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Freelance Insurance Jobs in Chicago, IL (NOW HIRING)

Siege Media

Freelance Financial Content Writer

Chicago, IL · Remote

$21.75 - $28/hr

We currently have a spot open for a talented Freelance Financial Content Writer to help us continue ... insurance, and mortgage loans * Experience writing for the web, with a focus on digital content ...

Siege Media

Freelance Financial Content Writer

Chicago, IL · On-site +1

$22 - $28/hr

We currently have a spot open for a talented Freelance Financial Content Writer to help us continue ... insurance, and mortgage loans * Experience writing for the web, with a focus on digital content ...

Sourcebooks

Production Editor - Children's

Naperville, IL · On-site

$62K - $66K/yr

You'll partner with editorial, managing editorial, manufacturing, design, freelancers, and other ... Our range of benefits include, but are not limited to, Medical/Prescription Drug Insurance, Dental ...

BGBx

VP, Associate Creative Director, Art

Chicago, IL

$170K - $200K/yr

Recommends and directs freelance contributors * Engages in any personal development necessary to ... Our benefits package typically includes health care insurance, retirement plans, generous paid time ...

Publicis Groupe Holdings B.V

Copy Editor

Chicago, IL · Hybrid

$53K - $79K/yr

We also offer medical and voluntary benefits to our freelancers and temporary employees. Voluntary benefit options include supplemental medical insurance, transportation, and parking benefits, legal ...

Headkount

Brand Advisor - Chicago

Chicago, IL

$27 - $31/hr

... a freelance or contractor role. You'll receive the benefits and protections of employee status, including workers' compensation coverage, unemployment insurance eligibility based on state, and ...

Headkount

Brand Advisor - Chicago

Chicago, IL · On-site

$27 - $31/hr

... a freelance or contractor role. You'll receive the benefits and protections of employee status, including workers' compensation coverage, unemployment insurance eligibility based on state, and ...

Headkount

Brand Advisor - Chicago (West)

Chicago, IL

$27 - $31/hr

... a freelance or contractor role. You'll receive the benefits and protections of employee status, including workers' compensation coverage, unemployment insurance eligibility based on state, and ...

Headkount

Brand Advisor - Chicago (West)

Chicago, IL

$27 - $31/hr

... a freelance or contractor role. You'll receive the benefits and protections of employee status, including workers' compensation coverage, unemployment insurance eligibility based on state, and ...

Headkount

Brand Advisor - Chicago (West)

Naperville, IL

$30 - $35/hr

... a freelance or contractor role. You'll receive the benefits and protections of employee status, including workers' compensation coverage, unemployment insurance eligibility based on state, and ...

Headkount

Brand Advisor - Chicago (West)

Oak Brook, IL

$30 - $35/hr

... a freelance or contractor role. You'll receive the benefits and protections of employee status, including workers' compensation coverage, unemployment insurance eligibility based on state, and ...

Kehoe Designs Inc

Event Technical Support

Chicago, IL · On-site

$25 - $28/hr

Coordinate event staffing, schedules, freelancers, and crew communication. * Assist with recruiting ... Health Insurance: Medical, dental, and vision insurance options available full-time. * Retirement ...

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All JobsInsurance JobsFreelance Insurance JobsFreelance Insurance Jobs in Chicago, IL

Freelance Insurance information

See Chicago, IL salary details

$15

$49

$136

How much do freelance insurance jobs pay per hour?

As of Aug 23, 2026, the average hourly pay for freelance insurance in Chicago, IL is $49.15, according to ZipRecruiter salary data. Most workers in this role earn between $25.00 and $63.65 per hour, depending on experience, location, and employer.

What is a freelance insurance agent?

A freelance insurance agent is an independent professional who helps clients find, purchase, and manage insurance policies such as health, life, auto, or property insurance. Unlike agents who work for a single insurance company, freelance agents can represent multiple insurers, offering clients a broader range of options. They earn commissions based on the insurance policies they sell and may also provide ongoing customer service. Freelance insurance agents are responsible for prospecting clients, understanding their needs, and recommending suitable coverage. They typically have flexible schedules and operate their own businesses.

What are the key skills and qualifications needed to thrive as a freelance insurance agent?

To thrive as a Freelance Insurance Agent, you need in-depth knowledge of insurance products, strong sales abilities, and appropriate state licensing. Familiarity with customer relationship management (CRM) software, quoting tools, and digital marketing platforms is typically required. Excellent communication, self-motivation, and networking skills help build trust and expand your client base. These competencies are crucial for meeting client needs, maintaining compliance, and achieving sales targets in a competitive, independent environment.

