Medicare Advantage
Chesapeake Has 67 Medicare Plans: How to Narrow Them
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.
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Key takeaways
- The Annual Enrollment Period runs Oct. 15 – Dec. 7, 2026, and any change you make takes effect Jan. 1, 2027.
- Your Annual Notice of Change (ANOC) is the single most important document to read; it lists what your 2027 plan will cover, charge and include.
- Chesapeake is in Chesapeake city, where CMS lists 67 Medicare Advantage plans from 6 carriers for 2026 — more than enough options to make a side-by-side comparison worth doing.
- Confirmed 2027 Part D figures: a $2,400 out-of-pocket cap and a $700 maximum deductible; the 2027 Part B premium and IRMAA brackets are expected from CMS later this fall.
| Fact | Figure | Source |
|---|---|---|
| Medicare Advantage plans offered in Chesapeake city (2026) | 67 | CMS |
| Medicare Advantage plans offered in Chesapeake city (2027) | 70 | CMS |
| Plans not returning for 2027 / new for 2027 | 3 / 6 | CMS |
| Organizations offering Medicare Advantage in Chesapeake city (2026) | 6 | CMS |
| Share of eligible beneficiaries in Medicare Advantage, Chesapeake city | 40% | CMS |
| Residents age 65 and older, Chesapeake city | 36,797 | U.S. Census Bureau |
| Part B standard monthly premium (2026) | $202.90 | Medicare.gov |
| Part D out-of-pocket cap (2026) | $2,100 | CMS |
| Part D out-of-pocket cap (2027) | $2,400 | CMS |
| Annual Enrollment Period (for 2027 coverage) | October 15 – December 7, 2026 | Medicare.gov |
| Medicare Advantage Open Enrollment Period | January 1 – March 31 | Medicare.gov |
Area counts are for the county as a whole and are not a recommendation of any plan. Program figures are set nationally.
CHESAPEAKE, Va. — It is fall 2026, which means the mail carrier is bringing something important to Medicare households across South Hampton Roads: the Annual Notice of Change, or ANOC, from every Medicare Advantage and Part D plan. That booklet spells out what your plan will look like in 2027 — and the window to act on it closes Dec. 7, 2026.
If you do nothing, your current plan simply renews on Jan. 1, 2027 (assuming it is offered next year), with whatever changes the ANOC describes. That can be fine. It can also mean a new deductible, a different pharmacy tier, or a doctor who is no longer in network. The point of this checklist is to help you find out before the deadline, not after.
What is the Dec. 7, 2026 Medicare deadline for Chesapeake residents?
Dec. 7, 2026 is the last day of the Annual Enrollment Period for 2027 coverage. Any Medicare Advantage or Part D choice you make between Oct. 15 and Dec. 7, 2026 takes effect Jan. 1, 2027.
After Dec. 7, your options narrow. People already enrolled in a Medicare Advantage plan get one more chance — the Medicare Advantage Open Enrollment Period, Jan. 1 – March 31, 2027 — to switch Advantage plans once or move back to Original Medicare. Outside those windows, you generally need a Special Enrollment Period to make changes.
How do I read my Annual Notice of Change (ANOC) for 2027?
Start by comparing your 2027 ANOC side-by-side with your current 2026 Evidence of Coverage. The ANOC's job is to flag what is different; the Evidence of Coverage is the full rulebook.
A few lines to look at carefully:
- The monthly premium and the medical deductible for 2027.
- Primary care, specialist and urgent care copays.
- The maximum out-of-pocket for in-network care.
- The drug deductible, the formulary tiers, and any changes to preferred pharmacies.
- Extra benefits (dental, vision, hearing, over-the-counter, fitness) — these change often from year to year.
If a change jumps out at you, that is your signal to compare other plans before Dec. 7.
How do I check that my doctors, hospitals and prescriptions are still covered in 2027?
Check three directories, in this order: your plan's 2027 provider directory, its 2027 pharmacy directory, and its 2027 drug formulary. All three live on the plan's website and update for the new plan year in the fall.
For Chesapeake residents, that typically means confirming your primary care doctor and specialists, your preferred hospital (Chesapeake Regional, the Sentara hospitals, Bon Secours Maryview and others in the region), and the pharmacy you actually use. Networks can shift from one year to the next even if your plan name stays the same.
For prescriptions, list every drug by name, dose and quantity, then look each one up in the 2027 formulary. Note the tier, any step therapy or prior authorization, and whether a 90-day supply or mail order is preferred. Even a jump of one tier can change what you pay.
The quickest way to compare across plans at once is the Medicare Plan Finder at medicare.gov — you can enter your drug list and preferred pharmacy and see how 2027 plans handle them.
How many Medicare Advantage plans and carriers can Chesapeake residents choose from?
Chesapeake is in Chesapeake city, where CMS's 2026 Landscape Source File lists 67 Medicare Advantage plans from 6 carriers. The 2027 lineup is in the same Plan Finder tool, published for the Oct. 15 start of enrollment.
By plan type, the 2026 roster breaks down as 19 HMO plans, 19 HMO-POS plans, 27 PPO plans and 2 PFFS plans. Twenty-seven are Special Needs Plans (for people with Medicaid, certain chronic conditions, or who live in an institution), and 58 include Part D drug coverage.
The six carriers serving the county are Aetna (CVS Health), Elevance Health (Anthem), Humana, Lifeworks Advantage, Sentara Medicare and UnitedHealthcare. The table below lists every plan by carrier.
