Ryan MichalekWisconsin · Licensed independent broker

Wisconsin Health Insurance Built Around Your Life

Looking for a self-employed health insurance broker in Wisconsin? I’m Ryan Michalek, an independent health insurance broker for self-employed people, licensed in Wisconsin (one of the 31 states I’m licensed in), NPN 21043091. Individual-market rates in Wisconsin average about a 21.7% increase for 2027 (checked November 5, 2026). Anyone earning over the subsidy line (about $63,840 for one person) pays the full price, so I compare private under-65 plans side by side with full-price marketplace coverage. See Wisconsin’s 2027 numbers

From dairy country to Milwaukee's small business community, a lot of Wisconsinites are self-employed or run family operations and need their own health coverage. I help self-employed folks, 1099 contractors, families and small businesses find private under-65 plans that fit, in Milwaukee, Madison, Green Bay, Kenosha, Appleton and the towns between.

Open Enrollment for 2027 coverage

Wisconsin enrolls through HealthCare.gov, so 2027 Open Enrollment runs November 1, 2026 through January 15, 2027, and a plan picked by December 15 starts January 1. Two things changed at once this year: the enhanced subsidies that softened Wisconsin premiums through 2025 are gone, and the Office of the Commissioner of Insurance put the 2027 marketplace increase at a weighted 21.7%. If your household income sits anywhere near the cutoff, rebuild the estimate before your plan rolls over. See the full 2027 Open Enrollment guide or run your numbers in the estimator.

Ryan Michalek

Who you’ll talk to

Me, Ryan Michalek, not a call center. I’m licensed in Wisconsin, NPN 21043091. I answer my own phone, evenings and weekends included, and there’s no fee to work with me.

“Ryan was very helpful and made switching insurance plans simple and seamless. He’s professional and always answers my calls/texts within minutes. It’s refreshing to talk with someone who genuinely cares!” — Christina, Google review

“Very diligent and I always felt like a priority. Very glad to have connected with Ryan!” — Cameron M., Google review

Get my Wisconsin options

How health coverage works in Wisconsin

Wisconsin uses the federal HealthCare.gov marketplace for ACA plans, which are guaranteed-issue and subsidy-eligible if you qualify. Still, many self-employed Wisconsinites who earn too much for a subsidy want another option to weigh against it. Private under-65 plans often offer PPO-style flexibility and year-round enrollment. I compare both and tell you plainly which fits your situation. For 2027, the marketplace in Milwaukee offers no PPO plans at any metal level, only HMO networks (public marketplace quotes checked October 31, 2026). Can you still get a PPO in 2027?

Where the marketplace PPOs are in Wisconsin. Only 15 of Wisconsin’s 72 counties have a marketplace PPO for 2027: Brown, Outagamie, Winnebago, Waupaca, Waushara, Shawano, Oconto, Kewaunee, Menominee and Florence in the northeast, and Burnett, Douglas, Pierce, Polk and St. Croix in the northwest. Milwaukee, Dane, Waukesha, La Crosse and Marathon have none. The lowest-priced, about $1,059 a month for a 60-year-old, is in Brown County.

Sources: CMS marketplace plan data for 2027 (QHP Landscape, individual medical, data.healthcare.gov, updated October 30, 2026); age 60, no subsidy; checked November 12, 2026.

What the 2027 plan data shows in Wisconsin. Madison is one of the few places in Wisconsin where gold undercuts silver for 2027. In Dane County the lowest-priced gold plan for a 60-year-old is about $1,276 a month, about $107 under the $1,383 benchmark silver, and Columbia, Green and Sauk counties show the same pattern. Dane also runs about 13% below Milwaukee. Near Madison? I’ll price gold first.

Sources: CMS marketplace plan data for 2027 (QHP Landscape, individual medical, data.healthcare.gov, updated October 30, 2026); age 60, no subsidy; checked November 12, 2026. See every county’s 2027 numbers.

