Best Cash Prize Sweepstakes in Madison, WI: 2026 Local Guide

If you live in Madison and want a real shot at cash, two current options stand out: the Saver's Sweepstakes prize-linked savings account at Heartland Credit Union on High Crossing Blvd, and United Way of Greater Milwaukee & Waukesha County's Give & Win drawing, which is open to every Wisconsin resident 18 or older through November 6, 2026. The first pays its prizes in cash drawings tied to money you keep; the second has a $12,000 top prize and accepts a mailed entry with no donation. Those are the two verified cash-prize openings for Madison savers and players right now, and both are chances to win rather than guaranteed payouts.

Below is what each one requires, where the entry caps sit, and why the state's old weekly cash drawing is no longer on the list.

Verification note: Program terms and availability can change. This page was checked against linked sources on October 21, 2026.

Heartland Credit Union's Saver's Sweepstakes: entries you earn by saving

A prize-linked savings account pays its reward as sweepstakes entries instead of, or alongside, ordinary interest. At Heartland Credit Union, headquartered at 5325 High Crossing Blvd in Madison, every $25 you deposit into the Saver's Sweepstakes account earns entries into monthly, quarterly and annual cash drawings, with prizes listed from $50 to $5,000 on Heartland's Saver's Sweepstakes page. Heartland also runs members-only drawings on top of the statewide pool: two $50 winners each month, two $100 each quarter and two $500 a year.

The limits matter as much as the prizes, and they sit in Heartland's own truth-in-savings addendum. Entries cap at 6 per month, 18 per quarter and 72 per 12-month saving period, so a large lump-sum deposit does not buy unlimited chances. A member may hold only one such account as first-named owner, the saving period runs a minimum of 12 months and auto-renews, and withdrawals reduce your entries.

That last rule is the one to plan around. This is a savings account you are meant to leave alone; if you expect to dip into the balance, your entry count drops with it.

The statewide pool behind the local account

Saver's Sweepstakes is run across Wisconsin by the Wisconsin Credit Union League, not by any single branch. According to the League's Saver's Sweepstakes FAQs, participation is limited to residents of Wisconsin, Illinois or Minnesota who are 18 or older, with some minor accounts eligible. Winners are drawn at random by TruLync, a subsidiary of the Minnesota Credit Union Network, and each credit union notifies its own winners by phone, email or mail.

The most recently published statewide prize pool was $120,000 for 2025: 75 monthly drawings of $100, five quarterly drawings of $1,000, one annual $5,000 drawing and ten $500 holiday drawings, with each participating credit union contributing according to its asset size. No 2026 pool table has been published, so this year's counts and amounts may differ from those figures. Treat the 2025 breakdown as the shape of the program, not as a promise of what 2026 pays.

Madison savers also have a second way in. Fort Community Credit Union participates in the same statewide drawings and has Madison branches on Rimrock Rd, Struck St and E Washington Ave, so joining a different credit union does not mean a different sweepstakes.

Give & Win: one free entry, a $12,000 prize, and a hard deadline

United Way of Greater Milwaukee & Waukesha County's Give & Win sweepstakes is open to all legal Wisconsin residents 18 or older, which includes Madison, even though the sponsoring United Way is based elsewhere. The 2026 official rules set the entry window from August 1, 2026 to 5:00 p.m. CST on November 6, 2026, and allow entry by mailed letter with no donation.

One entry per person. Read the first prize carefully before you count it as cash in hand: it is $12,000 toward the purchase or two-year lease of a vehicle from any Russ Darrow dealership. That is a substantial prize, but it is directed at a vehicle transaction, not a check you can spend on anything.

The window closes in about two weeks from today. A mailed entry has to arrive within it, so the practical deadline for Madison entrants is sooner than November 6.

What the Wisconsin Lottery offers now, and what it stopped

The Wisconsin Lottery is a state agency based in Madison, and its giveaways follow consistent rules: Wisconsin residents 18 or older, no purchase necessary to enter the giveaway, winners selected by random drawing. Its current Packers Bonus Drawing takes mailed non-winning 2026 Packers scratch or Fast Play tickets totaling at least $5 and awards 196 prizes, including 2027–28 club-seat season tickets, per the Lottery's prize giveaway page. Those are prizes, not cash, which is why it supports the list only as context.

The cash drawing Madison players used to have is gone. The weekly Super 2nd Chance Drawing paid ten $1,000 cash prizes a week to players who mailed in $5 of non-winning tickets, and it held its final drawing on December 26 after the Lottery pointed to outdated mail-in processing and rising postage costs. The Lottery said it had no plans to replace it, so there is no state-run cash second-chance drawing to enter today.

Note also that "no purchase necessary" is doing specific work in the Packers drawing. Entry into the drawing costs nothing extra, but the tickets you mail in were bought.

A judged contest is not a sweepstakes

One Madison cash opportunity is worth knowing about and worth classifying correctly. The Wisconsin Academy of Sciences, Arts & Letters, based in Madison, pays cash awards of $500, $250 and $100 in its Wisconsin People & Ideas fiction and poetry contests, open to entrants 18 or older who live in or attend school in Wisconsin. Two things separate it from everything above.

Winners are judged on the work, not drawn at random, and there is a per-entry fee — $10 for members and $15 for non-members in 2026. The next submission window also runs January 15 to March 31, 2027, so it is not an entry you can make this month.

How to choose between them

Before you open an account for the drawings alone, check the entry math. Six entries a month is the ceiling at Heartland regardless of how much you deposit, which means $150 a month reaches the cap and anything beyond it earns no additional chances that month.

• Want cash with no entry fee and no deadline pressure: open the Saver's Sweepstakes account at a participating Madison credit union, and plan to leave the balance in place for the full 12-month period.
• Want the largest single prize and the lowest effort: mail the free Give & Win entry before the November 6, 2026, 5:00 p.m. CST cutoff.
• Already buying Packers scratch tickets: hold the non-winning ones and mail $5 worth into the Bonus Drawing, but expect prizes rather than cash.
• Writing fiction or poetry: mark the January 15, 2027 opening for the Wisconsin Academy contests and budget the entry fee.

Frequently Asked Questions

Do I have to donate to enter Give & Win?

No. The 2026 official rules permit entry by mailed letter without a donation, limited to one entry per person.

Can I open Saver's Sweepstakes accounts at two credit unions to double my entries?

Heartland's addendum limits a member to one such account as first-named owner at that credit union. The drawings themselves are run statewide by the Wisconsin Credit Union League, so the entry caps apply to the account, not to the number of branches near you.

Who actually picks the Saver's Sweepstakes winners?

TruLync, a subsidiary of the Minnesota Credit Union Network, draws winners at random. Your own credit union then contacts you by phone, email or mail.

Is there still a Wisconsin Lottery cash drawing for non-winning tickets?

No. The Super 2nd Chance Drawing held its final drawing on December 26, and the Lottery said it had no plans to replace it. The current Packers Bonus Drawing awards prizes, including 2027–28 club-seat season tickets.