Travel Sweepstakes in Madison, WI: Updated 2026 List for Local Winners

Three travel-prize sweepstakes are open right now to adults in Madison, Wisconsin, and the closest deadline is October 26, 2026. A sweepstakes is a free prize drawing — no purchase necessary, and winning is a matter of chance, not merit or spending. This list includes only promotions whose sponsors publish current official rules that cover Wisconsin residents.

Two Wisconsin-reachable travel drawings closed earlier this year and are listed below so you do not waste time on them.

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

The nearest deadline: a Kenya and Tanzania safari, October 26

Chicago public broadcaster WTTW runs a 2026 "Be a Winner" Sweepstakes open only to people 18 or older who physically reside in Illinois, Indiana, Michigan or Wisconsin, which puts Madison squarely inside the eligible area. Entries must be received or postmarked by 11:59 p.m. CDT on October 26, 2026, according to WTTW's 2026 sweepstakes rules — five days from today.

The travel prize is a pair of Road Scholar tickets to the 16-day escorted "Best of Kenya & Tanzania: A Safari & Cultural Experience" tour, with airfare from a major gateway airport included and travel to be completed by November 2028. WTTW's prize list also shows a 2027 Subaru Crosstrek Hybrid as the grand prize, so entering puts you in a drawing with more than one outcome. Two details shape your odds and your planning.

Entry is capped at twenty tickets per household, plus two bonus tickets on request, so there is a ceiling on how much you can stack. And the sweepstakes' earlier Spring Early Bird travel prize — two InquisiTours "Walla Walla Deluxe Wine Touring" packages — closed to entries on June 1, 2026, leaving only the main drawing enterable.

The widest travel prize open to Madison entrants

The Ultimate RHA Getaway Sweepstakes, sponsored by Teoxane's RHA Collection, runs from 8:00 a.m. PT on August 17, 2026 through 11:59 p.m. PT on December 31, 2026.

It is open to residents of all 50 states and D.C. who are 22 or older, with no purchase necessary, per the sponsor's official rules. What makes this the broadest option is that the destination is not fixed.

The prize covers round-trip economy airfare to a destination of the winner's choosing, four nights of hotel, ground transportation, one excursion, and $1,000 for meals and incidentals. Note the age floor. Twenty-two, not eighteen, is unusual, and a Madison college student who qualifies for the WTTW drawing may not qualify for this one.

Mastercard's Priceless Surprises and its three entry windows

Mastercard's Priceless Surprises Sweepstakes for 2026 is open to legal permanent residents of the 50 states and D.C. who are 18 or older in Wisconsin. Its structure matters more than its prize description: the promotion runs as three separate entry periods, and entries do not carry over from one to the next.

That means an entry submitted in an earlier window does nothing for a later drawing. If you want a chance in each period, you enter in each period. The trip grand prize carries two restrictions worth reading before you enter.

Travel must be completed within 12 months of accepting the prize, and it must be booked through Mastercard's designated travel agency, according to Mastercard's Priceless Surprises page. A winner with a rigid schedule or a strong preference for booking their own flights should weigh that.

The Travel Wisconsin Packers promotion needs confirming first

The Wisconsin Department of Tourism promotes a Wonder-Filled Packers Sweepstakes on its state tourism site with 2026 prize games — a Packers–Bills matchup on December 13, 2026, and a game-day package covering home games through January 2027. But the promotion's own rules page still publishes the 2025 entry window of 7:00 a.m. CT October 1 to 11:59 p.m.

CT October 22, 2025. So the 2026 entry deadline is not documented on the sponsor's rules page. Confirm the current window with the Department of Tourism before you count on entering, rather than assuming the promoted games imply an open drawing.

The published rules and eligibility page also sets terms a Wisconsin entrant should know. Entrants must be 21 or older — higher than the usual 18 — and residents of Alaska, Hawaii, Florida, New York, Rhode Island and U.S. territories are excluded.

Wisconsin is not on that exclusion list. The prizes are Lambeau Field experiences and gift cards, not transportation, so a Madison winner covers the drive to Green Bay.

Closed drawings and the cost of claiming a prize

Two Wisconsin-reachable travel sweepstakes have already ended and should not be treated as active: One caveat applies broadly and is easy to overlook when a prize is described as free. PBS Wisconsin's sweepstakes rules state that winners pay their own costs to redeem, deliver or travel to claim a prize, plus applicable taxes. "No purchase necessary" describes entry, not the full cost of winning — a trip valued in the thousands can produce a real tax bill in the year you accept it.

Of the openings verifiable today, WTTW's October 26 deadline is the one that expires first, and the RHA getaway stays open through December 31, 2026.

• PBS Wisconsin's Madison-based Lucky-Go-Happy Sweepstakes 2026 — entries had to be postmarked or received by June 1, 2026, with the drawing around June 10, 2026.
• NewOrleans.com's NOLAxNOLA 2026 Staycation Sweepstakes — ran April 2 to August 27, 2026.

Frequently Asked Questions

Can a Madison resident enter a Chicago public television sweepstakes?

Yes. WTTW's 2026 rules limit entry to people 18 or older physically residing in Illinois, Indiana, Michigan or Wisconsin, so Wisconsin residency qualifies you.

Do I have to donate to enter a public broadcasting sweepstakes?

No. These are no-purchase-necessary drawings with a free entry method published in the official rules, which is what makes them lawful sweepstakes rather than raffles.

Why does one sweepstakes require age 22 and another only 18?

The sponsor sets the age floor in its own rules. Teoxane's RHA getaway requires 22 or older, WTTW requires 18, and the Travel Wisconsin Packers rules require 21.

If I enter Mastercard's first period, am I in the later drawings?

No. The 2026 promotion runs as three separate entry periods and entries do not carry over, so each period requires its own entry.