Medicare Advantage

Sorting Chesapeake's 2027 Medicare Menu: Guide

People in Chesapeake can choose from 70 Medicare Advantage plans for 2027, against 67 this year. Three of this year’s plans are gone, 6 are new to Chesapeake city, and 45 that continue have changed their premium, deductible, plan type or name, 16 of them under a new name.

How many Medicare Advantage plans are available in Chesapeake city for 2027, and how to narrow the list to a good fit.

CHESAPEAKE, Va. — If you're turning 65 soon or rethinking your coverage for 2027, here's the honest truth about shopping for Medicare in Chesapeake: there are a lot of choices on the table, and that can feel overwhelming before it feels helpful. Chesapeake sits in Chesapeake city, where 54 Medicare Advantage plans are available for 2027, offered by 6 carriers. Knowing what those numbers mean — and what they don't — is the first step to making a confident pick.

What "67 plans" actually means

Medicare Advantage plans are offered county by county, and Chesapeake city is treated as its own county in Virginia. So when we say 54 plans are available, we mean 54 Medicare Advantage options a Chesapeake resident could consider for 2027, based on CMS's Medicare Advantage and Part D Landscape data.

That doesn't mean you should try to compare all 67. Most people find that once they filter by the doctors they want to keep, the prescriptions they take, and the type of plan they prefer (HMO, PPO, or a Special Needs Plan if they qualify), the realistic list is much shorter.

Also worth knowing: CMS lists 0 stand-alone Part D drug plans as newly available in the city's data slice for 2027 in the way Advantage plans are counted, but stand-alone Part D plans are sold on a broader regional basis. If you stay with Original Medicare, you can still get a stand-alone Part D plan — you'll just shop for it on medicare.gov's Plan Finder using your ZIP code.

How to narrow 67 plans down to a few

A useful order of operations:

1. Start with your doctors and hospitals. If a plan's network doesn't include the providers you use, nothing else about it matters. 2. Add your prescriptions. Plug your exact drugs and doses into medicare.gov's Plan Finder. Formularies vary a lot. 3. Think about how you like to get care. Do you want a referral-based HMO, or the flexibility of a PPO? Do you travel often? 4. Then — and only then — compare costs. Premiums, deductibles, and out-of-pocket maximums matter, but only among plans that already pass steps 1–3.

With about 36,797 residents age 65 and older in Chesapeake, there's a good chance a neighbor, a pharmacist, or a local SHIP counselor has already walked this path.

The 2027 rules that apply everywhere

Some Medicare facts don't change based on where you live. For 2027:

• The Part D out-of-pocket cap is $2,400 in 2027 (it is $2,100 in 2026). Once your drug spending hits that ceiling, you pay nothing for covered drugs the rest of the year.
• The Part D deductible can be no higher than $700 in 2027.
• The old "donut hole" coverage gap is gone as of 2025. Part D now has three phases instead of four.
• The Medicare Prescription Payment Plan lets you spread your drug costs across the year in monthly payments instead of paying at the pharmacy counter. It's optional and free to join.
• IRMAA — the income-based surcharge on Part B and Part D premiums — starts above $109,000 for a single filer in 2026.

Star Ratings and what they signal

CMS publishes Star Ratings (1 to 5) that measure things like customer service, member complaints, and how well plans manage chronic conditions. In the Chesapeake city data for 2027, 0 contracts are rated 4 stars or higher — but ratings shift each year, and a single "contract" can cover many plans across many states, so this number alone isn't a reason to rule anything in or out. Use ratings as one input among several.

Dates to circle

• October 15 – December 7: Medicare Annual Enrollment Period. You can join, switch, or drop a Medicare Advantage or Part D plan. Changes take effect January 1.
• January 1 – March 31: Medicare Advantage Open Enrollment. If you're already in an Advantage plan, you get one chance to switch to another Advantage plan or return to Original Medicare (and pick up a Part D plan).
• If you're new to Medicare, your Initial Enrollment Period is the seven-month window around your 65th birthday month.

Where to get unbiased help

You don't have to figure this out alone, and you don't have to rely on a TV commercial to do it.

• medicare.gov — Use the Plan Finder to compare plans available at your ZIP code with your actual drug list.
• 1-800-MEDICARE (1-800-633-4227) — Available 24/7.
• Virginia Insurance Counseling and Assistance Program (VICAP) — Virginia's SHIP. Free, one-on-one counseling from trained volunteers who don't sell insurance.