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Entry Level Insurance Agent Training Program Jobs in Chicago, IL

Big I Illinois

Insurance Agent

IL · On-site +1

$60K - $150K/yr

We have systems, training, vendors, mentorship, best practices, and more to support you in that ... Compensation: $60,000.00 - $150,000.00 per year YOUR FUTURE as an Independent Insurance Agent ...

Fay Financial

Insurance Agent

Mokena, IL · Hybrid

$48K/yr

We are currently looking for an Insurance Agent to join our team. Reporting to the EVP, Genstone ... Pet Insurance * 401k Program with Employer Matching * 3 Weeks Paid Time Off (PTO) * Paid Holidays

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All JobsInsurance Agent Training Program JobsEntry Level Insurance Agent Training Program JobsEntry Level Insurance Agent Training Program Jobs in Chicago, IL

Entry Level Insurance Agent Training Program information

See Chicago, IL salary details

$25.8K

$67K

$125.2K

How much do entry level insurance agent training program jobs pay per year?

As of Jun 9, 2026, the average yearly pay for entry level insurance agent training program in Chicago, IL is $66,982.00, according to ZipRecruiter salary data. Most workers in this role earn between $45,800.00 and $79,300.00 per year, depending on experience, location, and employer.

What is the difference between Entry Level Insurance Agent Training Program vs Insurance Sales Associate?

AspectEntry Level Insurance Agent Training ProgramInsurance Sales Associate
Required CredentialsHigh school diploma or equivalent; licensing required post-trainingHigh school diploma or equivalent; licensing often required
Work EnvironmentClassroom training, mentorship, and fieldworkOffice or retail environment, direct customer interaction
Employer & Industry UsageInsurance companies, agencies, and brokeragesInsurance agencies, brokerages, and direct sales roles
Common Search & ComparisonTraining programs for new agentsEntry-level sales roles in insurance

The Entry Level Insurance Agent Training Program focuses on preparing individuals through structured training and licensing, often with a mentorship component. In contrast, an Insurance Sales Associate typically involves direct sales and customer service in an office or retail setting. Both roles require licensing and are common entry points into the insurance industry, but the training program emphasizes education and skill development before active sales duties.

What are the most commonly searched types of Insurance Agent Training Program jobs in Chicago, IL? The most popular types of Insurance Agent Training Program jobs in Chicago, IL are:
Entry Level Insurance Agent Training Program jobs near you
Infographic showing various Entry Level Insurance Agent Training Program job openings in Chicago, IL as of June 2026, with employment types broken down into 75% Full Time, and 25% Part Time. Highlights an 87% In-person, and 13% Remote job distribution, with an average salary of $66,982 per year, or $32.2 per hour.
Insurance Sales Agent

Insurance Sales Agent

HealthMarkets, Inc.

Aurora, IL

Contractor

Posted 7 days ago

Job description

HealthMarkets Overview

If youre looking for an exciting opportunity where you can change peoples lives and achieve financial success as an independent insurance agent, youve come to the right place. Becoming an independent insurance agent with HealthMarkets is an opportunity unlike any other. HealthMarkets offers agents the resources and support they need to grow their businesses and succeed in the industry, all while making a difference in peoples lives.

And who are we? HealthMarkets is a technology-enabled health insurance agency delivering high-touch, customized health and supplemental insurance solutions to individuals, families and small businesses. Millions of Americans depend on us to help explore their coverage options and were looking for independent insurance agents like you to help us continue that mission.

So, whether youre an experienced insurance agent looking for your next opportunity or are just starting out and looking for an opportunity to demonstrate your talents, HealthMarkets is the career move that can help change your life.

Job description

Never worked in the health insurance industry before? Its no problem. If youve got an entrepreneurial spirit and drive and are ready to start your own business, we want you. At HealthMarkets, independent agents are given the opportunity to achieve financial success on their own time and schedule. Need to coach your childs soccer game? Or show up to a family event? Youve got the time because you work for yourself.

Plus, the opportunities for growth are endless. We provide you with the support, training, and resources you need to succeed on your terms. Get started today and watch your career take off to new heights.

48640-HM-0523

Disclaimer: Licensed Insurance Agents with HealthMarkets Insurance Agency are self-employed acting as independent contractors and not as employees. HealthMarkets independent licensed insurance agents shall for all purposes be deemed to be independent contractors and shall have no authority to act or represent themselves as an employee or partner of HealthMarkets Insurance Agency. An Independent licensed insurance agent with HealthMarkets is a commission only opportunity. HealthMarkets Insurance Agency, Inc., is licensed as an insurance agency nationwide except in MA. Not all agents are licensed to sell all products. Service and product availability may vary by state. 51934-HM-0326

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