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Remote 1099 Insurance Agent Jobs in Chicago, IL (NOW HIRING)

Big I Illinois

Insurance Agent

IL · On-site +1

$60K - $150K/yr

... remote position. Compensation: $60,000.00 - $150,000.00 per year YOUR FUTURE as an Independent ... Insurance Agent Starts Here If you're looking for a career that offers flexibility, job stability ...

GIA Legacy Planning

Life Insurance Agent

Crown Point, IN · On-site +1

Life Insurance Agent Location: Work from Home Job Type: Full-Time/Part-Time/Commission-Based About ... Flexible work schedule (remote positions) * Comprehensive training and mentorship programs * Access ...

Lone Star Careers

Remote Insurance Agent

Joliet, IL · Remote

$69K/yr

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

Empire State Careers

Remote Insurance Agent

Aurora, 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 ...

Lone Star Careers

Remote Insurance Agent

Elgin, IL · Remote

$69K/yr

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

Lone Star Careers

Remote Insurance Agent

Chicago, IL · Remote

$69K/yr

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

Lone Star Careers

Remote Insurance Agent

Gary, IN · Remote

$69K/yr

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

HMG Careers

Remote Insurance Agent

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 ...

HMG Careers

Remote Insurance Agent

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 ...

Empire State Careers

Remote Insurance Agent

Elgin, 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 ...

Empire State Careers

Remote Insurance Agent

Gary, 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 ...

Empire State Careers

Remote Insurance Agent

Joliet, 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 ...

HMG Careers

Remote Insurance Agent

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 ...

Lone Star Careers

Remote Insurance Agent

Aurora, IL · Remote

$69K/yr

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

HMG Careers

Remote Insurance Agent

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 ...

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All Jobs1099 Insurance Agent JobsRemote 1099 Insurance Agent JobsRemote 1099 Insurance Agent Jobs in Chicago, IL

Remote 1099 Insurance Agent information

See Chicago, IL salary details

$25.8K

$67K

$125.2K

How much do remote 1099 insurance agent jobs pay per year?

As of Sep 1, 2026, the average yearly pay for remote 1099 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 is a Remote 1099 Insurance Agent?

A Remote 1099 Insurance Agent is an independent contractor who sells insurance policies from a remote location, rather than working onsite at an agency or company office. The '1099' refers to the IRS tax form used for independent contractors, meaning they are not employees but self-employed individuals responsible for their own taxes. These agents typically earn commissions on the policies they sell and have flexibility in setting their own schedules. They often work with multiple insurance companies and must handle their own marketing, client acquisition, and administrative tasks.

What are the key skills and qualifications needed to thrive as a remote 1099 insurance agent?

To thrive as a Remote 1099 Insurance Agent, you need strong sales acumen, comprehensive knowledge of insurance products, and a valid state insurance license. Familiarity with CRM software, quoting systems, and digital communication tools is typically required. Excellent self-motivation, communication, and customer relationship skills help agents stand out in a remote, commission-driven environment. These abilities are crucial for effectively building a client base, meeting sales targets, and succeeding independently in a competitive market.

What are some common challenges faced by remote 1099 insurance agents, and how can they be addressed?

Remote 1099 Insurance Agents often face challenges such as managing their own schedule, generating leads independently, and staying motivated without direct supervision. Building a strong daily routine, leveraging digital marketing strategies, and actively participating in virtual networking or training sessions can help overcome these hurdles. Additionally, effective communication with clients and insurance carriers is crucial, so utilizing reliable technology and CRM tools is highly recommended. Proactively seeking mentorship or support from online agent communities can also provide valuable guidance and encouragement.

What is the difference between Remote 1099 Insurance Agent vs Remote 1099 Insurance Broker?

