Resource library

Medicare and health insurance dates.

The enrollment windows that matter most, in plain language, and a local Chamber member who can help you sort through your options.

Turning 65 or already on Medicare

Medicare dates.

Medicare has set windows for signing up and making changes. Miss one and you may wait months, or pay a penalty for as long as you have coverage.

October 15 to December 7Medicare Open Enrollment. Anyone on Medicare can switch between Original Medicare and Medicare Advantage, change Advantage plans, or join, switch or drop a Part D drug plan. Changes start January 1. Plans change their costs and coverage every year, so it pays to compare.
Around your 65th birthdayYour first chance to sign up. A seven-month window: the three months before the month you turn 65, that month, and the three months after. If you are already getting Social Security, you are usually enrolled in Parts A and B on your own.
January 1 to March 31Medicare Advantage Open Enrollment. If you are in a Medicare Advantage plan, you can switch to a different one or go back to Original Medicare, one time.
January 1 to March 31General Enrollment. For people who missed their first window and do not qualify for a special one. Coverage starts the month after you sign up, and late penalties can apply.
When your situation changesSpecial Enrollment Periods. Moving, losing employer coverage or retiring can open a window outside these dates. Medicare.gov

Self-employed, early retirees and families

Individual health insurance.

If you do not get insurance through work, the Health Insurance Marketplace is where most people buy a plan, often with savings based on income. South Dakota uses HealthCare.gov.

November 1, 2026Open Enrollment starts for 2027 plans. Prices and plans change every year, even if you are happy with yours.
December 15, 2026Sign up by this date for coverage that starts January 1.
January 15, 2027Open Enrollment ends. Sign up by this date for coverage that starts February 1.
Within 60 days of a life eventSpecial Enrollment. Getting married, having a baby, moving or losing other coverage lets you sign up outside Open Enrollment. HealthCare.gov

Plain language

Words to know.

The terms you will hear most when you compare plans.

Medicare

Original Medicare

Part A covers hospital stays. Part B covers doctor visits and outpatient care. You can see any provider that takes Medicare.

Medicare

Medicare Advantage

Also called Part C. A private plan that replaces Original Medicare, often with drug coverage and extras, and usually a provider network.

Medicare

Part D

Prescription drug coverage. Each plan has its own list of covered drugs, so check yours every year.

Medicare

Medicare Supplement

Also called Medigap. Works alongside Original Medicare to help pay the costs it leaves behind, such as deductibles and coinsurance.

Health insurance

Premium, deductible and out-of-pocket max

The premium is what you pay each month. The deductible is what you pay before the plan starts paying. The out-of-pocket max is the most you pay in a year.

Health insurance

Marketplace savings

Based on household income, many people qualify for lower monthly premiums on a HealthCare.gov plan.

Talk to someone local

Local help.

You do not have to sort this out alone. These Chamber members can help you compare your options and answer your questions.

Chamber member

Anderson Insurance – Amber Uphoff

Amber helps people with Medicare and individual health insurance, and she is a local, knowledgeable agent you can sit down with.

Chamber member

Nelson Insurance

Nelson Insurance offers health and life insurance, along with business, home and auto coverage, from its Sioux Falls office.

Looking for home, auto or business insurance? See every insurance agent in the member directory.

This page is general information, not insurance advice. Dates come from Medicare.gov and HealthCare.gov and can change, so confirm with them or with a licensed agent. Last reviewed October 2026.