If you lose job-based coverage in Wisconsin. Wisconsin's continuation law lets you keep an insured group plan if you were covered 3 months and elect it within 30 days of notice; after 18 months, the insurer can require a move to individual coverage (Wis. Stat. 632.897). Wisconsin hasn't taken the federal Medicaid expansion, but BadgerCare covers adults up to the poverty line.

Sources: Wis. Stat. 632.897; KFF; checked November 12, 2026.

More Wisconsin rules that change the answer. Wisconsin protects former spouses more than most states. A group plan can't drop a spouse after a divorce or annulment if they choose to continue it, and there's no set end date, though the insurer can require a move to individual coverage after 18 months (Wis. Stat. 632.897).

Sources: Wis. Stat. 632.897; checked November 12, 2026.

Milwaukee, Madison, and Wisconsin’s independents

Wisconsin runs on manufacturing and small business, and that’s most of my work here. Milwaukee anchors a deep manufacturing and trades economy, and the machine shops, contractors and family firms that supply it are a 1099 world. Madison brings the university, biotech, and a growing startup scene; the Fox Valley its paper and manufacturing base; and the rest of the state its dairy and ag economy, where family farms buy their own coverage. For self-employed Wisconsinites who earn too much for a subsidy, I put the marketplace and private under-65 plans next to each other on your real numbers.

Wisconsin, from the lakeshore to the Northwoods

Wisconsin isn't one market. The price of a plan, how many insurers sell in your county and what kind of network you can buy all shift as you drive from Lake Michigan to the Mississippi. These are the 2027 figures from my own price checks (benchmark silver plan, one 60-year-old non-smoker, no subsidy, public marketplace quotes checked November 1, 2026), plus the Census numbers behind each region.

Map of Wisconsin places named on this page, with 2027 benchmark silver pricesOutline map of Wisconsin marking Milwaukee, Wausau and La Crosse (priced in the MHS 2027 check) and Kenosha, Madison, Oshkosh, Green Bay, Marinette, Eau Claire and Hudson. Benchmark silver for a 60-year-old, no subsidy, per month for 2027: Milwaukee about $1,588; Wausau about $1,589; La Crosse about $1,514.MilwaukeeKenoshaMadisonOshkoshGreen BayMarinetteWausauEau ClaireHudsonLa CrossePriced in my 2027 checkNamed in this sectionBenchmark silver, age 60, per month, 2027Milwaukee$1,588Wausau$1,589La Crosse$1,514

Benchmark silver for a 60-year-old non-smoker, before any subsidy, per month for 2027: Milwaukee about $1,588; Wausau about $1,589, with three insurers, down from four; La Crosse about $1,514. Source: MHS 2027 price check, November 1, 2026. Map: places this section names, on the U.S. Census Bureau 2023 state outline.

