Medicare

Explore health insurance and prescription plans to find the right coverage for you.

We’ll help you find a plan that fits
your needs.

  • Online

    Get free advice and compare
    plans with a licensed insurance
    agent at Allstate Health Solutions*
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  • Phone

    Speak with a licensed insurance
    agent at
    Allstate Health Solutions*†
    Mon – Fri 8 am – 9 pm EST
    Sat and Sun closed
  • In person

    Speak with a licensed insurance agent from Sidebar Benefit Advisors at a local Walgreens‡
Find an agent near youOpens a simulated dialog

Don't miss the 2027 Medicare Open Enrollment Period, Oct. 15 - Dec. 7, 2026!

Ready to enroll? Here’s what you need

Have the following information ready to help simplify the enrollment process.

  1. Your ZIP code
  2. List of your current healthcare providers
  3. List of your medical conditions
  4. List of medications you take
  5. Your Medicare card (if you’ve enrolled before)
  6. Photo ID (bring to in-person consultations)

5 important questions to consider

  1. Does my plan have a preferred pharmacy network?
  2. Where are my current medications on the plan's formulary?
  3. Should I consider a Prescription Drug Plan (PDP) or a Medicare Advantage Prescription Drug Plan (MAPD)?
  4. What will be the total monthly cost?
  5. Do I qualify for financial assistance such as Extra Help or low-income subsidies?

Need help reviewing your Medicare coverage options?

Get free support online or in person, with no obligation to enroll.

Get support online or by phone

Compare & review Medicare coverage
options with a licensed
Allstate Health Solutions agent
from the comfort of home

Get startedopens a simulated dialog

Get support in person

Compare & review Medicare coverage
options with a licensed
Sidebar Benefit Advisors agent
at your local Walgreens

Get startedopens a simulated dialog

Watch the video below to learn how to enroll in Medicare.

* No obligation to enroll. This ad is not from the government. It’s from Allstate Health Solutions, an insurance agency selling plans from many insurance companies. We do not offer every plan available in your area. Currently we represent 21 organizations which offer 52, 101 products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options. The Medicare plans represented are PDP, HMO, PPO or PFFS plans with a Medicare contract. Enrollment in plans depends on contract renewal. Enrollment in a plan may be limited to certain times of the year unless you qualify for a special election period, or you are in your Medicare Initial Period. Not all plans offer all benefits mentioned. Deductibles copay and coinsurance may apply. Allstate Health Solutions, is a licensed health insurance agency. It does not underwrite or administer health insurance policies. Customers interested in health insurance products will be assisted by a licensed insurance agent from Allstate Health Solutions

‡ MULTIPLAN_HCIAHSWLGRNSWEBPY27_C

† Monday through Friday 8 a.m. to 9 p.m. EST. Allstate Health Solutions is a licensed insurance broker. No commissions are paid to Walgreens.

‡ Advice is free with no obligation to enroll and provided by independent licensed agents representing one or more plans. Licensed agents are not employees or agents of Walgreens,Allstate Health Solutions, or any government agency.

‡ We do not offer every plan available in your area. Currently, we represent multiple organizations which offer Medicare Advantage, Prescription Drug, and Medicare Supplement Insurance plans.

‡ Please contact Medicare.gov, 1-800-MEDICARE (TTY: 1-877-486-2048) to get information on all of your options.

‡ Sidebar Benefit Advisors is not connected with or endorsed by the United States government or the federal Medicare program.

‡ The Medicare plans represented are PDP, HMO, PPO, or PFFS plans with a Medicare contract. Enrollment in plans depends on contract renewal. Enrollment in a plan may be limited to certain times of the year. Eligibility may require a Special or Initial Enrollment Period.

‡ Sidebar Benefit Advisors is a technology platform operated by Ithaca Health, a licensed health insurance agency. The purpose of this site is the solicitation of insurance. Contact may be made by a licensed insurance agent or insurance company.

‡ This is a solicitation for insurance. By requesting information, scheduling a call, or initiating a chat, you agree to be contacted by a licensed insurance agent by phone, email, or text message to discuss Medicare insurance plans. Standard messaging rates may apply.

‡ Sidebar Benefit Advisors is a free service with no obligation to enroll. Your information and use of this site is governed by our Terms of Use and Privacy Policy.

‡ Other pharmacies are available in-network.

‡ Walgreens does not endorse or recommend any specific Medicare plan. Walgreens pharmacy network participation varies by plan. Walgreens® is a registered trademark of Walgreen Co. and is used here for informational purposes only.

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