What 2027 Medicare figures are already confirmed, and what is still coming?
CMS has confirmed a few 2027 numbers you can rely on while you compare plans. The Part D out-of-pocket cap rises to $2,400 in 2027 (up from $2,100 in 2026), and the Part D maximum deductible rises to $700 (up from $615 in 2026). The Part D national base beneficiary premium for 2027 is $41.33, which is a formula input, not a figure any specific plan charges you.
A few other numbers are not out yet. The 2027 Part B standard premium and deductible, and the 2027 IRMAA income brackets, are typically announced by CMS in November. Watch medicare.gov for those — and ignore anyone trying to quote them as settled before the official release.
Two 2026 program features worth remembering as you shop: the coverage gap ("donut hole") is gone (Part D has three phases now, not four), and the Medicare Prescription Payment Plan lets you spread drug costs across the calendar year in monthly installments at no extra charge.
Where should Chesapeake residents go for personalized Medicare help?
Go straight to the official sources. Medicare.gov has the Plan Finder, your current enrollment, and plain-language explanations; 1-800-MEDICARE (1-800-633-4227) is open 24 hours a day, seven days a week, and can answer questions specific to your situation.
If you have questions about Part B premiums or IRMAA based on your income, the Social Security Administration (ssa.gov or 1-800-772-1213) is the right stop.
By the numbers
Medicare Part B premium, 2006–2026
The standard monthly Part B premium has climbed from $88.50 in 2006 to $202.90 in 2026. Hover any point for that year’s premium.
Source: CMS. Standard premium shown; in some hold-harmless years many existing enrollees paid less. Confirm at Medicare.gov.
By the numbers
How people get Medicare in Chesapeake city
(MA penetration in Chesapeake city)
MA penetration from CMS enrollment data; Medigap share is an estimate. U.S. average is about 54% Medicare Advantage. These are area-level figures, not plan-specific.
The choices, by type
How the Medicare Advantage choices in Chesapeake break down for 2026
Carriers offering plans in Chesapeake city, alphabetically, with the number of plans each offers:
- Aetna (CVS Health) 6 plans
- Elevance Health (Anthem) 13 plans
- Humana 30 plans
- Lifeworks Advantage 2 plans
- Sentara Medicare 2 plans
- UnitedHealthcare 14 plans
HMO plans use a network and usually a primary-care doctor; HMO-POS plans add some out-of-network coverage; PPO plans cover out-of-network care at a higher share; PFFS plans pay any provider that accepts the plan’s terms; Special Needs Plans serve people who are dual-eligible (D-SNP), have certain conditions (C-SNP) or live in an institution (I-SNP). Source: CMS Landscape Source File. No plan is ranked or recommended here.
Key dates
Medicare enrollment periods at a glance
- Around your 65thInitial Enrollment PeriodA 7-month window around the month you turn 65 — your first chance to sign up.
- October 15 – December 7Annual Enrollment Period (Open Enrollment)Anyone with Medicare can join, switch, or drop a Medicare Advantage or Part D plan.
- January 1 – March 31Medicare Advantage Open EnrollmentIf you're already in a Medicare Advantage plan, you can make one change.
- January 1 – March 31General Enrollment PeriodFor people who missed their first chance to sign up for Part B.
- VariesSpecial Enrollment PeriodTriggered by life events like moving or losing other coverage.
Dates are set by Medicare and apply nationwide. Confirm your personal windows at Medicare.gov or 1-800-MEDICARE.
Explore
When can you enroll? An interactive year
Enrollment windows are federal and the same nationwide. Confirm your personal dates at Medicare.gov or 1-800-MEDICARE.
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The parts of Medicare
Good to know
Frequently asked questions
What happens if I do nothing by Dec. 7, 2026?
I missed the Dec. 7 deadline. Can I still change my Medicare Advantage plan?
Do I have to switch plans every year?
Where can I compare 2027 plans available in Chesapeake?
Watch
The Medicare Advantage changes for 2027 in every state, in 30 seconds
- CMS — Medicare enrollment periods (medicare.gov)
- CMS — MA Landscape Source File (plan-level availability by county)
For personalized answers, contact Medicare.gov or 1-800-MEDICARE.
Also for Chesapeake
Sources and methodology
- CMS, Medicare Advantage and Part D Landscape Source Files
- CMS, Medicare Advantage state/county penetration and enrollment files
- U.S. Census Bureau, American Community Survey (table B01001, age 65 and older)
- Medicare.gov, Medicare costs (Part B premium)
- CMS, Medicare prescription drug coverage (Part D) program rules
- CMS, Medicare Advantage and Part D plan-year announcements
- Medicare.gov, enrollment periods and plan rules
Figures cited in this article
- CMS Medicare Advantage Landscape Source File (plan year 2026): the plan and carrier counts for Chesapeake city.
- Medicare.gov: the Annual Enrollment dates, the Medicare Advantage Open Enrollment Period, and the Plan Finder tool.
- CMS 2027 Part D parameter announcement: the $2,400 out-of-pocket cap, $700 maximum deductible and $41.33 national base beneficiary premium.
- Social Security Administration: IRMAA determinations and how income affects Part B and Part D premiums.
How we put this together: area counts come from the CMS files listed above for the county that contains this city, program figures come from CMS, Medicare.gov and the Social Security Administration, and no plan is ranked or recommended.
By The Medicare Desk · Published . For personalized answers, contact Medicare.gov or 1-800-MEDICARE.
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This page was last updated: October 2026.