AspectRemote 1099 Insurance AgentRemote 1099 Insurance Broker
CredentialsLicenses required for specific insurance typesSame as Insurance Agent, plus ability to represent multiple carriers
Work EnvironmentIndependent, remote salesIndependent, remote sales with broader carrier access
Employer/Industry UsageOften contracted directly with insurance companies or agenciesTypically contracted with multiple carriers or as an independent broker
Search/Comparison IntentFocus on individual insurance sales rolesFocus on roles involving multiple carrier representation

While both roles operate remotely as 1099 independent contractors, a Remote 1099 Insurance Agent primarily sells policies for specific insurance companies, requiring relevant licenses. A Remote 1099 Insurance Broker, on the other hand, can represent multiple carriers, offering clients broader options. The key difference lies in carrier access and licensing scope, impacting the sales approach and client offerings.

What are the most commonly searched types of 1099 Insurance Agent jobs in Chicago, IL?

The most popular types of 1099 Insurance Agent jobs in Chicago, IL are:

What are popular job titles related to Remote 1099 Insurance Agent jobs in Chicago, IL?

For Remote 1099 Insurance Agent jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote 1099 Insurance Agent jobs in Chicago, IL look for?

The top searched job categories for Remote 1099 Insurance Agent jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote 1099 Insurance Agent jobs?

Cities near Chicago, IL with the most Remote 1099 Insurance Agent job openings:

Remote 1099 Insurance Agent jobs near you
Infographic showing various Remote 1099 Insurance Agent job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, and 5% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $66,982 per year, or $32.2 per hour.

Financial Representative (Remote)

Chicago, IL • Remote

Synergy Financial
11 - 50 employees
Learn more about Synergy Financialexternal

$75K - $100K/yr

Full-time

Medical, Life, Retirement

Posted 16 days ago

Job description

???? Remote Insurance & Financial Services Agent (Licensed Preferred) – Commission-Based | Synergy Financial

Location: Remote (U.S. Based)
Employment Type: 1099 Contract | Commission-Only
Industry: Financial Services, Life Insurance, Annuities, Wealth Management, Consulting




✅ Are You an Entrepreneurial Professional with a Passion for Financial Freedom?
Synergy Financial is one of the fastest-growing agencies in financial services, and we’re actively hiring licensed insurance agents, financial professionals, and business-minded entrepreneurs who are looking for a high-impact remote opportunity with uncapped income potential.
If you’re already life and health licensed, or hold Series 6, 63, 65, or 7 licenses — or you're seeking a career change into insurance and financial services — we want to connect with you.





???? What We Offer:
Remote, work-from-home flexibility – control your schedule
Performance-based commissions – no cap on earnings
Hands-on mentorship and training
Opportunities to help families with real financial solutions (life insurance, annuities, rollovers, living benefits, etc.)
A clear promotion track and leadership development path
Access to a diverse client base and multi-lingual markets





???? Key Responsibilities:
Educate families and individuals on life insurance, annuities, 401(k) rollovers, college funding, and debt solutions
Consult with clients on retirement strategies, legacy planning, and tax-advantaged solutions
Grow your book of business and manage client relationships
Option to build and lead your own remote team with leadership compensation
Work closely with senior field trainers and certified mentors





???? Ideal Candidates Have:
An active Life & Health Insurance License (or willingness to obtain one quickly)
Series 6, 63, or 65 licenses are a huge plus (but not required)
Sales, customer service, or consulting experience in financial services
Strong communication and presentation skills
A self-motivated, entrepreneurial mindset
Bilingual capabilities (Spanish, Tagalog, Mandarin, etc.) a strong asset





???? Compensation:
This is a commission-only 1099 opportunity with an On-Time-Earnings Estimate (OTE) of $75,000 - $100,000+ annually for full-time, focused agents. Top agents earn well beyond six figures through team overrides and advanced compensation contracts.





???? Who We Are:
Synergy Financial is a mission-driven agency powered by Meraki Group Endeavors, our national talent screening partner. We are part of a movement to increase financial literacy, protect families, and build generational wealth through scalable business models and mentorship.
We believe in financial education before financial products — and we're committed to helping people win, both as clients and as agents.





???? Ready to Level Up Your Life and Career?
If you're driven, coachable, licensed, and hungry to make a difference — this is not just another sales job. It’s a calling. It’s a career path that rewards performance, leadership, and impact.
???? Apply Now to be pre-screened by our JAG-LOGiC team. Your financial future starts today.

Keywords for Optimization (Do Not Delete):
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