Health insurance & Medicare · Milwaukee, WI (Milwaukee County)
Medicare Advantage, Supplement & Part D Plans in Milwaukee, Wisconsin
12.2% of Milwaukee residents are 65 or older, about 69,500 people, well below the U.S. average of 17.7%; that is the 2nd-lowest share of residents 65 and older of the 10 Midwest U.S. communities on this site. Side-by-side help with Medicare Advantage, Medicare Supplement (Medigap) and Part D prescription drug plans, whether you are turning 65, retiring from an employer plan, or reviewing your plan during the Annual Enrollment Period. Olive, a licensed agent with Manna Financial Services, helps Milwaukee, WI households compare Medicare plans by phone or video, and the first conversation is free.
What matters for Medicare plans in Milwaukee
Milwaukee is younger than U.S. overall (median age 32.4). Whether you are turning 65 yourself or helping a parent, the seven-month Initial Enrollment Period around the 65th birthday is the window to plan for.
Milwaukee by the numbers
- 12.2% of Milwaukee residents are 65 or older, about 69,500 people, well below the U.S. average of 17.7%; that is the 2nd-lowest share of residents 65 and older of the 10 Midwest U.S. communities on this site.
- 4.1% of adults in Milwaukee are veterans, below the U.S. share of 6.1%.
- About 61,500 Milwaukee residents are between 55 and 64, the group that will reach Medicare age over the next ten years.
- 11.7% of Milwaukee workers have government jobs, below the U.S. share of 14.1%.
Milwaukee and nearby communities
| Place | 65 or older | Median age | Veterans |
|---|---|---|---|
| Milwaukee | 12.2% | 32.4 | 4.1% |
| Chicago | 14.1% | 35.8 | 2.9% |
| Indianapolis | 13.5% | 34.7 | 5.5% |
| Detroit | 15.1% | 35.2 | 4.6% |
| U.S. | 17.7% | 39.1 | 6.1% |
Sources: U.S. Census Bureau, American Community Survey 2019–2023 5-year estimates.
How we help with Medicare plans
- Turning 65: timing for Parts A, B and D to avoid late-enrollment penalties
- Medicare Advantage vs Medicare Supplement, explained side by side
- Prescription check against each plan's drug list
- Annual review during the October 15 to December 7 enrollment period
Rules that apply in Wisconsin
- Your Initial Enrollment Period is the seven months around your 65th birthday: three months before, your birthday month and three months after.
- The Medicare Annual Enrollment Period runs October 15 to December 7 for coverage that starts January 1.
- Medicare Supplement open enrollment lasts six months, starting the month you are 65 or older and enrolled in Part B. During it, insurers cannot turn you down for health reasons.
- For free, unbiased counseling, residents can contact their local State Health Insurance Assistance Program (SHIP) or call 1-800-MEDICARE.
We do not offer every plan available in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options.
Manna Financial Services is not connected with or endorsed by the U.S. government or the federal Medicare program.
Questions from Milwaukee
When can I change my Medicare plan?
During the Annual Enrollment Period, October 15 to December 7, for coverage starting January 1. If you are in a Medicare Advantage plan, the Medicare Advantage Open Enrollment Period from January 1 to March 31 allows one change. Some life events create Special Enrollment Periods.
Do I need to visit an office in Milwaukee?
No. Olive works with Milwaukee and Milwaukee County households by phone or video, so you can compare options from home. Most applications and signatures can be completed online.
Medicare Advantage, Supplement & Part D Plans near Milwaukee
Talk with Olive about Medicare plans.
Free, no obligation, by phone or video. Or call or text (937) 388-5346.