  • Milwaukee and the southeast. That plan runs about $1,588 a month in Milwaukee, up about 13% from 2026, with three insurers and no PPO at any metal level. Kenosha, Racine and Beloit sit on the Illinois line, and plenty of people there work in greater Chicago or Rockford. An individual plan generally follows the state you live in, so a Kenosha resident buys a Wisconsin plan and then checks whether its network reaches the doctors near the job. If home is on the other side, see Illinois health insurance.
  • Madison and Dane County. The capital and the university give the Madison area the highest median household income of the Wisconsin metros I track, about $91,100 (Census ACS 2025, table B19013). About 35 of every 100 Madison-area adults aged 19 to 64 who buy their own coverage have household income at or above 400% of the poverty level (table B27016), which means no 2027 subsidy and the full marketplace price.
  • Green Bay and the Fox Valley. It's paper mills, manufacturing and the shipping trades around Green Bay, Appleton and Oshkosh. About 9 of every 100 people under 65 in the Green Bay metro buy their own coverage, among the higher shares of Wisconsin's metros, behind Oshkosh-Neenah (about 11.5) and Kenosha (about 9.2) (table B27005). After the July 27 tornadoes, FEMA declared a major disaster (DR-4949, October 7, 2026) covering Outagamie and Winnebago counties, along with Forest and Vilas up north. If storm damage kept you from enrolling or changing plans on time, HealthCare.gov lists a natural disaster as a situation that may open a special enrollment period.
  • Wausau and central Wisconsin. This is the biggest one-year jump I found in the state: the Wausau benchmark rose about 18.5% to about $1,589 a month, now about the same as Milwaukee. Insurers in Marathon County fell from four to three, and the plan menu shrank from 46 plans to 28, none of them a PPO.
  • La Crosse, Eau Claire and the Driftless. La Crosse ran about $1,514 a month, about 5% below Milwaukee, with three insurers and no PPO. Along the St. Croix, many Hudson and River Falls households commute into the Twin Cities; as a Wisconsin resident you still buy a Wisconsin plan, so the question to settle is whether its network crosses the river with you. For the Iowa side of the Mississippi, see Iowa health insurance.
  • The Northwoods and the Michigan line. It's resort towns, timber country and long drives between hospitals. Logging is almost four times as large a share of Wisconsin's businesses with no paid employees as it is nationally (Census Nonemployer Statistics 2023, NAICS 113), and those owners buy their own plans. Up here the network matters more than the logo, so I check the nearest hospital first. Marinette and the Upper Peninsula trade back and forth across the Menominee River; for the Michigan side, see Michigan health insurance.

Wisconsin livelihoods that come with their own coverage questions

  • Dairy and crop farm families. Agriculture is about twice as large a share of Wisconsin's businesses with no paid employees as the national share (Census Nonemployer Statistics 2023), and a milk check that swings with prices makes the subsidy estimate the hard part. More in health insurance for farm families.
  • Owner-operator truckers. Wisconsin employs heavy and tractor-trailer drivers at about 1.4 times the national rate (BLS Occupational Employment and Wage Statistics, May 2025). Drivers who go out on their own lose the fleet plan the same week; see coverage for owner-operator truckers.
  • Tavern and supper club owners. Bars and taverns make up about three times the national share of Wisconsin's businesses with no paid employees (Census Nonemployer Statistics 2023, NAICS 7224). The owner behind the bar is usually the one without a group plan; how LLC and S-corp owners handle their own coverage.
  • Builders, electricians and the trades. Milwaukee's contractors and the small shops that feed its manufacturers run largely on 1099 work. See health insurance for tradespeople.
  • New business owners. High-propensity business applications in Wisconsin, the ones Census flags as likely to become employers, ran about 11% ahead of a year earlier in the three months through September 2026 (Census Business Formation Statistics). A new LLC usually means a first year of buying your own coverage.

A self-employed health insurance broker in Wisconsin, for anyone over the subsidy line

The short answer: Wisconsin uses HealthCare.gov, and the subsidy line is federal. Above 400% of the poverty level there's no premium tax credit for 2027, so you pay the full rate. For 2027 coverage that line is about $63,840 for one person or $86,560 for a couple, based on the 2026 HHS poverty guidelines (as of November 2026). That's where an independent broker who prices both sides is worth a call.

