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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

Chesapeake Employers Insurance Declares $55 Million Dividend, 8% Rate Decrease

Chesapeake Employers' Insurance Company's Board of Directors declared the company's highest-ever policyholder dividend of $55 million for 2025. Additionally, the company filed an 8% net rate decrease with the Maryland Insurance Administration, effective April 1, 2025

2/27/2025

2025 Board Nominations & Application Process Begins 12/2/24

The nomination and application process to elect two members to Chesapeake Employers' Board of Directors begins December 2, 2024. The election will take place during the Annual Meeting of Policyholders in June 2025. For more information, nominee criteria, and to apply, please visit our Board Nominations & Elections page.

12/3/2024

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

Chesapeake Employers Insurance Declares $55 Million Dividend, 8% Rate Decrease

Chesapeake Employers' Insurance Company's Board of Directors declared the company's highest-ever policyholder dividend of $55 million for 2025. Additionally, the company filed an 8% net rate decrease with the Maryland Insurance Administration, effective April 1, 2025

2/27/2025

2025 Board Nominations & Application Process Begins 12/2/24

The nomination and application process to elect two members to Chesapeake Employers' Board of Directors begins December 2, 2024. The election will take place during the Annual Meeting of Policyholders in June 2025. For more information, nominee criteria, and to apply, please visit our Board Nominations & Elections page.

12/3/2024

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.

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