The Ultimate 2025 Guide to Freelance Health Insurance

If you identify as a gig worker, freelancer, fractional worker, independent contractor, solopreneur, entrepreneur, creative worker, or just consider yourself self-employed, the task of securing freelance health insurance often falls solely on your shoulders.

Whether it’s your first time in this process or you’re a veteran freelancer, we’ve got the guide to the most reliable and affordable healthcare options for you.

Understand Freelance Healthcare 101

Since healthcare is often tied to employer-sponsored benefits in the United States, freelancers and independent workers are left to find Individual Health plans for themselves. If you’re already familiar with the way freelance healthcare works, SKIP AHEAD to your options. If you’re new to the individual healthcare world, read on!

There are two ways to enroll in health insurance as a freelancer: on the government marketplace, or with a private insurer. For some independent workers, enrolling on the marketplace can be less costly, though plans may not be as comprehensive.

For other workers, enrolling with an insurer like HBG Solo may make more sense cost-wise and be a better plan. For some individuals (especially those with S-Corps), getting insured through a full-benefits platform like Opolis can help them get premium coverage while saving thousands of dollars.

Before we learn more about each option available to you, let’s take a minute to learn about some of the terminology associated with health insurance.

Learn some of the terminology

associated with health insurance plans

There are several different types of costs associated with insurance plans:

  • Premium: This is the monthly fee you pay to have insurance coverage.
  • Copay: A fixed dollar amount that you pay out of pocket for a medical expense until you have reached your out-of-pocket maximum. Insurance companies normally charge either copays for most services other than specific preventive health ones.
  • Deductible: The annual amount you are responsible for paying toward medical expenses before your insurance coverage “kicks in” to pay the rest. Although copays apply towards your deductible, you will still be charged copays after you have reached your deductible.
  • Maximum out-of-pocket: This is the maximum amount you will be responsible for paying toward medical expenses covered on your plan. Once you have reached this amount, you will not be charged for additional eligible medical expenses
  • Marketplace: The Health Insurance Marketplace, also known as the exchange, is a platform established under the Affordable Care Act (ACA) that enables individuals and families to compare and purchase health insurance plans.
  • Open enrollment: This is the crucial time of year when you can enroll in or make changes to healthcare plans on the federal and state marketplace. Beginning November 1st, 2024 and running until January 15th, this is your opportunity to secure the coverage you need for the upcoming year.

To help understand your health insurance plan, read our glossary of health insurance terms.

The overall cost of your health insurance plan is typically a combination of the various pricing factors listed above. For example, plans with higher premiums (monthly payments) will frequently have lower copays and deductibles. If you expect to have high medical expenses in the next year, you may want to sign up for a plan with a higher premium and lower copays.

Make a list of things that are vital 

to your healthcare plan

Be sure to consider your medical and financial needs. For example, if you are relatively young and healthy, you might want to select a high-deductible or catastrophic plan. If you have a chronic medical condition, a plan with a more expensive premium but lower out-of-pocket costs might work better for you.

You can take our custom Health Insurance Survey to find out what the best health insurance plans are for you. Additionally, you can sign up to get a free one-on-one consultation from HBG Solo, benefits platform Opolis, or MetroPlusHealth (NY State Only) to discuss your needs with a live representative.

Understand your options for 

low cost care

You might be eligible for a free or heavily subsidized health plan based on a number of factors. Read here to find out if you’re eligible.

There are several government programs that may offer free or extremely low-cost coverage. These include:

  • Veterans Health Administration (VA): If you or your spouse is a veteran, you may be eligible for free VA health care.
  • Medicare: If you are 65 or older, have end stage renal disease, or qualify for social security disability payments, you are eligible for Medicare.
  • Medicaid: If your modified adjusted gross income is below 100 or 138 percent of the Federal Poverty Level (depending on your state of residence) for your size of household, you are eligible for Medicaid and ineligible for ACA subsidies
  • Children’s Health Insurance Program (CHIP): If you do not qualify for Medicaid, your child may still be eligible for the low-cost CHIP program. Prices and eligibility vary by state.
  • Premium Tax Credits (ACA Subsidies): Before you shop for plans on exchanges, find out if your income qualifies you for subsidies in the form of premium tax credits.

If you don’t qualify for any of the above options, it is still important to get covered. At Freelancers Union, we have over 25 years of experience connecting freelancers to the right health insurance plans. You can take our survey to get a custom list of options tailored for your needs, or browse all of our health options to decide what works for you.

Important Dates to Know

Open Enrollment for Medicare begins on October 15th, 2024. For other plans, the Open Enrollment period runs from November 1 to January 15 in most states. For coverage starting on January 1, most people need to apply by December 15. Make sure to check your state’s details below!