  • 2027 rates in Wisconsin. Fourteen companies filed individual-market rates for 2027 with the Wisconsin Office of the Commissioner of Insurance. healthinsurance.org's enrollment-weighted average of those filings is about a 21.7% increase (as of October 31, 2026). Your own number depends on your county, age and plan.
  • Wisconsin's reinsurance cushion. The Office of the Commissioner of Insurance says marketplace rates rose a weighted 21.7% for 2027 and would have risen about 33% without the Wisconsin Healthcare Stability Plan, the state's reinsurance program. Twelve insurers are on the marketplace for 2027, two more sell outside it, and none is leaving the state (OCI, October 30, 2026).
  • Your neighbors over the line. In 2026, about 33,000 Wisconsinites who picked a HealthCare.gov plan reported household income above 400% of the poverty level, down from about 48,000 in 2025 (CMS Open Enrollment state-level public use files). That's a drop of about 15,000 full-price buyers in a single year.
  • Short-term plans in Wisconsin. Wisconsin law lets a short-term plan run up to 12 months per term and 18 months in a row with the same insurer (Wis. Stat. 632.7495(4)); a 2024 federal rule sets a shorter limit (3 months, 4 with renewals), though federal agencies have said they are not prioritizing its enforcement. Either way it can bridge a gap but isn't a long-term answer. How short-term health insurance works.
  • How Wisconsin is set up. Wisconsin didn't adopt the ACA Medicaid expansion (KFF), but BadgerCare Plus covers adults with income up to 100% of the poverty level (Wisconsin DHS). If your income is low, that's the first door to check. I don't handle Medicaid or marketplace enrollment, but I'll point you to the right help.
  • Buying your own plan? If you're shopping for coverage outside a job, see Wisconsin individual health insurance for how individual plans work here.
  • Where to go next. Covering a family on self-employed income · COBRA alternatives when a job plan ends · what the 2027 subsidy cliff means for your income.
Wisconsin 2027 rate changeStatewide weighted average marketplace rate change for 2027: about +21.7%. Benchmark silver plan for a 60-year-old, no subsidy, change from 2026: Milwaukee about +13%; Wausau about +18.5%.2027 change in WisconsinStatewide weighted average rate change+21.7%Milwaukee benchmark silver, age 60, vs 2026+13%Wausau benchmark silver, age 60, vs 2026+18.5%

Wisconsin's 2027 marketplace rates rose a weighted 21.7% and would have risen about 33% without the state's reinsurance program (Wisconsin Office of the Commissioner of Insurance, October 30, 2026). The benchmark silver plan for a 60-year-old with no subsidy is up about 13% in Milwaukee and about 18.5% in Wausau from 2026 (MHS 2027 price check, November 1, 2026).

If your Wisconsin renewal letter for 2027 just arrived, the renewal increase check shows the change per month, per year and in percent before you decide whether to keep that plan.

I answer my own phone, evenings and weekends included. If a marketplace plan or the coverage you have now fits you better, I'll tell you plainly.

Figures as of November 2026. Sources: HHS 2026 poverty guidelines (400% line, multiplied out); Wisconsin Office of the Commissioner of Insurance (2027 rate filings list, updated October 22, 2026); healthinsurance.org 2027 rate tracker; KFF (Medicaid expansion status); Wisconsin DHS (BadgerCare Plus income limits); OCI 2027 marketplace preview (October 30, 2026); CMS 2025 and 2026 Open Enrollment state-level public use files; Wis. Stat. 632.7495(4); FEMA DR-4949; Census ACS 2025 1-year tables B19013, B27005 and B27016, Nonemployer Statistics 2023 and Business Formation Statistics; BLS OEWS May 2025. Regional prices are my own public marketplace quotes, checked November 1, 2026.

Who I help across Wisconsin

  • 1099 contractors and the self-employed who have to shop for their own plan
  • Individuals and families looking for coverage outside an employer, from Milwaukee to the Northwoods
  • People losing COBRA, or between jobs, who need something in place without a gap
  • Small business owners covering themselves and the folks on their crew
  • Early retirees bridging the years until Medicare picks up

Independent and still here after you enroll in Wisconsin

I work for you, not for one insurer, so I compare your real options and recommend what fits. I already work with clients in Wisconsin, by phone and video, from the southeast corner to the Northwoods. You get one licensed advisor from start to finish, and that advisor is me, Ryan Michalek, licensed in 31 states including Wisconsin (NPN 21043091). You can check my Wisconsin license yourself: the Office of the Commissioner of Insurance lookup tools page opens the licensee search; pick Wisconsin and search NPN 21043091.

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Wisconsin questions

Quick answers for Wisconsin.

Can I buy coverage in Wisconsin outside open enrollment?

