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Express Pay

Policy Lookup
Payment Info

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Common Questions

Express Pay is a simple and secure payment service for Chesapeake Employers' customers who want to pay their bills online without signing in or having to create an account. Express Pay accepts payments via Credit Card (Visa, Mastercard, Discover, and American Express), as well as through your checking or savings account by way of an Electronic Funds Transfer (EFT). Please note that Express Pay will not provide detailed billing information.

A Quote Number is an 8-digit number given during your first new business quote with us, as well as any any subsequent quote to renew your policy.

A Policy Number is a 9-digit number used throughout the life of your policy and can be broken down as two separate numbers with the first 7 digits being your policy number and the last 2 digits being the term.

For example, if your policy number is 123456701, the first 7 digits (1234567) are the policy numbers, while the last 2 digits (01) refer to the term of your policy. In this case, 01 would mean this is your first policy term with us. If you renewed your policy for another term, the 01 would then change to 02, since this would then be your second policy term with us.

Yes! Check out our Express Pay Quick Reference Guide for additional help.

Yes, Express Pay can process payments on renewals and new business quotes. Simply input the 8-digit quote number assigned along with the policy effective date.

Payments will be posted to your policy immediately. You will also receive an email confirming that your transaction posted successfully. You can verify your new Current Term Balance Due by reinputting your policy number and effective date on the Express Pay main menu. To view additional transaction details, please log in.

Yes, you can pay partial amounts with different payment methods using the "Pay another amount" option. There is no limit on the number of payments for each type of authorized payment method as long as the payment is at least one dollar ($1.00). Please allow 48-72 hours for EFT payments to be processed through your financial institution. Insufficient funds will incur a $35 fee and the credit to your policy will be reversed.

Express Pay is designed as a "pay now" service, therefore it cannot handle future or recurring payments at this time. 

If you have received a confirmation number for a transaction that you would like to delete or change, our Customer Service department can assist you. Customer Service is available by calling 410-494-2000 or 1-800-264-4943, Monday through Friday from 8:00 a.m. to 5:00 p.m., Eastern Standard Time (EST).

If you have an outstanding balance on a prior policy term, any payments made will be applied to the oldest outstanding balance first. Any remaining balance from your payment will then be applied to your current policy term. To verify if you have a prior policy term balance, please log in or call Customer Service at 410-494-2000 or 1-800-264-4943.  

Yes, if your policy has been canceled you can still make payments on it. However, retroactive reactivation of coverage is contingent upon review and approval by Chesapeake Employers. To verify if your policy is in a canceled status, please log in or call Customer Service at 410-494-2000 or 1-800-264-4943.