Department of Employee Relations
2027 City of Milwaukee Open Enrollment Kicks Off October 19!
The 2027 Open Enrollment period starts on Monday, October 19, and ends on Friday, October 30! This is the only time, outside a qualifying event, that employees can enroll in or make changes to their 2027 benefits.
For more information or assistance in choosing a plan, please visit the City’s Employee Resource Center website, which includes videos, benefit guides, and more.
About the Employee Resource Center:
- Employees should specify if they are a General City employee, a Sworn Fire employee, or a Sworn Police employee, and indicate the plan year.
- You will have the option to answer questions and upload information about other health plans outside of the City that may be available to you, such as coverage through a spouse’s employer.
- Indicate who you plan to cover and provide your zip code.
- Answer a few short questions about your anticipated usage of the health plan.
How to Enroll In or Make Changes to 2027 Benefits:
- Use the City’s self-service system
- Meet with a Benefit Counselor in person at locations around the City or via a phone appointment.
- The only way to enroll in or make changes to the voluntary benefits (Critical Illness, Accident, and/or Short-Term Disability) is through the Benefit Counselors.
- Call DER Benefits at 414-286-3184
- View Active Rate Charts
What to Know:
- All 2026 elections will carry over except FSA.
- To keep FSA, you must re-enroll for 2027
- Pre-Tax Only for Health & Dental
- As of 2026, after-tax options for health and dental coverage are no longer available.
- There will be rate increases:
- Health 6%
- Delta Dental 4%
- CarePlus Dental 5%
- MetLife Vision 5%
- While the percentage is high, the actual monthly dollar increase is minimal for most plans.
Need Help Choosing a Plan?
We’re excited to launch a new decision support tool on the Employee Resource Center. This tool helps you compare plans and make informed choices based on your personal needs. Visit the Employee Resource Center.
Open Enrollment Webinars
The DER Benefits Team will host five enrollment fairs across multiple City locations.
- Wednesday, October 21
- 10:00 a.m. - 1:00 p.m.
- City Hall Rotunda, 200 E. Wells Street
- *Special event*
- 10:00 a.m. - 1:00 p.m.
- Thursday, October 22
- 2:00 p.m. - 4:30 p.m.
- DPW Field Headquarters Cafeteria, 3850 N. 35th St.
- 2:00 p.m. - 4:30 p.m.
- Friday, October 23
- 12:00 p.m. - 1:00 p.m.
- VIRTUAL - link to follow
- 12:00 p.m. - 1:00 p.m.
- Monday, October 26
- 2:00 p.m. - 4:30 p.m.
- DPW Field Headquarters Cafeteria, 3850 N. 35th St.
- 2:00 p.m. - 4:30 p.m.
- Tuesday, October 27
- 2:00 p.m. - 5:00 p.m.
- DNS Lake Tower, 4001 S. 6th Street
- 2:00 p.m. - 5:00 p.m.
- Thursday, October 29
- 2:00 p.m. - 5:00 p.m.
- Fire and Police Academy, 6680 N. Teutonia Ave.
- 2:00 p.m. - 5:00 p.m.
Plans with Deduction Frequency Changes
| Plan | Current Frequency | Updated Frequency as of Jan 1, 2026 |
| Vision | 1st paycheck each month |
1st and 2nd paycheck each month |
| Flexible Spending | 1st and 2nd paycheck each month |
Every check |
| Long Term Disability | Every check | 1st and 2nd paycheck each month |
| Accident Insurance | Every check | 1st and 2nd paycheck each month |
| Critical Illness | Every check | 1st and 2nd paycheck each month |
| Short Term Disability | Every check | 1st and 2nd paycheck each month |
| Voluntary Life Insurance | 2nd paycheck each month |
1st and 2nd paycheck each month |
| Health Appraisal Fee | 2nd paycheck each month |
1st and 2nd paycheck each month |
| Commuter Value Pass | 1st paycheck each month |
1st and 2nd paycheck each month |
Plans with No Deduction Frequency Changes
| Plan | Current Frequency |
| Health Plan | 1st and 2nd paycheck each month |
| Dental Plan | 1st and 2nd paycheck each month |
| Deferred Compensation | Every check |
| Pension | Every check |

