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

Pitch Health Solutions

Health Insurance Agent

Joliet, IL · Remote

$18 - $20/hr

Remote Health Insurance Agent About Pitch Health Solutions Pitch Health Solutions is a rapidly growing national agency specializing in Medicare Advantage, Final Expense , and more, giving you ...

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All JobsInsurance Agent JobsWeekend Insurance Agent JobsWeekend Insurance Agent Jobs in Chicago, IL

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 Aug 9, 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.

Why do so many weekend insurance agents quit?

Weekend insurance agents often leave the role due to limited hours, lower pay, and lack of career advancement opportunities. The part-time schedule can also lead to job insecurity and difficulty balancing work with personal commitments, contributing to higher turnover rates.

Do weekend insurance agents work on weekends?

Weekend insurance agents typically work during weekends as part of their schedule, especially if they serve clients who are available outside regular weekday hours. Their work may include handling claims, providing customer service, or selling policies, often requiring flexibility to meet client needs. The specific schedule depends on the employer and the role's responsibilities.

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 are popular job titles related to Weekend Insurance Agent jobs in Chicago, IL? For Weekend Insurance Agent jobs in Chicago, IL, the most frequently searched job titles 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:
Weekend Insurance Agent jobs near you
Infographic showing various Weekend Insurance Agent job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 20% Part Time, and 5% 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 Sales Agent - Customer Service

Freeway Insurance

Chicago, IL

Full-time

Medical, Dental, Vision, Life, Retirement

Re-posted 3 days ago

Freeway Insurance rating

8.2

Company rating: 8.2 out of 10

Based on 12 frontline employees who took The Breakroom Quiz

141st of 304 rated insurance

Job description

Our Perks:

  • Unlimited/Uncapped commission
  • Lucrative incentive sales plans, bonuses and sales contests
  • No Cold Calling- We have a high volume of inbound sales leads and walk in traffic
  • Comprehensive paid training and licensing with continuous on-going training and mentorship
  • Recognition culture
  • Comprehensive Benefits package including medical, dental, vision and life insurance
  • Retirement Plan: A 401K plan with a percentage of company-matched contributions
  • Fitness: Discount gym membership to over 12,200 fitness centers and 9,300 on-demand workout videos including a $15 a month reimbursement.
  • Employee Assistance Program: Confidential assistance to you or anyone in your household who is experiencing personal or professional problems — at no cost
  • Extra Perks: Access to disability, hospital indemnity, health advocate program, universal life, critical illness, and accident insurance plans. We even offer pet insurance

Our Company:

Confie and its family of companies - Freeway, Baja, Bluefire & others - is one of the largest privately held insurance brokers in the United States and has been ranked the #1 Personal Lines Leader by the Insurance Journal for the seventh straight year!. With over 800 retail store locations to choose from nationwide, we encourage you to take your career and income potential to new heights! We are proactively looking for bright, talented, and motivated individuals who are goal oriented and excited for career advancement. Come Grow With Us!

What You Will Do:

As an Insurance Agent you will be responsible primarily for the sale of nonstandard auto insurance to new and existing customers.

  • Solicit new business and maintain current business levels in order to achieve or exceed sales production goals.
  • Expand business by proactively building relationships with existing customers to meet the agreed upon production goals.
  • Accurate accounting of all currency transactions as well as timely delivery of deposits to the bank with scanned documentation in agency management system.
  • Connects very quickly; builds and leverages client relationships. Ability to educate and advise the customer on which products best fit their needs

The Perfect Match:

  • Personal Lines or Property and Casualty license preferred (but not required)
  • Bilingual in English and Spanish preferred
  • Sales or customer service experience
  • High School Diploma or GED
  • Ability to build relationships with sales customers
  • Excellent follow-up and multi-tasking skills
  • Ambitious professional motivated by opportunity for advancement
  • Excellent written and verbal communication skills

Insurance Sales
Insurance Agent
Hiring Immediately
Freeway Auto Insurance

As permitted by applicable law and from time-to-time, Confie may use a computer system that has elements of artificial intelligence to help make decisions about your employment, including recruitment, hiring, renewal of employment, or the terms and conditions of your employment. Employees with questions about Confie’s use of these computer systems should contact Human Resources at employeerelations@confie.com  

What Freeway Insurance employees say

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Benefits

Hours and flexibility

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