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Insurance Agent Jobs in Chicago, IL (NOW HIRING)

HealthMarkets, Inc.

Insurance Sales Agent

Elgin, IL

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 ...

HealthMarkets, Inc.

Insurance Sales Agent

Joliet, IL

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 ...

HealthMarkets, Inc.

Insurance Sales Agent

Waukegan, IL · On-site

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 ...

Big I Illinois

Insurance Agent

IL · On-site +1

$60K - $150K/yr

... insurance and financial industry that want to be fiercely independent, but not alone. We have built Red Oak with a focus on being agent-centric by combining the best of the independent model and the ...

AO Summit Group

Licensed Insurance Agent

Chicago, IL · Remote

CA$750 - CA$9.0K/wk

  • Medical

  • Dental

  • Vision

  • Life

The Licensed Insurance Agent plays a vital role in providing personalized insurance solutions to individual clients. This position focuses on policy sales and delivering excellent customer service ...

AO Summit Group

Licensed Insurance Agent

Chicago, IL · Remote

CA$750 - CA$9.0K/wk

  • Medical

  • Dental

  • Vision

  • Life

The Licensed Insurance Agent plays a vital role in providing personalized insurance solutions to individual clients. This position focuses on policy sales and delivering excellent customer service ...

AAA The Auto Club Group

Insurance Agent

Chicago, IL · On-site

AAA The Auto Club Group is seeking a Field Life Agent in the Chicago area to solicit and sell Life ... The role requires strong knowledge of life insurance products, excellent communication, and the ...

AAA The Auto Club Group

Insurance Agent

Chicago, IL · On-site

AAA The Auto Club Group is seeking a Field Life Agent in the Chicago area to solicit and sell Life ... The role requires strong knowledge of life insurance products, excellent communication, and the ...

StaffMyAgency LLC

Insurance Agent

Mundelein, IL · On-site

$40K - $70K/yr

  • Dental

  • Life

  • PTO

This program offers a unique opportunity to learn the insurance business from the inside out while working directly with a successful mentor agent. You'll gain hands-on experience, extensive training ...

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Showing results 21-40

All JobsInsurance Agent JobsInsurance Agent Jobs in Chicago, IL

Insurance Agent information

See Chicago, IL salary details

$25.8K

$67K

$125.2K

How much do insurance agent jobs pay per year?

As of Aug 17, 2026, the average yearly pay for insurance agent 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 are the key skills and qualifications needed to thrive as an insurance agent, and why are they important?

To thrive as an Insurance Agent, you need a solid understanding of insurance products, sales techniques, and relevant regulations, often supported by a state insurance license. Familiarity with customer relationship management (CRM) software and quoting systems is typically required. Strong interpersonal skills, active listening, and persuasive communication help agents build trust and effectively address client needs. These competencies are vital for meeting sales targets, ensuring compliance, and maintaining long-term client relationships.

What are some common challenges insurance agents face when building their client base, and how can they overcome them?

Insurance Agents often encounter challenges such as establishing trust with new clients, differentiating themselves in a competitive market, and managing client rejections. To overcome these obstacles, agents typically focus on building strong relationships through personalized service, maintaining up-to-date product knowledge, and leveraging networking opportunities. Successful agents also use digital marketing tools and referrals to expand their reach and consistently follow up with prospects to nurture long-term relationships.

What is the difference between Insurance Agent vs Insurance Broker?

AspectInsurance AgentInsurance Broker
CredentialsLicensed to sell policies for specific insurance companiesLicensed to represent multiple insurance companies and offer a variety of policies
Work EnvironmentTypically employed by an insurance company or agencyWorks independently or for brokerage firms, representing multiple insurers
Employer & Industry UsageInsurance companies, agenciesBrokerage firms, independent agencies
Search & Comparison IntentLooking for agents to buy policies from specific insurersSeeking brokers who can compare policies across multiple insurers

While both Insurance Agents and Insurance Brokers assist clients with insurance policies, agents usually represent a single insurer, whereas brokers work independently to compare options across multiple companies. Understanding these differences helps you choose the right professional for your insurance needs.

Is being an insurance agent a good career?

Insurance agents sell policies to individuals and businesses, earning commissions and sometimes salaries. The career offers flexible schedules, opportunities for advancement, and requires strong communication and sales skills. Success often depends on building a client base and obtaining relevant licenses and certifications.

Is it hard to make money as an insurance agent?

Making money as an insurance agent can vary based on experience, sales skills, and the ability to build a client base. Income often depends on commissions from policies sold, and success typically requires persistence, networking, and ongoing training. Some agents earn substantial income, while others may find it challenging initially.
More about Insurance Agent jobs

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

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

What are popular job titles related to Insurance Agent jobs in Chicago, IL?

For Insurance Agent jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Insurance Agent jobs in Chicago, IL look for?

The top searched job categories for Insurance Agent jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Insurance Agent jobs?

Cities near Chicago, IL with the most Insurance Agent job openings:

Insurance Agent jobs near you
Infographic showing various Insurance Agent job openings in Chicago, IL as of August 2026, with employment types broken down into 68% Full Time, 13% Part Time, and 19% Contract. Highlights an 69% In-person, and 31% Remote job distribution, with an average salary of $67,035 per year, or $32.2 per hour.

Insurance Sales Agent

HealthMarkets, Inc.

Schaumburg, IL

Contractor

Re-posted 15 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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