Wisconsin open enrollment 2027 Open enrollment · Wisconsin

Wisconsin Open Enrollment 2027 for Small Business Owners

Last updated November 3, 2026 · By Frank Caballero, licensed health insurance broker

Short answer

For small business owners in Wisconsin, open enrollment for 2027 coverage runs November 1, 2026 to January 15, 2027 on HealthCare.gov, and December 15 is the date to choose by for a January 1 start. Your own coverage can also come from a private, medically underwritten plan, which does not wait for the window: if approved, it can start the first of any month.

What 2027 looks like for you

Wisconsin's average 2027 rate change is 21.7% (finalized). The details are on the Wisconsin 2027 premium increase page.

Group plans can renew at any point in the year, so open enrollment matters to owners for two reasons: an individual coverage HRA, or ICHRA, reimburses employees for individual plans they choose, and most of that shopping happens in this window; and an owner covering only the household buys in the individual market too. For your own household, the 2027 subsidy line is $63,840 for one person, $86,560 for two and $132,000 for four.

Wisconsin this year

Wisconsin's final individual increase averages about 21.7 percent for 2027, well above the roughly 13.3 percent average for small-group renewals. The individual market is the most crowded of any state I work in, with twelve insurers filing on HealthCare.gov, many of them regional plans tied to local health systems. State reinsurance has trimmed premiums for years, but this year's pressures outran it. A Milwaukee manufacturer, a Madison trades contractor, a Fox Cities trucking company or a Northwoods resort could see entirely different individual lineups for workers in different counties, and the group renewal holds a clear price edge.

Small-group plans in Wisconsin average about 13.3% for 2027, against 21.7% for individual plans, so put this year's group renewal next to an ICHRA quote before you sign it.

One thing to do before you choose

Before moving to an ICHRA, check individual plans county by county for your workers in Green Bay, Kenosha, Racine or the Northwoods, since regional insurers sell in limited areas. A dairy operation with workers in two counties may find completely different networks on each side of the line. If your group renewal comes back near 13 percent, give it serious weight before switching.

Your checklist

Your 2027 group renewal letter and its effective date
How many employees you have and where they live
A fixed monthly ICHRA budget you could offer
Your own household's coverage, priced separately

Private plan or Marketplace?

Private plan

For the owner's own household when everyone is healthy: priced on age, ZIP code and health. Approval depends on health answers; not an ACA Marketplace plan.

Marketplace

For employees on an ICHRA, or an owner with ongoing care: HealthCare.gov accepts everyone during open enrollment.

Compare Wisconsin plans this open enrollment

Private plans priced first, the Marketplace alongside when it fits. Phone or video, English or Spanish, no fee.

Get a quote Book a call (786) 218-2384

About your broker

Frank Caballero (NPN 21032307), licensed in 31 states including Wisconsin. Phone or video, English or Spanish, no fee; independent, not HealthCare.gov or any government agency.

Questions

When is the 2027 open enrollment deadline in Wisconsin?

January 15, 2027 on HealthCare.gov. Choose by December 15, 2026 for coverage that starts January 1; plans picked after that start February 1.

Do Wisconsin continuation rules cover my 5-person business?

Yes. Wisconsin makes insured group health plans of any employer size offer up to 18 months of continued coverage for members covered three months or more, capped at the full group rate. Departing employees have 30 days to elect after notice. Self-funded plans fall outside the Wisconsin law.

Can I get a private plan in Wisconsin after open enrollment closes?

Yes. You can apply in any month and, if approved, a private plan can start the first of a month; the insurer can decline based on health answers.

More for Wisconsin

Official sources: HealthCare.gov, the federal Marketplace; HealthCare.gov: special enrollment periods. FC Insurance Solutions is an independent, licensed brokerage and is not affiliated with any government agency.

Written by Frank Caballero, licensed health insurance broker in Wisconsin and 30 other states, NPN 21032307. Last updated November 3, 2026.