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Health Insurance Broker Jobs in Chicago, IL (NOW HIRING)

RFQ - Insurance Broker

Chicago, IL ยท On-site

$40 - $100/hr

Medical (health insurance) * Dental * Vision * Life and AD&D * Disability (short- and long-term) * ... Multi-year benefits strategy development Brokerage Services * Marketing of all benefit lines ...

Broker

Chicago, IL ยท On-site

$150K - $175K/yr

Primary focus on Construction Casualty insurance products for contractors, owner/developers, and ... Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health ...

Broker

Chicago, IL

$150K - $175K/yr

Primary focus on Construction Casualty insurance products for contractors, owner/developers, and ... Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health ...

The Role As our Broker, you'll negotiate two-party domain transactions from start to finish ... Benefits: 401(k), dental insurance, health insurance, paid time off, vision insurance

The Role As our Broker, you'll negotiate two-party domain transactions from start to finish ... Benefits: 401(k), dental insurance, health insurance, paid time off, vision insurance

Principal - Insurance Brokerage

Lisle, IL ยท On-site

$154K - $193K/yr

Broker Integration with Carriers, Agents, and Reinsurers. * Digital transformation programs or ... Health and Dependent Care Reimbursement Accounts * Insurance (Accident, Critical Illness, Hospital ...

Property Broker - Wholesale

Hinsdale, IL ยท Hybrid

$76K - $100K/yr

Life and accident insurance * 401(K) and Roth options * Tax-advantaged accounts (HSA, FSA) * Educational expense reimbursement * Paid parental leave Other benefits include: * Digital mental health ...

Property Broker - Wholesale

Rolling Meadows, IL ยท Hybrid

$76K - $100K/yr

Life and accident insurance * 401(K) and Roth options * Tax-advantaged accounts (HSA, FSA) * Educational expense reimbursement * Paid parental leave Other benefits include: * Digital mental health ...

Property Broker - Wholesale

Chicago, IL ยท Hybrid

$78K - $103K/yr

Life and accident insurance * 401(K) and Roth options * Tax-advantaged accounts (HSA, FSA) * Educational expense reimbursement * Paid parental leave Other benefits include: * Digital mental health ...

Insurance Manager

Chicago, IL ยท On-site

$122 - $150/hr

Work closely with the Vice President of Commercial, General Counsel, and insurance broker to ... Health & WellnessFinancial BenefitsWork-Life Balance * Health Plans: Medical, Dental, Vision * Life ...

Insurance Manager

Chicago, IL ยท Hybrid

$136K - $195K/yr

Work closely with the Vice President of Commercial, General Counsel, and insurance broker to ... At Sargent & Lundy, we care about the health and well-being of our employees. Our commitment ...

Insurance Manager

Chicago, IL ยท Hybrid

$136K - $195K/yr

Work closely with the Vice President of Commercial, General Counsel, and insurance broker to ... Health & WellnessFinancial BenefitsWork-Life Balance * Health Plans: Medical, Dental, Vision * Life ...

Insurance Manager

Chicago, IL ยท On-site

$136K/yr

Work closely with the Vice President of Commercial, General Counsel, and insurance broker to ... Health & WellnessFinancial BenefitsWork-Life Balance * Health Plans: Medical, Dental, Vision * Life ...

Broker Integration with Carriers, Agents, and Reinsurers. * Digital transformation programs or ... Health and Dependent Care Reimbursement Accounts * Insurance (Accident, Critical Illness , Hospital ...

Full Senior Freight Broker The Opportunity: Company is hiring a Senior Freight Broker to join the ... Health insurance * Health savings account * Paid time off * Vision insurance Experience:

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Showing results 1-20

Health Insurance Broker information

See Chicago, IL salary details

$40.2K

$89.9K

$122.6K

How much do health insurance broker jobs pay per year?

As of Sep 6, 2026, the average yearly pay for health insurance broker in Chicago, IL is $89,853.00, according to ZipRecruiter salary data. Most workers in this role earn between $78,300.00 and $103,000.00 per year, depending on experience, location, and employer.

