An Independent Medicare Health Insurance Agency

Sign Up For Medicare in Winchester, IN

Hi, I’m Niki! My team of Winchester-based Medicare insurance agents are here to help! We personalize Medicare Supplement, Medicare Advantage and Medicare Prescription Drug Plan choices for people on Medicare in Randolph County! Make an online Zoom appointment today!

Winchester, Indiana Medicare insurance.

Let’s Discuss Your Medicare Options!

Our Winchester, IN Medicare agents customize your insurance

Sign up for Medicare in Winchester and let Chicagoland Medicare be your trusted insurance agent. With our expertise, we can guide you through the process of choosing the right Medicare plan in Winchester. Did you know that Winchester is home to the Historic Union City (HUC) Railroad Depot? It's one of the oldest train depots in the state and has been restored to its original condition. Contact Chicagoland Medicare today and let us make your Medicare enrollment experience a breeze in Winchester! Fun fact: Winchester is known as the "Cradle of the Fireless Steam Engine," as it was the birthplace of the Geiser Manufacturing Company, one of the leading producers of fireless steam engines in the early 20th century.

Schedule a Zoom meeting with a Chicagoland Medicare expert to compare 2025 Randolph County Medicare insurance plans from Aetna, Blue Cross and Blue Shield, Humana and UnitedHealthcare (UHC).

Chicagoland Medicare local licensed agents in Winchester sell Medicare Advantage, Medicare Supplement, Medigap and Medicare Part D Prescription Drug Plans (PDP) as well as Medicare dental, vision and hearing insurance policies. If you have additional questions about your plan rates or benefits, schedule an appointment with Niki and her team!

Understanding Medicare Eligibility in Winchester, Indiana

Understanding Medicare Eligibility in Winchester, Indiana

Whether you are still working in Winchester or have retired, becoming eligible for Medicare is a significant milestone. Now is the time to review your benefits and take appropriate action. Read More »

5 Tips for Choosing the Best Medicare Insurance Plan in Winchester, IN

5 Tips for Choosing the Best Medicare Insurance Plan in Winchester, IN

When selecting a Medicare plan in Winchester, it’s important to consider your medical needs and budget. It also helps to review how each plan compares in terms of prescription drug coverage and provider network options. Read More »

What can’t you do during Indiana Medicare Advantage Open Enrollment?

What can’t you do during Indiana Medicare Advantage Open Enrollment?

If you decide to drop your Winchester Medicare Advantage plan and buy a Medicare Part D Prescription Drug plan during OEP, you’ll be bumped off of Medicare Advantage and default back to Original Medicare. Read More »

Let us help you find the right Medicare insurance plan to fit your healthcare needs and budget.

in Winchester, Indiana.

Chicagoland Medicare is a boutique Medicare insurance agency serving Winchester and all of Randolph County. We are NOT a call center. We exclusively use Zoom and are “by appointment only.”

Need help scheduling a zoom call?

At Chicagoland Medicare, we’re local, unique and boutique!

Educate. Customize. Enroll.

Are you a financial planner, caregiver or taking care of your parent's Medicare policies?

We’re happy to accommodate all with kindness, compassion, and efficiency.

We customize Indiana Medicare insurance plans to meet your specific needs.

I’m Niki, the owner of Chicagoland Medicare. Medicare insurance coverage changes every year. We think stability, affordability and predictability are important. That’s why we exclusively offer Medicare Advantage, Medigap, Medicare Supplement, Medicare Part D Prescription Drug Plans and dental, vision and hearing insurance plans from national carriers such as: Aetna Medicare, UnitedHealthcare, Blue Cross and Blue Shield Medicare, Humana Medicare and Mutual of Omaha Medicare.

Your time is valuable. That’s why we use Zoom and other cutting-edge technology to solve your Medicare insurance needs so you can get on with your day!

To sign up for Medicare, you must first sign up for Social Security.

The official Muncie IN Social Security office is the closest full service Social Security office near Winchester, IN.

Muncie IN Social Security Office
600 North Walnut St
Muncie, IN 47305

Phone: 866-964-7586
Fax: 833-902-2682

Still need help?
Contact your local senior health insurance resource in Indiana.

Senior Health Inurance Program
800-452-4800
311 W. Washington Street, Ste 300
Indianapolis, IN 46204