Open Enrollment from Nov 1st to Jan 15th:

Alabama, Alaska, Arizona, Arkansas, Colorado, Connecticut, Delaware, Florida, Georgia, Hawaii, Idaho, Illinois, Indiana, Iowa, Kansas, Kentucky, Louisiana, Maine, Maryland, Michigan, Minnesota, Mississippi, Missouri, Montana, Nebraska, Nevada, New Hampshire, New Mexico, North Carolina, North Dakota, Ohio, Oklahoma, Oregon, Pennsylvania, South Carolina, South Dakota, Tennessee, Texas, Utah, Vermont, Virginia, Washington, West Virginia, Wisconsin, Wyoming

Open Enrollment from Nov 1st to Jan 31st:

California, District of Columbia, New Jersey, New York, Rhode Island

Open Enrollment from Nov 1st to Jan 23rd:

Massachusetts

Most states require you to enroll by December 15 if you need coverage starting January 1, 2024 and enrollment by January 15 for February 1 coverage.

What other options are available?

Now that you know what the different options are, click below to be directed to learn more about each one:

Browse the Health Marketplace

Catch simplifies government websites and allows you to easily compare plans on the federal and state marketplaces. Find the best plan at the best price, and ensure you’re getting any health insurance-related tax credits you might be qualified for.

Explore Catch

Explore Affordable PPO Plans

Solo Health Collective's innovative PPO plans offer affordable monthly premiums, full coverage after your deductible is met, and year round signups - no open enrollment period required.

Explore Solo

Get the Benefits of a W2 Employee

Opolis is a freelance employment and benefits platform providing affordable, premium group benefits, payroll, tax compliance, and more.

Explore Opolis

Health insurance FAQs

Have a question about health insurance

Even if you are young and healthy, you need insurance. One accident, illness, or injury could be financially devastating. While the federal penalty for not having health insurance is no longer in effect, D.C., Massachusetts, California, Vermont, Rhode Island, and New Jersey all enforce penalties that can range from under $300 to over $1,000 each year.

If your plan is ending, you can shop for a new plan during the current Open Enrollment period — which ends on January 15 — on our benefits platform or state exchanges.

Under the ACA, you may be eligible for a subsidy or tax credit toward your health plan if your modified adjusted gross income is between 100% and 400% of the federal poverty level for your household size and you are not eligible for Medicaid, Medicare, or employer-sponsored ACA-compliant insurance. If your income is below 100% or 138% (depending on your state of residence) of the federal poverty level, you are eligible for Medicaid rather than ACA subsidies. If you are 65 or older, you are eligible for Medicare rather than subsidies. To determine your eligibility, visit here. If you think you are eligible for a subsidy, our platform will connect you to your local exchange for relevant information.

Open Enrollment for 2023 coverage began on Monday, November 1, 2021, and runs until Wednesday, January 15, 2023, in most states. During this time, you can enroll in a new plan or change your current plan. States offering extended open enrollment periods include California, Colorado, Connecticut, Florida, Massachusetts, Minnesota, New York, Rhode Island, and Washington, DC. To make sure your coverage for 2023 is in place, you will need to enroll in and pay for a new plan by January 15, 2023.

Under the Affordable Care Act, insurance plans for individuals are offered at five tiers:

  • Catastrophic (available for those under age 30)
  • Bronze
  • Silver
  • Gold
  • Platinum

While higher tiers may be more expensive up front, that isn’t always the case, and the total amount you pay for covered services may be lower. Compare prices carefully in order to find the plan that offers the best value for your individual circumstances. While all ACA-compliant plans must offer the same 10 essential health benefits, some plans offer extra benefits that may be particularly valuable to you or your family. Also, plans may differ in which providers you can access, as well as certain preventive services and benefits. Compare plans in different tiers carefully before making your final selection, as you won’t be able to change insurance plans until the next open enrollment period.

Yes, but only if you qualify for a special enrollment period by:

  • Gaining or becoming a dependent
  • Losing existing health coverage (through job loss, separation from a spouse, etc.)
  • Expiration of COBRA
  • Loss of eligibility for or expiration of a student health plan
  • A permanent move or relocation to an area with different health plans
  • Dramatic change in income that affects your eligibility for tax credits or cost-sharing reductions.

If any of these special circumstances apply, you may be eligible to enroll for a limited amount of time after the event. If you don’t enroll during the open enrollment period and you don’t have a qualifying event, you will be unable to buy ACA health insurance until open enrollment in 2023, although you will still be eligible for Short-Term Health Insurance Plans.

The ACA made it illegal for insurance companies to deny you coverage, refuse to cover treatment, or charge higher premiums for pre-existing health conditions.

You have three options:

Our National Benefits Platform, which provides a curated selection of health insurance options for freelancers across the country.

Your state’s health insurance marketplace (you can see a directory of state exchanges and the federal exchange at healthcare.gov).

The websites of individual private insurance plans.

Start by viewing your options at https://freelancersunion.org/insurance/health.

If you have specific questions about a particular plan, call the insurer to get the best and fastest answer. You can find many insurer phone numbers on our website. You can also email us at membership@freelancersunion.org and we’ll respond as quickly as we can.

Get covered! It’s easier than you might think. You also can spread the safety net by sharing information about our National Benefits Platform to help your friends get health insurance, too.