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Remote Insurance Jobs in Chicago, IL (NOW HIRING)

Nexera

Entry Level Remote Insurance Sales

Chicago, IL · Remote

$1.5K - $3.2K/wk

... remote team. You'll help families find the right financial protection for their needs -- by phone and Zoom, from wherever you call home. No finance or insurance background needed. We'll train you and ...

Nexera

Entry Level Remote Insurance Sales

Chicago, IL · Remote

$1.5K - $3.2K/wk

... remote team. You'll help families find the right financial protection for their needs -- by phone and Zoom, from wherever you call home. No finance or insurance background needed. We'll train you and ...

HMG Careers

Sales Executive - Remote

Harvey, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

HMG Careers

Sales Executive - Remote

Waukegan, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

HMG Careers

Sales Executive - Remote

East Chicago, IN · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

HMG Careers

Sales Executive - Remote

Hammond, IN · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

Symmetry

Remote Work Sales Position

Chicago, IL · Remote

$60K - $200K/yr

We are looking for Remote Insurance Sales Representatives who can be trained to become a manager and lead in sales regions over the next nine months. Job Details: - Ability to understand and present ...

HMG Careers

Remote Benefits Sales Rep

Hammond, IN · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

HMG Careers

Remote Benefits Sales Rep

Waukegan, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

HMG Careers

Remote Benefits Sales Rep

East Chicago, IN · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

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Showing results 21-40

All JobsInsurance JobsRemote Insurance JobsRemote Insurance Jobs in Chicago, IL

Remote Insurance information

See Chicago, IL salary details

$24.2K

$60.9K

$100.4K

How much do remote insurance jobs pay per year?

As of Aug 10, 2026, the average yearly pay for remote insurance in Chicago, IL is $60,876.00, according to ZipRecruiter salary data. Most workers in this role earn between $41,700.00 and $79,800.00 per year, depending on experience, location, and employer.

What are common challenges in a remote insurance and how can they be addressed?

Remote insurance professionals often face challenges such as maintaining consistent client communication across time zones, staying up to date with rapidly changing regulations, and ensuring the privacy and security of sensitive client data. To address these, it is important to establish clear routines, leverage secure digital tools, and proactively communicate availability with both team members and clients. Staying connected with your team through virtual meetings and ongoing training can also help you remain informed and engaged. With the right tools and a proactive approach, these challenges can be successfully managed for a rewarding remote insurance career.

What is a remote insurance?

A Remote Insurance job involves working in the insurance industry from a remote location, typically from home. Roles can vary and may include sales, claims processing, underwriting, customer service, or adjusting. Professionals use digital tools to assess policies, handle client inquiries, process claims, and manage risk assessments. These jobs require strong communication skills, knowledge of insurance policies, and the ability to work independently. Many insurance companies offer remote positions to improve flexibility and reach a broader talent pool.

What skills and qualifications are needed for a remote insurance?

To excel in a Remote Insurance role, you need a solid understanding of insurance products, policy management, and compliance regulations, often supported by previous insurance experience or relevant certification (such as a state insurance license). Familiarity with CRM software, digital document management systems, and secure communication platforms is essential. Strong organizational skills, self-motivation, and the ability to communicate clearly and empathetically with clients set top performers apart. These skills are important to ensure effective client support, regulatory compliance, and productivity in a fully remote environment.

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 Remote Insurance jobs in Chicago, IL? For Remote Insurance jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Insurance jobs in Chicago, IL look for? The top searched job categories for Remote Insurance jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Insurance jobs? Cities near Chicago, IL with the most Remote Insurance job openings:
Remote Insurance jobs near you
Infographic showing various Remote Insurance job openings in Chicago, IL as of August 2026, with employment types broken down into 57% Full Time, and 43% Part Time. Highlights an 100% Remote job distribution, with an average salary of $60,876 per year, or $29.3 per hour.

Hiring Remote Insurance Brokers

The Edelson Agency

Chicago, IL • On-site, Remote

$70K - $90K/yr

Other

Re-posted just now

Job description

Insurance Broker
We are Seeking a motivated Insurance Broker to help clients find the right insurance coverage. Responsibilities include assessing client needs, recommending policies, managing applications, and providing ongoing support with claims and renewals. Affordable and detailed Leads. There is NO cold calling!! Ongoing in depth Training included.
Skills: Strong sales, customer service, and organizational abilities. Keeping a positive attitude and sincerity for clients needs.
Schedule: Remote work with flexible hours. Tailored to YOUR schedule
Join The Edelson Agency and build a rewarding career in insurance!
Apply now!

Apply