Marketplace coverage generally runs on that once-a-year clock, though qualifying events, like leaving a job, a marriage or a new dependent, can open a short special enrollment window. On the private side, plenty of under-65 options enroll year-round, so being outside open enrollment doesn't always mean you're out of luck.

Do you serve all of Wisconsin?

Yes, all of Wisconsin. From Milwaukee and Madison up to the Northwoods, I meet with people by phone and video, so distance has never been an issue.

What does a Wisconsin health insurance agency do that HealthCare.gov doesn't?

HealthCare.gov shows you marketplace plans. As an independent Wisconsin broker, I also price private under-65 plans beside them, check your doctors, and tell you which fits your income. If a marketplace plan with a subsidy is the better fit, I'll say so and help you find the right place to enroll.

Is there a health insurance broker in Milwaukee for self-employed people?

Yes. I work with self-employed people, 1099 contractors and small-business owners in Milwaukee, Madison, Green Bay and across Wisconsin by phone and video. There's no fee to you, and I'll tell you plainly if the marketplace is the better fit.

Is there a fee to work with you?

No. The carrier pays me once you're enrolled, not you. So there's no bill from me, whether we find you a plan right away or it takes a few conversations.

Who is a good self-employed health insurance broker in Wisconsin?

One who knows Wisconsin’s own-boss economy. Bars and taverns make up about three times the national share of Wisconsin’s businesses with no paid employees, and in Milwaukee the 2027 benchmark silver plan for a 60-year-old with no subsidy runs about $1,588 a month, with no PPO at any metal level. I’m licensed in Wisconsin. For tavern owners, Milwaukee contractors and dairy families over the subsidy line, I compare private under-65 plans, which are medically underwritten, with full-price marketplace coverage. There’s no fee to work with me.

What is the Wisconsin Healthcare Stability Plan, and does it lower my premium?

It's Wisconsin's reinsurance program, and it holds down the price of individual-market plans in the state, so it helps you whether or not you get a subsidy. You don't apply for it; it's built into the rates. The Office of the Commissioner of Insurance says 2027 marketplace rates rose a weighted 21.7% and would have risen about 33% without it (October 30, 2026). If you earn over the subsidy line, I'll put that price next to private under-65 plans so you can see both.

Is health insurance more expensive in rural Wisconsin than in Milwaukee for 2027?

Not by much, in the areas I checked, but the choices are thinner. For a 60-year-old with no subsidy, the benchmark silver plan was about $1,589 a month in Wausau, about the same as Milwaukee's $1,588, and about $1,514 in La Crosse. Wausau's price rose about 18.5% from 2026 and Marathon County lost one of its four insurers. None of the three areas had a marketplace PPO. Prices from public marketplace quotes checked November 1, 2026; yours depend on your ZIP, age and plan.

Why can’t I find a PPO on the marketplace in Milwaukee?

Because there isn’t one for 2027. I checked public marketplace quotes for Milwaukee on October 31, 2026 and found HMO plans only, at every metal level. Wausau and La Crosse showed no PPO either. If you’re a dairy family, tavern owner or contractor whose doctors span more than one system, private under-65 plans often run on PPO-style networks. They’re medically underwritten, so approval isn’t automatic. Text me your county and the names of your doctors, and I'll check.

Call, and it's me on the line. No script and no spam, just a real person with time to talk it through.

In their words

“Ryan was super helpful in getting our insurance plan created! He was informative, prompt, and insightful on the process and helping us understand what our plan entails. I highly recommend anyone looking for insurance to have Ryan guide you through the process because he will take care of you and make sure that you are happy with the end result!”

— Amber M.

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Reach out and I'll lay your Wisconsin choices side by side, from dairy country to Milwaukee. What day and time works best for a 15-minute call?

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Send your info and I’ll compare your real Wisconsin options on your actual numbers, with no fee and no rush. Prefer to talk? I’ll call you.

This is educational and general — not an offer, quote, or guarantee of coverage. It names no carriers. Any premium figures shown are dated public benchmarks for reference, not a quote. Nothing here is legal, tax, or financial advice.

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