Insurance Sales Agent Jobs in Chicago, IL
Insurance Sales Agent jobs in Chicago are concentrated in the Loop, River North, and Schaumburg's corporate corridor, with strong demand from carriers, brokerages, and financial services firms. Employers hiring right now include State Farm, Kemper, and AMBA. See the openings below and apply to the ones that match your experience.
Find Insurance Sales Agent JobsOverview
Showing 5 of 87+ Insurance Sales Agent jobs
Sign-On Bonus Opportunity of up to $1,000*
Pay Range:
$15 - $17 / hour
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: We reimburse up to $15 a month to an employee for their gym
- 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 (mailto:employeerelations@confie.com)
Skills
Preferred- Bilingual - Spanish
Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights (https://www.eeoc.gov/poster) notice from the Department of Labor.
Sign-On Bonus Opportunity of up to $1,000*
Pay Range:
$15 - $17 / hour
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: We reimburse up to $15 a month to an employee for their gym
- 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 (mailto:employeerelations@confie.com)
Skills
Preferred- Bilingual - Spanish
Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights (https://www.eeoc.gov/poster) notice from the Department of Labor.
See All 87 Insurance Sales Agent Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Insurance Sales Agent JobsInsurance Sales Agent Job Market in Chicago
Who's Hiring
- State Farm25
- Kemper19K
- AMBA6A
- Aflac6
- Pioneer Agency6P
Insurance Sales Agent Jobs in Chicago: Frequently Asked Questions
How do I get an insurance sales agent job in Chicago?
The strongest path into Chicago's insurance market runs through the Loop and River North, where regional carriers, independent brokerages, and captive agencies concentrate. Candidates who hold a Property and Casualty or Life and Health license before applying move faster through hiring. A background in financial services, banking, or B2B sales is a genuine edge in Chicago's competitive market, and familiarity with commercial lines stands out among employers targeting business clients across the metro.
Which companies hire insurance sales agents in Chicago?
Companies currently hiring insurance sales agents in Chicago include State Farm, Kemper, and AMBA, per current listings on Migrate Mate as of August 2026. Chicago's market includes a mix of national carriers with regional offices, independent agencies serving small businesses, and specialty brokerages focused on commercial and employee benefits lines.
Are there remote insurance sales agent jobs in Chicago?
Yes, though remote availability is limited compared to purely analytical roles, since insurance sales often involves client meetings, prospecting events, and in-person relationship building. About 81% of insurance sales agent openings tied to Chicago are remote or hybrid as of August 2026, with remote arrangements more common for inside sales and renewal roles than for new-business development positions.
How can I get an insurance sales agent job in Chicago with little or no experience?
The most realistic entry point is a licensed customer service or inside sales role at a captive agency or regional carrier with a Chicago office, where new agents learn products and build a book under an established team. Chicago-area employers, including those in Schaumburg and Oak Brook's insurance corridors, regularly hire unlicensed candidates into paid training programs that cover exam prep. Completing your Illinois licensing exam before applying strengthens any entry-level application significantly.
Related Jobs in Illinois
See All 87 Insurance Sales Agent Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Insurance Sales Agent Jobs