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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

Chesapeake Employers’ Insurance Company Names Mark Isakson as New CEO

The Board of Directors of Chesapeake Employers’ Insurance Company, Maryland’s leading workers’ compensation insurer, announces that Mark Isakson has been named the new CEO, effective April 3, 2023. Mr. Isakson succeeds Thomas Phelan, who announced last fall his intention to retire this year.

2/23/2023

Customer Update – Corporate Dividends Announced for 2023 FAQs

3/1/2022

Ask Your Chesapeake Claims Adjuster About Our New Texting Service

Benefits of the texting service: Provides faster communication and information, translation and interpretation in different languages, and allows you to quickly send links, documents, out-of-work slips, and forms by text.

2/7/2023

Introducing Chesapeake Employers’ Safety Center

Chesapeake Employers’ policyholders now have access to a new service for safety information online: Chesapeake Employers’ Safety Center, powered by Zywave. The learning resources available in Safety Center are a value-added benefit of insuring with us.

9/12/2022

Chesapeake Employers' 2021 Annual Report

In 2021, we were pleased to reward more than 18,000 policyholders with a corporate dividend of $10 million. In total, over the past 4 years, we have paid $40 million in corporate dividends to our qualifying policyholders.

10/6/2022

Featured News & Resources

Chesapeake Employers’ Insurance Company Names Mark Isakson as New CEO

The Board of Directors of Chesapeake Employers’ Insurance Company, Maryland’s leading workers’ compensation insurer, announces that Mark Isakson has been named the new CEO, effective April 3, 2023. Mr. Isakson succeeds Thomas Phelan, who announced last fall his intention to retire this year.

2/23/2023

Customer Update – Corporate Dividends Announced for 2023 FAQs

3/1/2022

Ask Your Chesapeake Claims Adjuster About Our New Texting Service

Benefits of the texting service: Provides faster communication and information, translation and interpretation in different languages, and allows you to quickly send links, documents, out-of-work slips, and forms by text.

2/7/2023

Introducing Chesapeake Employers’ Safety Center

Chesapeake Employers’ policyholders now have access to a new service for safety information online: Chesapeake Employers’ Safety Center, powered by Zywave. The learning resources available in Safety Center are a value-added benefit of insuring with us.

9/12/2022

Chesapeake Employers' 2021 Annual Report

In 2021, we were pleased to reward more than 18,000 policyholders with a corporate dividend of $10 million. In total, over the past 4 years, we have paid $40 million in corporate dividends to our qualifying policyholders.

10/6/2022
In the Community

Chesapeake Employers is proud to be a founding sponsor of and key contributor to Kids’ Chance of Maryland.

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.

Chesapeake's employees are proud to volunteer their time and lend a helping hand to those in need at The Franciscan Center.

MORE IN THE COMMUNITY