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The United States’ health insurance system is woefully entangled with traditional employment. In 2019, 55.4% of insured individuals received their insurance through their employer.[1] If you’re a business owner or freelancer that doesn’t qualify for Medicare or Medicaid, you’ll have to do a lot of extra work to find the best health insurance for the self-employed.

To help you get started, use this list of some of the best insurance providers for individuals. Try not to purchase plans from the companies directly, though. Just keep them in mind when perusing or your state’s marketplace. 

📕 Required Reading: Are you still a little unsure how this whole health insurance thing works for people that run their own business? If so, check out our introduction to the process before reading further: How to Get Health Insurance While Self-Employed.


While the Affordable Care Act (ACA) created a national healthcare marketplace, plans are still specific to your state – even your zip code. After all, you need to purchase one based on the service providers that are within driving distance.

Because of this, it’s impossible to recommend the best health insurance plans for the self-employed. It’s far too specific, and which one you choose will depend on your state, your needs, and the quality of the network near you.

Instead, this is a list of insurance providers that offer consistently superior health insurance. They’re among the best places to start when shopping for a plan.

When selecting them, I considered the following criteria:

  • Prices: Healthcare costs are always going to vary considerably across different locations, but I prioritized insurance providers with a reputation for lower premiums and deductibles in multiple states.[2]
  • Accessibility and Network: Most insurance companies operate in limited locations. I prioritized those with large networks and coverage in multiple states and countries. An insurance company that only serves Ohio won’t ever be the best health insurance for the self-employed.
  • Bonus Benefits: Many of the best providers offer more than just basic health insurance. They may offer enhanced telecare, preventative services, reward programs, and supplemental plans.
  • Reputation for Customer Satisfaction: Health insurance is a service business, and customer satisfaction is one of the most crucial intangibles. I selected companies that have established a precedent of making their customers happy.
  • Financial Stability: Insurance companies are a business like any other, and they can fail. If they go under or can’t afford to pay out claims, you might be out of luck. I chose companies that have demonstrated that they’re not in danger of disappearing on their customers.

Keep in mind that these are just recommendations to help start your search. These companies may have hundreds of plans in your state, and not all of them will fit your needs. Study the specifics before purchasing one.

1. United Healthcare

🏆 Accessibility and Network


  • Largest national network of providers
  • Valuable extra benefits for members
  • Supreme financial stability


  • Less competitive on price than others on this list
  • Mixed levels of customer satisfaction

United Healthcare is one of the best-known healthcare providers in the country. Founded in 1977, they became the nation’s biggest health insurance provider in just a few short decades.

A subsidiary of UnitedHealthcare Group, the health insurance provider has the single largest market share at 14.1% in 2021.[3] They offer plans in all 50 of the United States and 130 countries. In 2020, their network boasted over 6,500 affiliated hospitals and more than 1.3 million service providers.

If you’re one of those wandering freelancers who bounces from state to state or even plans to live abroad for a time, United Healthcare is a great company to use. Whenever you move somewhere new, you won’t have to deal with searching for a new provider.

In addition to their top-notch network, United Healthcare has some appealing benefits for members, such as:

  • Reward programs for healthy preventative behavior.
  • The UHC App, which lets members manage everything in one convenient place.
  • The ability to chat with a doctor online 24/7.

From a financial standpoint, United Healthcare is rock solid. They received a Financial Strength Rating of A from AM Best in 2020 and an A+ for their Long-Term Issuer Credit Rating.

Unfortunately, their plans can be more expensive than the equivalent offerings from their competitors. As a quick measuring stick, United Healthcare doesn’t have the cheapest silver health insurance plan in any of the 50 states.[4]

With such a large customer base, it’s not surprising that they also have mixed customer reviews and levels of satisfaction. UnitedHealthcare didn’t win any of the regions on the J.D. Power Survey in 2020, but they average just under four stars on Consumer Affairs.

2. Cigna

🏆 Most Convenient


  • Premier virtual experience for members
  • Strong financial outlook
  • Widely affordable coverage


  • Limited availability and network size
  • Mixed levels of customer satisfaction

Cigna is another titan in the health insurance industry. They have one of the longest track records in the business and have been providing services since 1792. They’re another provider with a significant market share, millions of customers, and a vast global network.

Their most significant appeal comes from their emphasis on technology, convenience, and innovation. The whole industry has been transitioning toward virtual care since the pandemic, but Cigna’s plans have included 24/7 access to virtual care for much longer.

Beyond that, Cigna also has a strong financial outlook. After all, they’ve been able to remain in business for over two centuries. Unsurprisingly, A.M. Best gave them a Financial Strength Rating of A, which is excellent.

