Medicare Choices

The most reliable source for information about Medicare is the agency’s own website,  www.medicare.gov/ . It’s menus and search tool make it easy to navigate and find the information you need. Below are direct links to some of the most useful parts of the website, along with a few other selected sources.

Where to get personalized help with your Medicare-related questions

If you need personalized help such as understanding & comparing your options or other health insurance questions, your state SHIP program should be the first place you call.

Before talking to an insurance agent or broker, learn about them and how they are paid in these articles from Fortune.com and MedPageToday.

Medicare.gov – Tools for Making Decisions

Start here for most questions about Medicare:

getting started w Medicare

You can also jump directly to decision-making tools for specific questions.

Am I eligible for Medicare? How much will I pay?

What if I or my spouse are still working and have insurance through that job? Should I still sign up for Medicare A and B when I turn 65? This fact sheet will walk you through the questions you should ask, and the rules you need to know – both for right now and for later, if you will have retiree insurance or COBRA.

How do I sign up for Medicare?

I didn’t sign up for Medicare when I turned 65. When else can I sign up for Parts A & B?

When can I buy a Medigap (Medicare Supplement) policy?

  • You have a guaranteed issue right (meaning that you can purchase any plan from any company you like, and you cannot be turned down for any reason) during your Medigap Open Enrollment Period – the 6-month period beginning with the first month you have Medicare Part B and you’re 65 or older. See page 14 in the Medicare publication, Choosing A Medigap Policy.
  • There are a few limited situations other than your Medigap Open Enrollment Period where you would have guaranteed issue rights. Most have to do with losing other coverage (Advantage, COBRA, employer, etc.) or when you’ve only been on Advantage for less than a year before switching (back) to Original Medicare. Read the list of situations in the Medicare publication, Choosing A Medigap Policy, p. 22-23.  To double-check, use the tool at https://www.medicare.gov/health-drug-plans/medigap/ready-to-buy/when to walk through a series of questions about your situation.
  • Illinois has two ways that you may be able to choose a new Supplement (Medigap) policy if you did not purchase one initially, or you have one but would like to change.
    • If you did not initially sign up for a Supplement policy, there is one company that will apparently sell anyone over age 65 the same policy at the same price regardless of health condition. See page 12 of the Illinois Medicare Choices book. Download it by clicking on “new 2025 Medicare Choices Guide” here.
    • If you are between the ages of 65 and 75 and you already have a Supplement policy but would like to change it, you may be able to switch to a similar plan or one with a lower benefit from the same company during your New Medicare Supplement Open Enrollment period starting on your birthdate each year. The open enrollment period lasts for 45 days. See page 10 of the Medicare Choices book. Download it by clicking on “new 2025 Medicare Choices Guide” here.

What Advantage, Part D Prescription and Supplement (Medigap) are available in my area? How do their benefits and costs compare?

When can I switch plans, or join a Part D prescription plan or an Advantage Plan for the first time? These aren’t interactive tools, but they list and explain each of the different types of enrollment opportunities and who is eligible for each one.

Medicare Publications

Medicare’s most complete publication is Medicare and You. Revised every year, you’ll receive a hard copy each year unless you opt out. It should be required reading for anyone who is enrolling in Medicare for the first time.

  • Order a hard copy or download a PDF of  Medicare & You at https://www.medicare.gov/publications Scroll down if you don’t see the Medicare & You link.
  • The hard copy will include state-specific info not provided in the PDF version, listing cost details about individual Advantage plans, Part D prescription plans, and Medicaid plans. Neither version includes details about Supplement Plans. But you can view all of that information for all those types of plans with the Compare Plans tool at https://www.medicare.gov/plan-compare/.

Medicare also offers numerous other publications that provide more complete details on specific subjects.

Other Recommended Tools

If you’re a visual person or like using flowcharts to figure things out, you might like this set of tools created by a company called fpPathfinder. That company licenses its tools to financial planners, who in turn can make them available on their websites. For example, you’ll find all five of their Medicare flowcharts at https://retirementplanningeducation.com/more-free-stuff. Scroll down to the Medicare tools. Or use these links to the individual flowcharts: