Wisconsin Health Insurance — Built Around Your Life
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 individuals, the self-employed, 1099 contractors, families, and small businesses across Wisconsin — from Milwaukee, Madison, and Green Bay to Kenosha and Appleton — find private under-65 plans that fit.
Open Enrollment for 2027 coverage
For 2027 plans, Open Enrollment generally runs November 1, 2026 through January 15, 2027 — enroll by December 15 for a January 1 start (a few state-run marketplaces set their own dates, which I'll confirm for you). Worth knowing this year: the enhanced premium subsidies that held costs down through 2025 have scaled back, so many self-employed people in Wisconsin are seeing higher premiums for 2027 — if you're near the income cutoff, it's worth re-running your numbers rather than assuming last year's plan still fits. See the full 2027 Open Enrollment guide or run your numbers in the estimator.
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. But many self-employed Wisconsinites who earn too much for subsidies need an affordable alternative. Private under-65 plans often offer PPO-style flexibility and year-round enrollment. I compare both and tell you honestly which fits your situation.
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
An independent broker who's still there after you enroll
I work for you, not one insurer — comparing your real options and recommending what fits. One licensed advisor, start to finish. Licensed in 31 states, including Wisconsin. (Ryan Michalek, NPN 21043091.)
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 — leaving a job, a marriage, 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.
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.
Explore coverage by situation.
Self-employed & 1099
Buying your own coverage as a freelancer, contractor, or solo business owner.
Explore self-employed →Families & individuals
Coverage for your household, built around your budget and doctors.
Explore family coverage →COBRA & coverage gaps
COBRA ending, between jobs, or losing a plan? Move fast and avoid a gap.
See gap options →Moving to a new state
A move can open a special window — and your plan may not cross state lines.
What changes when you move →Covering a team? Explore small business & group coverage → · See all service areas →
A real person — not a call center. No spam calls, no robocalls, no pressure — just my number, and me on the other end.
Let's find your Wisconsin coverage.
Reach out and I'll compare your Wisconsin choices honestly — no scripts, no pushy sales.