Cigna’s plans are also on the more affordable side of the spectrum. They only operate in a dozen states, but they offer the cheapest silver plan on the market in three of them. 

Speaking of which, their main drawback is probably the fact that their health insurance plans are only available in twelve states. Other than that, their customer reviews are also mixed. They only have a 3.5 out of 5 stars rating from Consumer Affairs, but they did well in the J.D. Power Survey, including one regional first place.

3. Oscar

🏆 Up and Coming


  • Excellent customer service and satisfaction
  • Growing, with lots of potential
  • Top-tier digital and remote services


  • Unproven financial stability
  • Limited geographical availability
  • Middling price point

Oscar is virtually brand new compared to many of the other companies on this list. They just started doing business in 2012, but they skyrocketed to the heights of the top competition. They now have over 250,000 members and a rapidly growing provider network in nine states, with more on the way.

Oscar’s startup status is a significant part of what makes them so attractive. They’re a young company and have the fire that often comes with meteoric rises. They can provide:

  • Personalized care and stellar customer service through their concierge program
  • The ability to communicate with doctors remotely at any time 
  • A uniquely modern approach to connecting with members through technology

Of course, their youth is a strength, but it’s also their weakness. They don’t have the decades-long track record of some of their competitors, and they’re too new for A.M. Best to rate their finances. Because they’re still so new, they’re not accessible in as many states as a provider like United Healthcare.

Oscar plans also usually fall somewhere around the middle of the pack when it comes to price. They have affordable plan options, but members may have to pay more for better care.

Much like with Cigna, self-employed people will probably appreciate Oscar’s dedication to leveraging technology and convenience. They’ll undoubtedly continue to innovate as they grow in the coming years.

4. Kaiser Permanente

🏆 Best Value


  • Top-tier pricing and affordability
  • Seamless access to great care with their integrated systems
  • Tremendous customer satisfaction ratings
  • Strong financial outlook


  • Only available in select states

Kaiser Permanente is a unique entry on this list. While they are an insurance provider, they also have their own facilities and providers. That integrated system allows them to offer seamless referrals and provide supremely smooth access to care.

Kaiser also boasts super customer satisfaction levels. They have a rating of four stars on Consumer Affairs and ranked number one in 5 of the 21 regions on the J.D. Power Survey in 2020. 

Their prices are also much more affordable than it seems like they should be, given their premier service. They have the cheapest silver plans in four states, which is the third most in the nation. 

Kaiser’s financial outlook is also top-notch. They finished 2020 with a net income of $6.4 billion, and they rank number seven in market share despite operating in a relatively small geographical range.

Speaking of, that’s the only real downside to Kaiser: They’re only available in eight states. But if you live in a region that they cover, a Kaiser plan is very likely your best option. 

5. Blue Cross Blue Shield

🏆 Old Faithful


  • Top-tier network and availability
  • Balanced pricing and affordability
  • Stable financially and long-established
  • Solid customer satisfaction and reputation


  • Potential inconsistency in various parts of the country

Last but not least, there’s Blue Cross Blue Shield. They’re another corporate giant with well-rounded value. They’re among the best in just about every category, so there’s not much to complain about when it comes to their services.

In addition to being a jack of all trades, they might also be the most affordable option in the country, on average. They offer the cheapest silver plans in a whopping nine states, which is the most in the nation. If you’re looking for the best prices, Blue Cross Blue Shield is the place to start your search.

They also have one of the biggest nationwide networks, contracting with 96% of hospitals in the country and 95% of its service providers. They have coverage in all 50 states and serve over 100 million members worldwide. Many of those are in the other 170 countries where they provide coverage.

They also receive solid customer satisfaction scores, coming out on top in 7 of the 21 regions on the J.D. Power Survey. That’s a full third of the country, and more than any of their competitors.

The only drawback to Blue Cross Blue Shield is the potential inconsistency between branches. The provider is actually a conglomerate comprised of 36 distinct companies. Their quality and services may vary significantly between them, so check out their reputation in your state before doing business with them.

Keep an Open Mind and Get Help

There’s never going to be a single best health insurance for the self-employed. It’s always going to depend on your personal circumstances, including your age, health, family, and location. Start your search with these recommendations if possible, but don’t limit yourself if they’re not available near you.

If you find the process of searching for your own plan overwhelming, don’t be afraid to get help from people who are experts in the field. A local health care advisor can help you navigate the complexities, make recommendations, and answer your questions.

📘 Learn More: Are you doing your research before transitioning to full-time entrepreneurship? Take a look at our guide to the process to help you navigate the other issues you’ll run into: How to Start a Business While Working Full-time (And Replace Your Job)