest in professional growth in the plumbing trade
  • Valid driver’s license and reliable transportation
  • Ability to lift 50+ lbs and perform physically demanding tasks
  • Ability to work in confined spaces and challenging environments
  • Willingness to complete background check and onboarding requirements

Equal Opportunity Employer

Four Seasons is proud to be an Equal Opportunity Employer and maintains a diverse and inclusive workplace.

Reasonable Accommodation:

Four Seasons is an affirmative action and equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, disability, age, sexual orientation, gender identity, national origin, veteran status, or genetic information. Four Seasons is committed to providing access, equal opportunity and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. To request reasonable accommodation, contact Human Resources at 773-284-6161 Ext 5010.

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