How do freelance insurance professionals typically find clients and manage their workload?

Freelance insurance professionals often find clients through networking, referrals, online platforms, and partnerships with agencies or brokers. Managing workload usually involves balancing multiple client accounts, staying organized with schedules and deadlines, and using customer relationship management (CRM) tools. Since freelancers set their own hours, strong self-discipline and time management skills are essential. Building long-term relationships and maintaining industry certifications can also help sustain and grow a freelance insurance business.

What is the difference between Freelance Insurance vs Insurance Agent?

AspectFreelance InsuranceInsurance Agent
CredentialsVaries; often requires licensing depending on services offeredRequires state licensing and certification
Work EnvironmentSelf-employed, remote or independentEmployed by an insurance company or agency
Employer & Industry UsageIndependent contractors serving multiple clientsRepresenting specific insurance companies
Search & Comparison IntentUnderstanding freelance insurance options and licensingComparing insurance policies and agent services

Freelance Insurance professionals operate independently, often offering a range of insurance-related services without being tied to a single company. Insurance Agents typically work for specific insurers, focusing on selling and managing policies for their employer. Both roles require licensing, but their work environments and client interactions differ significantly.

Do independent insurance agents make good money?

Independent insurance agents can earn a wide range of income depending on their sales performance, client base, and commission rates, which typically range from 10% to 20% of policy premiums. Successful agents with strong networks and sales skills can make a substantial income, but earnings often depend on experience, specialization, and market conditions.

How do freelance insurance workers get insurance?

Freelance insurance workers typically obtain insurance through professional associations, independent insurance agents, or by purchasing individual policies such as health, liability, or disability insurance. They may also use online insurance marketplaces to compare plans and find coverage suited to their freelance work and personal needs.

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

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

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

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

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

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

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

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

Freelance Insurance jobs near you
Infographic showing various Freelance Insurance job openings in Chicago, IL as of August 2026, with employment types broken down into 62% Full Time, 26% Part Time, and 12% Contract. Highlights an 100% In-person job distribution, with an average salary of $102,222 per year, or $49.1 per hour.

Freelance Financial Content Writer

Siege Media

Chicago, IL • Remote

$21.75 - $28/hr

Contractor

Re-posted 16 days ago

Job description

Siege Media is a growing and remote-first GEO agency! We are nationally recognized on Inc.’s Best Workplaces list and Inc. 5000 list, highlighting the 5000 fastest-growing private companies. Interested in working with the Siege team? We currently have a spot open for a talented Freelance Financial Content Writer to help us continue to deliver great content for our world-class clients.

Learn more about working at Siege by experiencing our culture on Instagram and checking out our work on Dribbble!

Siege Media values diversity. We encourage people of color, LGBTQIA+ folks, veterans, parents and those with disabilities to apply. We are committed to helping all people succeed at Siege. If you require reasonable accommodation to complete our application or interview process, please let us know.

Responsibilities

  • Write comprehensive articles on a variety of topics including investing, taxes, debt, credit, budgeting, and banking
  • Demonstrate the ability to adapt tone and complexity of a piece to speak to the correct audience, as well as align with relevant style guides
  • Hit client SEO traffic goals month over month by creating content that ranks and/or generates organic links
  • Have a firm grasp on writing effective titles for improved CTR and the press
  • Demonstrate the ability to implement feedback from editors, clients, and teammates
  • Deliver a reliable, solutions-oriented approach to growing the online presence of our clients
Required Skills
  • 2-3 years of experience as a content writer, writing finance-specific content (ideally published on reputable news sites or industry blogs, such as Investopedia, Nerd Wallet, Forbes, etc.)
  • Extensive knowledge of niche topics including digital currency, financial planning, passive income/side hustles, insurance, and mortgage loans
  • Experience writing for the web, with a focus on digital content including long-form guides, how-tos, software/tool roundups, comparison posts, trend reports, and other thought leadership content
  • Strong interpersonal skills, with ability to form productive working relationships in a remote environment
  • Strong project management skills, with ability to handle multiple projects while still working effectively
  • Ability to set priorities, meet deadlines, and work independently
  • Close attention to detail and a heavy focus on creating quality content
  • Proven ability to generate creative ideas that attract attention on the web
Suggested Skills
  • 4-year university degree in finance, economics, or a related field
  • Intermediary SEO knowledge with a working knowledge of SEO tools and how they can be used to improve client websites
  • Experience collaborating with design teams and giving guidance on design and UX best practices

Please plan to upload the following information during the application process:

  1. Your resume
  2. A short introduction/cover letter
  3. A link to your portfolio with at least 3 writing samples that show diversity in complexity within the finance vertical

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