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2025

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Best Health Insurance Agencies in Chesapeake, VA

Our Recommended Top 5

We did the research for you!

  • Licensing
  • User Reviews
  • Mystery Shopping Calls

Our goal is to connect people with the best local professionals. We scored Chesapeake health insurance agencies on more than 25 variables across five categories, and analyzed the results to give you a hand-picked list of the best.

4423Reviewed

2655Curated

5Top Picks

Learn about our selection process.

Providers

featured provider = Featured Provider

Best Health Insurance Agencies Serving Chesapeake
809 Greenbrier Parkway, Chesapeake, VA 23320
Visit WebsiteLicense: 142671

Expertise.com Rating

Review Sources

Facebook
4.0 (46)
Google
5.0 (1)

Why choose this provider?

Choice Insurance Agency is a Virginia Beach-based company that offers insurance products and services in the Chesapeake metro and surrounding areas. It is a local and independent insurance brokerage firm that caters to businesses and individuals seeking health insurance policies. The company's team of more than 15 insurance professionals helps clients acquire other plans, including life, commercial, coastal, and private client group coverages. George Ayers founded Choice Insurance Agency in 2008 from the former Realty Consultants Insurance Agency.

  • Individual Plans
  • Life Insurance

Best Health Insurance Agencies Serving Chesapeake
3 Commercial Place, Norfolk, VA 23510
Visit WebsiteLicense: 109898

Expertise.com Rating

Review Sources

Google
4.4 (7)

Why choose this provider?

Towne Benefits is an independent insurance agency that represents customers and assists them in finding health insurance plans in Chesapeake and nearby areas. The agency represents a vast network of health insurance carriers that provide coverage for medical, surgical, and hospital expenses, and it provides assistance for clients from filing claims to renewing coverage. Additionally, Towne Benefits helps with Medicare and its agents assist in evaluating senior clients' prescription drugs, finances, health, and long-term healthcare needs.

  • Individual Plans
  • Group Plans

Best Health Insurance Agencies Serving Chesapeake
517 Baylor Court, Chesapeake, VA 23320
Visit WebsiteLicense: 152649

Expertise.com Rating

Review Sources

Google
5.0 (2)

Why choose this provider?

We Insure serves individuals, families, and groups in and around the Chesapeake metro. It offers home, auto, and business protection products from different carriers. The firm provides health coverage options for independent contractors, self-employed, college students, seniors without Medicare, and unemployed individuals. The agency also offers supplemental health insurance in the event of a covered accident or critical illness. These plans work with major medical policies but do not coordinate with other health benefit plans.

  • Life Insurance

Best Health Insurance Agencies Serving Chesapeake
4500 Main Street, Virginia Beach, VA 23462
Visit WebsiteLicense: 558892

Expertise.com Rating

Why choose this provider?

Brown & Brown Insurance provides services to individuals and businesses in Chesapeake and the surrounding communities. It offers various insurance products, including healthcare, fitness, risk management, specialty emergency, and workers' compensation insurance policies. Moreover, it provides automobile, general liability, home, motorcycle, and umbrella insurance plans. Brown & Brown Insurance's services companies in construction, community associations, and real estate industries. Bill Strachan, the firm's president, holds a degree in Business Administration and Finance and has CIC and VBS designations.

  • Individual Plans
  • Life Insurance

Best Health Insurance Agencies Serving Chesapeake
809 Live Oak Drive, Suite 21, Chesapeake, VA 23320
Visit WebsiteLicense: 591569

Expertise.com Rating

Review Sources

Google
4.5 (10)
Yelp
4.0 (4)

Why choose this provider?

Mike Bettencourt is one of the 19,000 State Farm agents spread across the country. Based in Chesapeake, he assists clients in finding health insurance plans, including individual medical, supplemental health, and Medicare Supplements. He also advises people considering short-term and long-term disability policies. Protection for life, such as term, permanent, and universal insurance, is available. Bettencourt is a Hampton Roads native helping customers transfer policies into their new address in Chesapeake. State Farm has been serving communities since 1922.

  • Life Insurance
  • Health Insurance

Compare our Top Health Insurance Agencies

NameExpertise RatingAddressPromotionsLearn more
Choice Insurance Agency
809 Greenbrier Parkway, Chesapeake, VA 23320
Towne Benefits
3 Commercial Place, Norfolk, VA 23510
We Insure
517 Baylor Court, Chesapeake, VA 23320
Brown & Brown Insurance
4500 Main Street, Virginia Beach, VA 23462
Mike Bettencourt
809 Live Oak Drive, Suite 21, Chesapeake, VA 23320

Chesapeake, VA Health Insurance FAQs

  • Who qualifies for Chesapeake's Medicaid program?

    Medicaid applications are accepted from Chesapeake residents who live in Virginia, are between the ages of 19 and 64, and do not qualify for or are not enrolled in Medicare. If you are unsure whether you are eligible, you can use the eligibility screening tool, which is available at https://www.coverva.org/screening. Applicants who meet the eligibility requirements may apply by phone, mail, or online.

  • What services does Medicaid cover in Chesapeake?

    Medicaid in Chesapeake covers a variety of services, including hospital, doctor, and emergency services. Furthermore, it includes prescription drugs, maternity and newborn care, laboratory and X-ray services, physical and speech therapies, and home health care. It also offers preventative wellness services like immunizations, wellness exams, nutritional counseling, and smoking cessation classes.

  • What is covered by a Chesapeake hospital indemnity insurance plan?

    The coverage provided by your Chesapeake hospital indemnity insurance will be determined by the type of plan you choose. Most plans cover inpatient stays as well as ICU or CCU confinement. Aside from ambulance services and emergency rooms, some hospital indemnity plans may cover outpatient diagnostic imaging techniques, outpatient X-rays and laboratory treatments, continuous care, and outpatient surgical procedures. Furthermore, hospital indemnity insurance pays a daily benefit amount for each hospital stay. This daily payment is made by the insurance company for a maximum of one year.

  • Are health insurance benefits available to Chesapeake City's full-time employees?

    Yes, full-time employees of the City of Chesapeake are eligible for Optima Health health insurance coverage. The three types of medical coverage provided by the City to its employees are point-of-service (POS), health maintenance organization (HMO), and consumer driven health plan (CDHP). All premium payments are deducted before calculating tax liability.

  • What is the distinction between COBRA and short-term health plans in Chesapeake?

    The Consolidated Omnibus Budget Reconciliation Act allows Chesapeake workers and their families to continue receiving group health benefits from their plan for a set period of time after losing their job, having their hours reduced, switching jobs, dying, getting divorced, or experiencing other life events. Meanwhile, short-term insurance covers emergency hospital visits, certain prescriptions, and doctor's appointments that are not related to pre-existing conditions.