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What Sets Us Apart
Dependable, Reliable & Financially Strong
Competitive Pricing & Value-Added Benefits
Professional Safety Services & Free Safety Resources
Integrated Health & Claims Services
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The Chesapeake Employers' Advantage

We Make Coverage Easy

We can take the confusion out of workers' compensation insurance coverage.

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Get Covered Across the States

Did you know that Chesapeake Employers has teamed up with a national insurer to provide an insurance solution for other states coverage?

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The Chesapeake Difference

More Maryland businesses choose Chesapeake Employers than any other workers' compensation insurance company.

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Keeping Your Premium Low

We work to help you control your premium costs by championing workplace safety along with creating a return-to-work program.

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Featured News & Resources

2024 Annual Report: Elevating Tomorrow with Purpose

Chesapeake Employers Insurance’s 2024 Annual Report is here. We invite you to learn more about our commitment to all Maryland businesses and why it matters so deeply today, tomorrow, and well into the future.

9/18/2025

Chesapeake Employers Insurance Declares $60 Million Policyholder Dividend for 2026

Chesapeake Employers' Insurance Company's Board of Directors declared the company's highest-ever policyholder dividend of $60 million for 2026.

12/23/2025

2027 Board Nominations & Application Process Information

Information regarding the 2027 Board Nominations and Elections will be posted here at a later date.

6/2/2026

Multi-factor Authentication Now Available!

We are activating multi-factor authentication for all eServices users. This security feature will require at least two forms of identification to access your Chesapeake account.

4/1/2024

Now Offering Informative Webinars

FREE to Attend Online - Registration Required. Check out the latest webinars including Landscaping and Arborist Safety, Understanding and Responding to Workplace Violence, Exploring Safety Center, and Defensive Driving Awareness.

5/12/2023

Featured News & Resources

2024 Annual Report: Elevating Tomorrow with Purpose

Chesapeake Employers Insurance’s 2024 Annual Report is here. We invite you to learn more about our commitment to all Maryland businesses and why it matters so deeply today, tomorrow, and well into the future.

9/18/2025

Chesapeake Employers Insurance Declares $60 Million Policyholder Dividend for 2026

Chesapeake Employers' Insurance Company's Board of Directors declared the company's highest-ever policyholder dividend of $60 million for 2026.

12/23/2025

2027 Board Nominations & Application Process Information

Information regarding the 2027 Board Nominations and Elections will be posted here at a later date.

6/2/2026

Multi-factor Authentication Now Available!

We are activating multi-factor authentication for all eServices users. This security feature will require at least two forms of identification to access your Chesapeake account.

4/1/2024

Now Offering Informative Webinars

FREE to Attend Online - Registration Required. Check out the latest webinars including Landscaping and Arborist Safety, Understanding and Responding to Workplace Violence, Exploring Safety Center, and Defensive Driving Awareness.

5/12/2023
In the Community

Chesapeake Employers strives to support local charitable organizations and causes in Maryland.

Chesapeake Employers is proud to help bring the world of business, insurance, and personal finance alive for students at Junior Achievement.

Caring for Marylanders is more than a job for our employees and our organization, it's our passion. Our giving spirit guides all we do, both at work and in the community.

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