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Weekend Insurance Agent Jobs in Chicago, IL (NOW HIRING)

Chime Insurance Group is seeking a dedicated and knowledgeable Insurance Agent to join our dynamic team. As an Insurance Agent at Chime Insurance Group, you will play a crucial role in helping ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

We are seeking an exceptional entrepreneur to make a difference in Merrillville, IN and become our newest Shelter Insurance Agent. Do you have a desire to meet new people, develop new contacts, and ...

We are seeking an exceptional entrepreneur to make a difference in Crown Point, IN and become our newest Shelter Insurance Agent. Do you have a desire to meet new people, develop new contacts, and ...

This includes insurance to protect what they have today and financial products to help them prepare ... an Exclusive Agent. With Horace Mann's expertise and your ambition, together, we can help you ...

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 ...

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Weekend Insurance Agent information

See Chicago, IL salary details

$25.8K

$67K

$125.2K

How much do weekend insurance agent jobs pay per year?

As of Jul 15, 2026, the average yearly pay for weekend 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 jobs pay 4000 a week without a degree?

A Weekend Insurance Agent can potentially earn $4,000 or more per week through commissions and sales bonuses, especially with experience and a strong client base. Other high-paying roles without a degree include sales positions, real estate agents, and certain entrepreneurial ventures, but these often require skills, certifications, or licensing. Earnings vary based on performance, industry, and location.

Do insurance companies work on weekends?

Weekend insurance agents typically work during regular business hours, which are usually Monday through Friday. However, some insurance companies or agencies may offer weekend hours or have agents available for customer support on weekends, especially in roles that involve client service or sales. The specific schedule depends on the employer and the nature of the position.

Why do most insurance agents quit?

Most insurance agents quit due to challenges such as high competition, difficulty building a client base, and inconsistent income, especially during the initial stages of their career. The job often requires strong sales skills, self-motivation, and resilience, which can lead to burnout and turnover if these are not developed or maintained.

How many hours a week do insurance agents work?

Insurance agents typically work full-time hours, averaging around 40 hours per week, though some may work evenings or weekends to meet client needs. Part-time positions are also available, with hours varying based on employer and individual schedule preferences.

What is the difference between Weekend Insurance Agent vs Part-Time Insurance Agent?

AspectWeekend Insurance AgentPart-Time Insurance Agent
CredentialsLicensing required, similar certificationsLicensing required, similar certifications
Work EnvironmentPrimarily weekend hours, flexible scheduleFlexible hours, may include weekdays and weekends
Employer & Industry UsageInsurance agencies, brokersInsurance agencies, brokers
Search & Comparison IntentFocus on weekend availability and part-time rolesBroader part-time roles, including weekdays

Weekend Insurance Agents typically work primarily on weekends, offering flexible scheduling for clients. Part-Time Insurance Agents may work during weekdays or weekends, with varied hours. Both roles require similar licensing and certifications, but the main difference lies in their scheduling focus and availability.

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 job categories do people searching Weekend Insurance Agent jobs in Chicago, IL look for? The top searched job categories for Weekend Insurance Agent jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Weekend Insurance Agent jobs? Cities near Chicago, IL with the most Weekend Insurance Agent job openings:
Infographic showing various Weekend Insurance Agent job openings in Chicago, IL as of July 2026, with employment types broken down into 91% Full Time, 7% Part Time, and 2% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution, with an average salary of $66,982 per year, or $32.2 per hour.

Insurance Agent

Chime Insurance Group

Frankfort, IL • Remote

Full-time

Medical, Life

Posted 18 days ago


Job description

Chime Insurance Group is seeking a dedicated and knowledgeable Insurance Agent to join our dynamic team. As an Insurance Agent at Chime Insurance Group, you will play a crucial role in helping clients protect their assets, lives, and futures by providing expert guidance on various insurance products.

Requirements

Sell Life, Health & Medicare coverage remotely with a growing independent agency. 1099 contractor: $50,000 base + uncapped commission, weekly direct deposits, and free pre-screened inbound leads (Medicare A&B/Medicaid).

Requires an active Life & Health license in AZ, IL, MD, MI, NC, NY, OH, PA, TN, TX, or VA. Medicare/AHIP experience preferred; bilingual encouraged. Sell life insurance in any state you're licensed in.

Total flexibility, AI-powered tools, and ongoing training and support — seasonal or year-round.

Onboard now to start selling by Sept 1 and maximize AEP/OEP earnings.

Benefits

Remote work.

$50,000 plus commission

Onboard now to start selling by Sept 1 and maximize AEP/OEP earnings. Apply today.