What does a health insurance broker do?

A health insurance broker is a licensed professional who helps individuals, families, and businesses find and purchase health insurance plans that best meet their needs and budgets. Brokers compare various policies from multiple insurance companies, explain coverage options, and assist clients with the application process. They also provide ongoing support, helping clients with renewals, claims, and any issues that arise during the policy period. Brokers are typically compensated by insurance companies, not by the clients they assist.

What are the key skills and qualifications needed to thrive as a health insurance broker?

To thrive as a Health Insurance Broker, you need a thorough understanding of insurance products, sales strategies, and regulatory compliance, typically supported by state licensure. Familiarity with customer relationship management (CRM) software, quoting tools, and insurance marketplace platforms is essential. Strong interpersonal skills, active listening, and the ability to explain complex policies clearly help brokers build trust and close sales. These skills and qualities are critical for matching clients to appropriate plans, ensuring legal compliance, and sustaining long-term client relationships.

What are some common challenges faced by health insurance brokers when assisting clients with plan selection?

Health Insurance Brokers often encounter challenges such as navigating the complexity of various insurance plans, staying updated with frequently changing regulations, and ensuring clients fully understand their coverage options. Balancing the diverse needs and budgets of clients while providing unbiased recommendations can be demanding. Additionally, brokers must handle administrative tasks, such as managing enrollments and resolving claim issues, all while maintaining strong relationships with both clients and insurance carriers.

What is the difference between Health Insurance Broker vs Health Insurance Agent?

AspectHealth Insurance BrokerHealth Insurance Agent
CredentialsMay require licensing and certifications; often independentLicensed to sell specific insurance products; typically affiliated with one company
Work EnvironmentIndependent or affiliated with brokerage firms; consults with clientsWorks for insurance companies or agencies; sells policies directly
Employer & Industry UsageUsed across multiple insurers; serves clients' best interestsEmployed by specific insurance companies; promotes their products
Search & Comparison IntentPeople compare brokers for independent advicePeople compare agents based on specific insurance options

In summary, health insurance brokers typically operate independently or with multiple insurers, offering broader options and personalized advice. Health insurance agents usually work for a single insurer, focusing on selling that company's policies. Both roles require licensing but differ in independence and employer structure.

Is health insurance brokering a good career?

Health insurance brokering is a viable career that involves helping clients select suitable insurance plans and requires strong sales, communication, and knowledge of insurance products. Success often depends on building a client base, obtaining necessary licenses, and staying updated on industry regulations and policies.

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

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

Infographic showing various Health Insurance Broker job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 19% Part Time, 5% Contract, and 1% Nights. Highlights an 92% Physical, 1% Hybrid, and 7% Remote job distribution, with an average salary of $89,923 per year, or $43.2 per hour.

RFQ - Insurance Broker

ReNEW Schools

Chicago, IL โ€ข On-site

$40 - $100/hr

Other

Medical, Dental, Vision, Life

Posted 5 days ago


Key responsibilities

  • Act as the District's broker of record and strategic advisor for employee benefit programs, including design, placement, and ongoing management.

  • Provide benefits consulting services such as market analysis, plan design recommendations, cost containment strategies, and renewal negotiations with carriers.

  • Assist with benefits administration support, including enrollment processes, benefits communication, and compliance with federal and state regulations.


Job description

REQUEST FOR QUALIFICATIONS (RFQ)

Employee Benefits Brokerage and Consulting Services

School City of East Chicago

1. OVERVIEW

The School City of East Chicago (โ€œDistrictโ€) is soliciting qualifications and proposals from experienced firms to provide comprehensive employee benefits brokerage and consulting services.

