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Remote Health Insurance Jobs in Chicago, IL (NOW HIRING)

NAPAA

Allstate Insurance Sales - Remote

Oak Park, IL · On-site +1

$51K - $130K/yr

Health insurance Take the next step in your professional journey-don't stay stuck in the same ... Salary Range: $51,000.00 - $130,000.00 per year This is a remote position. Compensation: $51,000.00 ...

AO Globe Life

Remote- Entry Level Manager

Chicago, IL · On-site +1

Comprehensive health insurance * Professional development opportunities * Performance-based bonuses Why Join Us? * Be part of an innovative, remote-first company culture * Work with cutting-edge ...

AO Globe Life

Remote- Entry Level Manager

Chicago, IL · On-site +1

Comprehensive health insurance * Professional development opportunities * Performance-based bonuses Why Join Us? * Be part of an innovative, remote-first company culture * Work with cutting-edge ...

AO Globe Life

Remote- Entry Level Manager

Chicago, IL · On-site +1

Comprehensive health insurance * Professional development opportunities * Performance-based bonuses Why Join Us? * Be part of an innovative, remote-first company culture * Work with cutting-edge ...

AO Globe Life

Remote- Entry Level Manager

Chicago, IL · On-site +1

Comprehensive health insurance * Professional development opportunities * Performance-based bonuses Why Join Us? * Be part of an innovative, remote-first company culture * Work with cutting-edge ...

AO Globe Life

Remote- Entry Level Manager

Chicago, IL · On-site +1

Comprehensive health insurance * Professional development opportunities * Performance-based bonuses Why Join Us? * Be part of an innovative, remote-first company culture * Work with cutting-edge ...

AO Globe Life

Remote- Entry Level Manager

Chicago, IL · On-site +1

Comprehensive health insurance * Professional development opportunities * Performance-based bonuses Why Join Us? * Be part of an innovative, remote-first company culture * Work with cutting-edge ...

Pioneer Agency

Insurance Agent

Chicago, IL · Remote

$50K - $75K/yr

We are a fast-growing insurance agency helping individuals and families with life, health, and ... Remote work opportunity with flexible scheduling * Competitive commission structure with bonus ...

Pioneer Agency

Insurance Agent

Chicago, IL · Remote

$50K - $75K/yr

Present and recommend a range of insurance products, including Life, Health, and Retirement options ... Remote work opportunities with flexible scheduling to fit your lifestyle. * Competitive commission ...

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Showing results 21-40

All JobsHealth Insurance JobsRemote Health Insurance JobsRemote Health Insurance Jobs in Chicago, IL

Remote Health Insurance information

See Chicago, IL salary details

$64.4K

$84.6K

$107.1K

How much do remote health insurance jobs pay per year?

As of Aug 16, 2026, the average yearly pay for remote health insurance in Chicago, IL is $84,574.00, according to ZipRecruiter salary data. Most workers in this role earn between $76,200.00 and $87,600.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a remote health insurance specialist, and why are they important?

To thrive as a Remote Health Insurance Specialist, you need a solid understanding of health insurance policies, claims processing, and regulatory compliance, often supported by a relevant degree or insurance license. Familiarity with CRM software, claims management systems, and digital communication tools is typically required. Strong attention to detail, problem-solving skills, and effective virtual communication set top performers apart. These skills ensure accurate claim handling, regulatory adherence, and excellent customer service in a remote work environment.

What are some common challenges of working in a remote health insurance role, and how can they be managed?

A common challenge in remote health insurance roles is maintaining effective communication with both clients and team members, as much of the work relies on virtual interactions. To manage this, professionals often use secure digital platforms and regularly scheduled video meetings to stay connected. Another challenge is staying updated with changing regulations and insurance policies, which requires proactive participation in ongoing training and close collaboration with compliance teams. Time management and self-motivation are also crucial, as remote work requires balancing multiple tasks independently throughout the day.

