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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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2027 PLAN ALERT

Medicare Advantage plans in your area are changing or leaving for 2027.

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BEFORE YOU ENROLL

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  • Your doctors — confirmed in-network for 2027
  • Your prescriptions — checked against the plan's 2027 drug tiers
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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.
Before Dec. 7Chesapeake, VA
Video: Kampus Production Video by Kampus Production on Pexels
Key facts: Medicare in Chesapeake, Virginia (data as of 2026-06-01)
FactFigureSource
Medicare Advantage plans offered in Chesapeake city (2026)67CMS
Medicare Advantage plans offered in Chesapeake city (2027)70CMS
Plans not returning for 2027 / new for 20273 / 6CMS
Organizations offering Medicare Advantage in Chesapeake city (2026)6CMS
Share of eligible beneficiaries in Medicare Advantage, Chesapeake city40%CMS
Residents age 65 and older, Chesapeake city36,797U.S. Census Bureau
Part B standard monthly premium (2026)$202.90Medicare.gov
Part D out-of-pocket cap (2026)$2,100CMS
Part D out-of-pocket cap (2027)$2,400CMS
Annual Enrollment Period (for 2027 coverage)October 15 – December 7, 2026Medicare.gov
Medicare Advantage Open Enrollment PeriodJanuary 1 – March 31Medicare.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:

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.

$0$50$100$150$200200820122016202020242026

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

40% are on Medicare Advantage
(MA penetration in Chesapeake city)
40%
60%
Medicare Advantage Medicare Supplement (Medigap) Original Medicare only
U.S. average

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

67
Medicare Advantage plans
6
Carriers offering them
19
HMO plans
19
HMO-POS plans
27
PPO plans
2
PFFS plans
27
Special Needs Plans
58
Include drug coverage

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.

Compare with a licensed agent

See Medicare options serving Chesapeake & speak with a licensed agent

Medicare Advantage companies in Chesapeake city

By local enrollment size · informational, not a ranking
CompanyLocal enrollmentPlans offeredLocal agentsAction
HumanaNational—Yes
Elevance Health (Anthem)National—Yes
UnitedHealthcareNational—Yes
Aetna (CVS Health)National—Yes
Sentara Health Care (shc)Regional—Yes
Sentara Life Care Corporation INCRegional—Yes
Enrollment data: CMS Medicare Advantage enrollment by company (county level). Listed by enrollment size, largest first — this is not a ranking, recommendation, or endorsement of any company or plan.

Provided by licensed insurance partners; MyMedicarePlans.org may be compensated. Not a ranking or endorsement of any plan.

Explore

When can you enroll? An interactive year

JFMAMJJASOND
October 15 – December 7 — anyone with Medicare can join, switch, or drop a Medicare Advantage or Part D plan. Changes take effect January 1.

Enrollment windows are federal and the same nationwide. Confirm your personal dates at Medicare.gov or 1-800-MEDICARE.

Explore

The parts of Medicare

Part A covers inpatient hospital stays, skilled nursing facility care, hospice, and some home health care. Most people pay no premium for Part A.

Good to know

Frequently asked questions

What happens if I do nothing by Dec. 7, 2026?
Your current Medicare Advantage or Part D plan renews on Jan. 1, 2027, with the changes described in your Annual Notice of Change — as long as the plan is still offered. If your plan is being discontinued, your ANOC will say so, and you will have a Special Enrollment Period to pick a new one.
I missed the Dec. 7 deadline. Can I still change my Medicare Advantage plan?
If you are already in a Medicare Advantage plan, the Medicare Advantage Open Enrollment Period, Jan. 1 – March 31, 2027, lets you switch to a different Advantage plan once or return to Original Medicare (and add a stand-alone Part D plan). Other changes typically require a Special Enrollment Period.
Do I have to switch plans every year?
No. Many people keep the same plan for years. The reason to review every fall is simple: plan details, drug formularies and provider networks can change, and so can your own health and prescriptions. A 20-minute check against the ANOC is how you catch a mismatch before January.
Where can I compare 2027 plans available in Chesapeake?
The Medicare Plan Finder at medicare.gov lets you enter your ZIP code, prescriptions and preferred pharmacy, then compare every 2027 Medicare Advantage and Part D plan offered in Chesapeake city side by side. You can also call 1-800-MEDICARE for help walking through it.

Watch

The Medicare Advantage changes for 2027 in every state, in 30 seconds

Sources & further reading
  • 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

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.

Content Integrity Standards

  • No invented figures. Program-level numbers come from CMS / Medicare.gov; we never use placeholder data.
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This page was last updated: October 2026.

Medicare plans in your area changing for 2027 — check yoursCall