The selected firm will act as the Districtโ€™s broker of record and strategic advisor for the design, placement, administration, and ongoing management of employee benefit programs, including:

  • Medical (health insurance)
  • Dental
  • Vision
  • Life and AD&D
  • Disability (short- and long-term)
  • Voluntary/ancillary benefits

Current District Size: Approximately 600 employees (certified and classified staff)

2. CURRENT BENEFITS STRUCTURE

The District currently offers a suite of benefits including medical, dental, vision, and ancillary products to eligible employees. Administration is coordinated through the Human Resources Department.

Vendors should assume:

  • Multiple plan offerings may exist
  • Union and non-union employee groups
  • Employer and employee cost-sharing structures
  • Compliance with applicable federal and state regulations (ACA, COBRA, HIPAA, etc.)
3. SCOPE OF SERVICES

The selected broker/consultant will provide the following services:

Benefits Consulting & Strategy
  • Market analysis and benchmarking
  • Plan design recommendations
  • Cost containment strategies
  • Renewal negotiations with carriers
  • Multi-year benefits strategy development
Brokerage Services
  • Marketing of all benefit lines (medical, dental, vision, ancillary)
  • Carrier negotiations and placement
  • Recommendation of best-fit carriers and plan options
  • Transparent disclosure of commissions and fees
Benefits Administration Support
  • Assistance with enrollment processes (open enrollment and new hires)
  • Benefits communication materials and employee education
  • Eligibility and plan interpretation support
  • Coordination with third-party administrators and carriers
Compliance & Regulatory Support
  • Affordable Care Act (ACA) reporting and guidance
  • COBRA administration coordination
  • HIPAA compliance support
  • Section 125 plan compliance (currently managed by American Fidelity)
  • Legislative updates and impact analysis
Data Analytics & Reporting
  • Claims analysis and utilization reporting
  • Trend identification and forecasting
  • Custom reporting for leadership and board presentations
Technology & Tools
  • Benefits administration system (if applicable)
  • Employee self-service tools
  • Decision-support tools for employees
  • Integration with payroll/HR systems (if applicable)
4. PROPOSAL REQUIREMENTS A. Company Profile
  • Firm overview and history
  • Experience with Kโ€“12 public school districts
  • Credentials and certifications
  • References (preferably school districts of similar size)
B. Service Approach
  • Description of service model
  • Account management structure
  • Renewal and marketing strategy
  • Communication and employee engagement approach
  • Technology platforms offered
C. Compensation Proposal

Vendors must clearly disclose all compensation, including:

  • Commission structure (by line of coverage)
  • Fee-based alternatives (if applicable)
  • Any additional administrative or consulting fees
  • Bonus or incentive arrangements with carriers (if any)

Provide cost estimates under:

  • Commission-based model
  • Fee-based model (if available)
5. TRANSITION PLAN REQUIREMENTS

Vendors must outline a detailed transition plan including:

  • Broker-of-record transition process
  • Timeline for implementation
  • Communication strategy for employees
  • Coordination with current carriers and vendors
  • Open enrollment planning and execution
  • Risk mitigation and continuity of coverage
6. EVALUATION CRITERIA

Proposals will be evaluated based on:

  • Experience โ€“ Demonstrated success with Kโ€“12 clients
  • Cost Transparency โ€“ Clarity and competitiveness of compensation structure
  • Strategic Value โ€“ Ability to manage and reduce long-term benefit costs
  • Service Model โ€“ Responsiveness and support structure
  • Technology โ€“ Tools available for administration and employee engagement
  • References โ€“ Quality and relevance of client feedback
7. PROJECT TIMELINE

Milestone Date

RFQ Issued May 11, 2026

Questions Due May 30, 2026

Responses Due May 30, 2026

8. SUBMISSION INSTRUCTIONS

Submit proposals to:

School City of East Chicago

Joe Guardiola

Human Resources Coordinator

jguardiola@ecps.org

(219) 391-4100 ext. 12013

9. ADDITIONAL CONSIDERATIONS
  • Compliance with Indiana procurement laws is required
  • The District reserves the right to reject any or all proposals
  • Final contract terms are subject to negotiation
  • Vendors must disclose any conflicts of interest
  • Preference may be given to firms with public sector experience
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