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.

Security Agent

Company: SOS Enterprises LLC

Location: Chicago, IL

Posted Aug 11, 2025

All agents must be able to obtain licensing through the Illinois Department of Financial and Professional Regulation, are required to score a minimum of 95%…

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Construction Management, Project Manager -- Superintendent, Chicago

Company: Bushman Construction Management

Location: Chicago, IL

Posted Aug 10, 2025

0-5+years field experience in commercial construction. Chicago, IL 60630is a general contractor providing complete commercial construction and construction…

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CDL-A Truck Driver - Temp-Controlled Freight - up to $1,650/week

Company: Roehl Transport

Location: Chicago, IL

Posted Aug 11, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,365/week. *Home weekly* – typically for 48 hours.

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paid time off relocation assistance sign-on bonus

Dermatology | See 40+ Patients Immediately | $200K Sign-On | Iowa or Illinois

Company: Jackson Physician Search

Location: Illinois

Posted Aug 10, 2025

View Details Apply on healthecareers.com

CDL A Dry Van Truck Driver: Home Weekly

Company: Roehl Transport

Location: Chicago, IL

Posted Aug 11, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,330/week. *Home weekly* – typically for 48 hours.

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malpractice insurance paid time off relocation assistance

Surgery - Minimally Invasive Surgery - Chief

Company: Trinity Health

Location: Maywood, Illinois

Posted Aug 10, 2025

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Program Manager, Data Centers

Company: JLL

Location: Chicago, IL

Posted Aug 11, 2025

Working collaboratively with various stakeholders, you'll ensure successful program execution while proactively addressing risks and driving operational…

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CDL A Truck Driver (Dry Van Freight)

Company: Roehl Transport

Location: Chicago, IL

Posted Aug 11, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,330/week. *Home weekly* – typically for 48 hours.

View Details Apply on SimplyHired
sign-on bonus relocation assistance loan repayment program

Physician Owned, $700K, 6 Weeks Off, Flexible Schedule, Sign-on, Loan Assistance

Company: Duly Health and Care

Location: Quincy, Illinois

Posted Aug 11, 2025

View Details Apply on healthecareers.com
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Program Director (Physician) – Department of Family Medicine Residency

Company: Endeavor Health

Location: Evanston, Illinois

Posted Aug 10, 2025

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403(b) 457(b) wellness program

Nurse Practitioner, Psychiatry/Behavioral Health

Company: SSM Health

Location: Centralia, Illinois

Posted Aug 10, 2025

View Details Apply on healthecareers.com
sign-on bonus relocation assistance loan repayment program

Hem/Onc, $1 Million+, $50K Sign-on, 6 Weeks PTO, Flex Schedule

Company: Duly Health and Care

Location: Quincy, Illinois

Posted Aug 11, 2025

View Details Apply on healthecareers.com

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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