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Insurance Agent Jobs in Chicago, IL (NOW HIRING)

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Insurance Agent information

See Chicago, IL salary details

$25.8K

$67K

$125.3K

How much do insurance agent jobs pay per year?

As of Aug 19, 2026, the average yearly pay for insurance agent in Chicago, IL is $67,035.00, according to ZipRecruiter salary data. Most workers in this role earn between $45,900.00 and $79,400.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as an insurance agent, and why are they important?

To thrive as an Insurance Agent, you need a solid understanding of insurance products, sales techniques, and relevant regulations, often supported by a state insurance license. Familiarity with customer relationship management (CRM) software and quoting systems is typically required. Strong interpersonal skills, active listening, and persuasive communication help agents build trust and effectively address client needs. These competencies are vital for meeting sales targets, ensuring compliance, and maintaining long-term client relationships.

What are some common challenges insurance agents face when building their client base, and how can they overcome them?

Insurance Agents often encounter challenges such as establishing trust with new clients, differentiating themselves in a competitive market, and managing client rejections. To overcome these obstacles, agents typically focus on building strong relationships through personalized service, maintaining up-to-date product knowledge, and leveraging networking opportunities. Successful agents also use digital marketing tools and referrals to expand their reach and consistently follow up with prospects to nurture long-term relationships.

What is the difference between Insurance Agent vs Insurance Broker?

AspectInsurance AgentInsurance Broker
CredentialsLicensed to sell policies for specific insurance companiesLicensed to represent multiple insurance companies and offer a variety of policies
Work EnvironmentTypically employed by an insurance company or agencyWorks independently or for brokerage firms, representing multiple insurers
Employer & Industry UsageInsurance companies, agenciesBrokerage firms, independent agencies
Search & Comparison IntentLooking for agents to buy policies from specific insurersSeeking brokers who can compare policies across multiple insurers

While both Insurance Agents and Insurance Brokers assist clients with insurance policies, agents usually represent a single insurer, whereas brokers work independently to compare options across multiple companies. Understanding these differences helps you choose the right professional for your insurance needs.

Is an insurance agent a good career?

An insurance agent is a sales professional who helps clients select insurance policies and provides ongoing service. The career offers flexible hours, commission-based income, and requires strong communication and sales skills, with success often dependent on building a client base and obtaining relevant licenses. It can be a stable and rewarding career for those interested in finance and customer service.

Is it hard to make money as an insurance agent?

Making money as an insurance agent can vary based on experience, sales skills, and the ability to build a client base. Income often depends on commissions from policies sold, and success typically requires persistence, networking, and product knowledge. Some agents earn substantial income, while others may find it challenging initially.
More about Insurance Agent jobs

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 Insurance Agent jobs in Chicago, IL?

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

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

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

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

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

Insurance Agent jobs near you
Infographic showing various Insurance Agent job openings in Chicago, IL as of August 2026, with employment types broken down into 100% Full Time. Highlights an 75% In-person, and 25% Remote job distribution, with an average salary of $67,035 per year, or $32.2 per hour.

Insurance Sales Agent - Customer Service

Freeway Insurance

Chicago, IL • On-site

Full-time

Medical, Dental, Vision, Life, Retirement

Re-posted 14 days ago

Freeway Insurance rating

8.2

Company rating: 8.2 out of 10

Based on 12 frontline employees who took The Breakroom Quiz

144th of 310 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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