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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

2023 Annual Report: Focused on You

Chesapeake Employers Insurance's 2023 Annual Report is here. We invite you to take a look and learn how every decision we make is about you – Maryland employers, workers, our agent partners, and our communities.

9/27/2024

Customer Update FAQs: Our Largest Ever Corporate Dividend Announced in 2024!

Approximately 90% of our policyholders will receive a corporate dividend in 2024.

3/1/2024

Chesapeake Employers celebrates the grand opening of its insurance storefront at Junior Achievement of the Eastern Shore

We are grateful for the opportunity to help bring the world of business, insurance, and personal finance alive for local students.

3/1/2024

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

2023 Annual Report: Focused on You

Chesapeake Employers Insurance's 2023 Annual Report is here. We invite you to take a look and learn how every decision we make is about you – Maryland employers, workers, our agent partners, and our communities.

9/27/2024

Customer Update FAQs: Our Largest Ever Corporate Dividend Announced in 2024!

Approximately 90% of our policyholders will receive a corporate dividend in 2024.

3/1/2024

Chesapeake Employers celebrates the grand opening of its insurance storefront at Junior Achievement of the Eastern Shore

We are grateful for the opportunity to help bring the world of business, insurance, and personal finance alive for local students.

3/1/2024

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.

MORE IN THE COMMUNITY