Official websites use

A website belongs to an official government organization in the City of Boston.


Secure .gov websites use HTTPS

A lock or https:// means you've safely connected to the .gov website. Share sensitive information only on official, secure websites.

Last updated:

Benefits Available to City Workers

Annual enrollment is open for City of Boston workers from May 1 - May 19, 2023. Check out our blog post to get more information to help you determine whether you need to take action.

Find out what benefits you have as a City of Boston worker. We have a list of our current programs below. Learn about the many benefits you can enjoy as a City of Boston employee. 

For health insurance questions, contact:

Health Benefits Office
1 City Hall Square, Room 807
Boston, MA 02201

Email: | Phone: 617-635-4570
Fax: 617-635-3932
Office hours: Monday through Friday, 9 a.m. - 5 p.m.

Insurance Benefits

Group Health Insurance

We have three health insurance plans for City of Boston employees (excluding seasonal and emergency hires) who work at least 20 or more hours a week on a regular basis.  


Group Life Insurance

You must enroll in basic life insurance if you wish to enroll in a City health insurance plan. The basic life insurance is a $5,000 group term policy. Some unions may be eligible to elect the $10,000 benefit. The cost for this benefit is shared 50/50 between the City and employee. If you enroll in basic life insurance and want additional coverage, you can also enroll in the optional life insurance policy for an amount up to your base salary (maximum amount is $74,000). The cost is based on the amount of coverage and your age, and is 100 percent employee paid.


For a more comprehensive review of the City of Boston's health benefits offerings for employees, read the new hire benefits guide.


The program covers employees after they stop working with the City of Boston. You can keep your insurance for up to 18 months. You will have to pay your total monthly premium plus a 2 percent administrative fee. Read more information about COBRA.

Medicare (retiree) group health insurance

As a retiree of the City of Boston, you are eligible to continue your health coverage. By law, all Medicare-eligible retirees, spouses, and dependents must apply for Medicare Parts A & B and switch to a Medicare plan to continue coverage. We offer six Medicare plans to supplement Medicare Parts A & B for our retirees. Visit the benefits available to retirees page for more information.

Dental and vision

Massachusetts Public Employee Fund

If you qualify, you’ll get an enrollment form after six months of working for the City. You'll have the choice between an indemnity plan or a network plan. You'll also be able to sign up for individual benefits or a family plan.

There’s an informational booklet about the Massachusetts Public Employee Fund. You can also find out which unions get coverage through the fund. For more information, visit the Massachusetts Public Employee Fund website, or contact them at:

NOT IN THE Public employee FUND?

Other workers at the City can get dental and vision insurance through their unions. There are several unions that offer this benefit, including:

Coverage through your healthcare plan

You could save money by getting your dental insurance through your healthcare provider. Make sure to go over your coverage summary to see what they have to offer.

Most healthcare plans will cover regular vision exams. Some plans offer discounts on eyeglasses and contact lenses at certain stores. Check with your health insurance carrier for details:

Work and life benefits

voluntary insurance

Other insurance providers offer short and long-term disability. They also offer optional life insurance and critical illness coverage. Please be advised that these benefits are not administered by the Health Benefits Office.

MBTA Pass Program

You can purchase an MBTA pass and have the cost deducted from your payroll before taxes. Public School employees who work at 26 Court St. can buy Charlie Cards through the same program.

Child Care

We offer child care services for children from three months to seven years old. Services are offered through our City Hall Child Care Program.

Employee Assistance Program

The free and confidential program for workers and their families focuses on wellness through assessments, referrals, treatment, and other services.

Paid Time Off

We offer paid time off based on your position and years of service at the City.

Sick Leave Redemption

You can redeem unused sick days for a lump sum of cash. You can only redeem them if you've used less than five sick days in the last year, ending on December 31.

Sick Leave Pools

Employees in certain roles can donate sick days into a pool on a yearly basis.

Paid Holidays

We offer generous Holiday benefits and paid holidays to all full-time employees.

Leave of Absence

We have a number of leave programs, depending on situation. These programs can be paid or unpaid.

Tuition Reimbursement

Employees in the AFSCME, SEIU, SENA unions can get money for school. We reimburse you for the cost of education that’s related to your work.

Savings and investment benefits

Flexible spending accounts

Flex Spending lets you deduct pre­-tax money for out-of-pocket medical expenses, dependent care, and transportation. Annual Enrollment for Flex Spending occurs in November for the plan year beginning January 1. Participants of this program will receive a Benny Card at the start of the new year that they can begin using immediately for eligible expenses.

Retirement Planning

We offer three types of retirement planning programs:

City of Boston Credit Union

City workers are welcome to join the City of Boston Credit Union. The credit union offers competitive interest rates, club discounts, and other benefits.

Direct Deposit

You can deposit your paycheck right into your bank account.

Benefits billing

If you receive a benefits billing statement related to your City of Boston health or life insurance, you have two options to pay for the coverage: 

Make a check out to 'City of Boston':

Attn: Health Benefits and Insurance
Room 807
Boston, MA 02201

Pay online
  • Visit our payment website. Please refer to your Benefits Billing Statement. Complete the requested information to submit your payment online.
  • Payments made by electronic check / ACH are not subject to a service charge. The online credit card service charge is 2.75 percent of the total payment ($1 minimum). 
  • Upon receipt of your payment, it will be processed and posted to your account within two to four business days.

NOTE: If you are receiving an active paycheck or pension, your deductions will not be affected.

Back to top