ZipRecruiter

Log In

1

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 Heating

Apprentice Plumber

Bridgeview, IL · On-site

$50K - $100K/yr

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

Four Seasons Heating

Apprentice Plumber

Hobart, IN · On-site

$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

next page

Showing results 1-20

People also search for

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 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.
Underwriting Specialist OR Executive Underwriter, Large Property

Underwriting Specialist OR Executive Underwriter, Large Property

Zurich Insurance Group

Chicago, IL • Hybrid

Other

Posted 15 days ago

Job description

Zurich is seeking an Underwriting Specialist OR Executive Underwriter, Large Property for our National Accounts Large Property Underwriting team in our Chicago office. While this position will be based out of a Zurich office, you will have the flexibility to work on a hybrid basis. You will partner with your manager to set a flexible work schedule that supports you, our customers, and our brokers and agents. This role will require you to be visible in the marketplace to meet with our agents and brokers and be in the office/market three days per week.

This role will be filled at either the Property Underwriting Specialist OR Executive Underwriter level. The hiring manager will determine the appropriate level based upon the selected applicant's experience and skill set relative to the qualifications listed for this position.

As a Property Underwriting Specialist OR Executive Underwriter, Large Property you will have a chance to use your marketing and analytical skills. Specifically, you will analyze and underwrite new and renewal business, under general direction, utilizing The Zurich Way of Underwriting Framework within delegated authority levels on assignments of higher technical complexity ensuring a high level of service to customers. This is a market facing position thus we are seeking someone with a strong sales execution mindset and knowledge of commercial property policies.
Some of the key accountabilities of this role include:

  • Administer and monitor underwriting rules and guidelines, rating manual rules, and insurance laws and regulations.
  • Develop, maintain & collaborate with Line of Business representatives and other business related needs, as appropriate.
  • Develop and maintain relationships with distributors (agents & brokers) in support of business retention and acquisition and works with customers and distributors (agents & brokers) to determine their insurance related needs and provide solutions.
  • Support the organization's sales culture by being a Help Point for agents, brokers and customers.
  • Proactively seek renewal and new account opportunities.
  • Complete detailed opportunity assessment with key distributors to identify growth opportunities.
  • Qualify accounts to meet with the organization's appetite, balanced with sound business opportunity.
  • Make broker/customer and on-sight calls with a planned and well-prepared purpose.

Basic Qualifications - Underwriting Specialist, Large Property:

  • High School Diploma or Equivalent and 3 or more years of experience in the Underwriting or Market Facing area.
    OR
  • High School Diploma or Equivalent and 6 or more years of experience in the Claims or Underwriting Support area
    OR
  • Zurich Certified Insurance Apprentice including an Associate Degree and 1 or more years of experience in the Underwriting or Market Facing area
    OR
  • Zurich Certified Insurance Apprentice including an Associate Degree and 4 or more years of experience in the Claims or
    Underwriting Support area
    AND
  • Knowledge of line/s of business and the legal and regulatory guidelines
  • Knowledge of time restraints for quotes on new and renewal business
  • Experience with Microsoft Office

OR

Basic Qualifications - Executive Underwriter, Large Property:

  • High School Diploma or Equivalent and 5 or more years of experience in commercial underwriting or brokerage or market facing area
    OR
  • High School Diploma or equivalent and 10 or more years of experience in the claims or underwriting support area
    OR
  • Zurich approved Apprenticeship program including an Associate Degree and 3 or more years of experience in the Underwriting or Market Facing area
    OR
  • Zurich approved Apprenticeship program including an Associate Degree and 8 or more years of experience in the Claims or Underwriting Support area
  • Knowledge of Microsoft Office
  • Experience working on time restraints for quotes on new and renewal business
  • Experience working in a team environment

Preferred Qualifications (Both levels):

  • Bachelors Degree 
  • Technical knowledge of commercial Property Underwriting
  • Established broker relationships (Retail, select brokers) in Midwestern Region
  • Sales execution mindset
  • Creative problem solving skills
  • Strong verbal and written communication skills

Your pay at Zurich is based on your role, location, skills, and experience. We follow local laws to ensure fair compensation. You may also be eligible for bonuses and merit increases. If your expectations are above the listed range, we still encourage you to apply-your unique background matters to us. The combined salary range for this position is $83,400,00 - $180,500.00. The proposed salary range for the Underwriting Specialist is $83,400,00 - $136,500.00, with short-term incentive bonus eligibility set at 10%. The proposed salary range for the  Executive Underwriter is $110,200,00 - $180,500.00, with short-term incentive bonus eligibility set at 15%.

We offer competitive pay and comprehensive benefits for employees and their families. [Learn more about Total Rewards here.]

 

Why Zurich?

At Zurich, we value your ideas and experience. We offer growth, inclusion, and a supportive environment-so you can help shape the future of insurance. Zurich North America is a leader in risk management, with over 150 years of expertise and coverage across 25+ industries, including 90% of the Fortune 500.

Join us for a brighter future-for yourself and our customers.

Zurich in North America does not discriminate based on race, ethnicity, color, religion, national origin, sex, gender expression, gender identity, genetic information, age, disability, protected veteran status, marital status, sexual orientation, pregnancy or other characteristics protected by applicable law. Equal Opportunity Employer disability/vets.

Zurich complies with 18 U.S. Code 1033.

 

Please note: Zurich does not accept unsolicited CVs from agencies. Preferred vendors should use our Recruiting Agency Portal.

Location(s): AM - Chicago
Remote Working: Hybrid
Schedule: Full Time
Employment Sponsorship Offered: No  
Linkedin Recruiter Tag: #LI-BN1 #LI-ASSOCIATE #LI-HYBRID 

Apply