Health Insurance Jobs in Chicago, Illinois

42,828 open positions · Updated daily

Looking for Health Insurance jobs in Chicago, Illinois? Browse our curated listings with transparent salary information to find the perfect Health Insurance position in the Chicago, Illinois area.

Over The Road-Class A Driving

Company: West Side Transport

Location: Illinois

Posted Aug 01, 2025

6+ Months of Class A Driving. We also offer Health, Dental, Vision, Life Insurance, and 401k with company match.

Service Technician/Machinist

Company: Goulds Pumps IPG LLC

Location: Chicago, IL

Posted Aug 01, 2025

Building on centuries of pump design experience, PRO Services provides an array of services focuses on reducing equipment total cost of ownership and increasing…

CDL A Midwest Drivers Only Reset at Home

Company: MNS1 EXPRESS INC

Location: Chicago, IL

Posted Aug 01, 2025

Must have at least 2 years of commercial driving experience. Must have at least 2 years of commercial driving experience. 2500-3000 Miles Per Week.

Flex-Home All Weekend-Class A Driver

Company: West Side Transport

Location: Illinois

Posted Aug 01, 2025

Network of devoted support and service teams. 6+ Months of Class A Experience. We also offer Health, Dental, Vision, Life Insurance, and 401k with company match…

Regional-Class A Driving

Company: West Side Transport

Location: Illinois

Posted Aug 01, 2025

$1,200 a week minimum pay commitment. Professional and caring Safety and Operational culture. 6+ Months of Class A Driving.

CDL A Company Truck Driver Regional

Company: Go-To Transport, Inc

Location: Chicago, IL

Posted Aug 01, 2025

Must have CDL A license. Clean driving record , no more than 1 accident in last 12 months, no more than 3 in the last 36 months. $10,000 life insurance policy.

Senior Associate Brand Manager - Goodnites®

Company: Kimberly-Clark

Location: Chicago, IL

Posted Aug 01, 2025

Diverse income protection insurance options to protect yourself and your family in case of illness, injury, or other unexpected events. In this role, you will:

CDL-A Truck Driver-Increased Driver Pay

Company: PAM Transport, Inc.

Location: Chicago, IL

Posted Aug 01, 2025

Retirement plan w/ company matching. Retirement plan w/ company matching Great health, dental insurance. Retirement plan w/ company matching.

CDL A Tanker Truck Driver - Home Weekly

Company: Andrews Logistics Inc.

Location: Chicago, IL

Posted Aug 01, 2025

Paid training for dry van or flatbed drivers with clean MVR’s and good work history. Wage Range: 0.68 - 0.74 per mile. 401(k) With Company Matching.

CDL A Flatbed Truck Driver - Home Weekly

Company: AWL Transport Inc. dba TLX

Location: Chicago, IL

Posted Aug 01, 2025

2 Years Verifiable Driving Experience w/ Steel coil & heavy haul experience. Must be 22 Years of Age. OUR FLATBED TRUCK DRIVERS EARN UP TO $80,000 PER YEAR –…

CDL A Local Company Truck Driver Chicago

Company: Kutzler YMX MC, LLC

Location: Chicago, IL

Posted Aug 01, 2025

Kutzler YMX Local CDL A Company Shuttle Truck Drivers Earn Great Hourly Pay and Home Daily in South Side Chicago, IL! Based on 40 Hour Work Week, 8 Hour Shifts.

Kindergarten Apprentice

Company: Acero Charter Schools, Inc.

Location: Chicago, IL

Posted Aug 01, 2025

Possess valid Illinois Paraprofessional Educator License (PARA) or equivalent (required). Clearly and accurately communicate with administration, colleagues,…

Frequently Asked Questions

What are typical salary ranges by seniority in Health Insurance?
Entry‑level analysts earn $55k–$75k, mid‑level roles $80k–$110k, senior positions $115k–$150k, and directors or VP levels range from $160k to $200k. Pay varies by region; for example, New York City salaries are often 20% higher than national averages.
Which skills and certifications are required?
Key technical skills include SQL, SAS, R, Tableau, and HL7 for data integration. Certification requirements often involve SOA or CAS actuarial exams, HIPAA‑compliance credentials, Guidewire Underwriting Certification, PMP for project managers, and financial certifications like CPA or CMA for finance roles.
Is remote work available in Health Insurance roles?
Yes—about 70% of positions offer fully remote or hybrid options. Major carriers such as UnitedHealth, Anthem, Humana, and CVS Health have formal telecommuting policies, especially for data‑analysis, product‑management, and compliance roles.
What are common career progression paths?
Typical trajectories move from junior analyst to senior analyst, then to manager, director, and VP. Progression often requires additional certifications (e.g., actuarial exams, PMP), cross‑functional experience, and proven leadership in projects like claims automation or value‑based care initiatives.
What industry trends should Health Insurance professionals watch?
Key trends include AI‑driven fraud detection, telehealth expansion, value‑based care models, regulatory updates to the ACA and Medicare Advantage, data‑privacy enforcement (HIPAA, GDPR), cybersecurity investments, and ESG‑aligned underwriting practices.

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