What is the difference between Remote Health Insurance vs Remote Medical Claims Processor?

AspectRemote Health InsuranceRemote Medical Claims Processor
Required CredentialsInsurance licenses, knowledge of health policiesMedical billing certifications, claims processing knowledge
Work EnvironmentHome-based, insurance companies or brokersHome-based, healthcare providers or insurance companies
Industry UsageInsurance industry, health plansHealthcare providers, insurance companies
Common Search/ComparisonRemote health insurance vs remote medical claims processor

Remote Health Insurance professionals focus on selling, managing, or advising on health insurance policies, often requiring licensing and industry knowledge. Remote Medical Claims Processors handle the review and processing of medical claims, typically needing billing certifications. Both roles are home-based and serve the healthcare and insurance sectors, but they differ in responsibilities and credentials.

What are remote health insurance jobs?

Remote health insurance jobs involve working in sales or providing customer service to policy-holders. As a work-from-home insurance agent, you sell healthcare policies to customers. You communicate with each customer by phone or internet to define their coverage needs, then help them select an insurance plan that has the benefits to meet those needs. Your duties can include assisting clients as they complete paperwork to obtain coverage and answering questions from new or existing policy-holders.

More about Remote Health Insurance jobs

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

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

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

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

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

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

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

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

Remote Health Insurance jobs near you
Infographic showing various Remote Health Insurance job openings in Chicago, IL as of August 2026, with employment types broken down into 5% Internship, 84% Full Time, 5% Temporary, and 6% Contract. Highlights an 100% Remote job distribution, with an average salary of $84,574 per year, or $40.7 per hour.

Allstate Insurance Sales - Remote

NAPAA

Oak Park, IL • On-site, Remote

$51K - $130K/yr

Full-time

Medical, Dental, Retirement

Re-posted 4 days ago

Job description

Benefits:
  • 401(k) matching
  • Competitive salary
  • Dental insurance
  • Employee discounts
  • Flexible schedule
  • Health insurance

Take the next step in your professional journey-don't stay stuck in the same income space!
We offer a flexible work schedule, a guaranteed base salary, and unlimited opportunities to earn big commissions in a thriving industry.
About the Opportunity
Do you hold a P&C Insurance Sales License and have experience selling Allstate Insurance? Amazing! Here's what you can look forward to:
  • Guaranteed Base Salary: Earn $36,000 annually, guaranteed.
  • Uncapped Commission Potential: Our commission program rewards top performers with an opportunity to triple your base salary.
  • Strong Marketing Support: Benefit from our proven CRM and agency-supplied leads through internet, mailers, and live call transfers.

Why Work With Us?
Passionate about sales and excel at building strong relationships, this role is the perfect fit for you. You'll enjoy:
  • Unlimited earning potential with lucrative, escalating commissions.
  • Growth opportunities in a dynamic, ever-changing industry.
  • Tools and resources that empower your success.

What We're Looking For
We need determined sales professionals who are leaders, closers, and fierce competitors ready to succeed in a high-energy environment.
Salary Range: $51,000.00 - $130,000.00 per year
This is a remote position.
Compensation: $51,000.00 - $130,000.00 per year
Becoming an Insurance Professional
Insurance Professionals go by many names: Brokers, Underwriters, Claims Representatives, Adjusters, Actuaries, etc. No matter the name, what they all have in common is a calling to help prepare people for the future.
NAPAA members understand the value of customers. They recognize that treating customers fairly and honestly is the only way to enjoy lasting success. Consumers can take comfort in knowing that, in terms of the qualities they seek in an insurance agent, NAPAA member agents are among the best there are.
As there is an upcoming worker shortage in the Insurance industry, the demand for Insurance Professionals is growing every day! Is this career right for you?
This agency is independently owned and operated. Your application will go directly to the agency, and all hiring decisions will be made by the management of the agency. All inquiries about employment at this agency should be made directly to the agency location, and not to NAPAA.

Apply