Travel Sweepstakes in Pittsburgh, PA: Updated 2026 List for Local Winners
Photo: Leah Newhouse / Pexels
Pittsburgh readers can still enter four trip drawings, including Super Bowl, Steelers, cruise and L.A. prizes.
Pittsburgh, PA residents have four open travel sweepstakes to consider in early October 2026. The list includes a Super Bowl plus Disneyland trip, Pennsylvania Lottery Los Angeles trips, a Steelers road-game trip and a Caribbean cruise. A travel sweepstakes is a chance-to-win promotion where selected entrants win a trip package.
Each prize below is a chance, not a certain benefit, and each has its own entry dates and limits.
Verification note: Program terms and availability can change. This page was checked against linked sources on October 05, 2026.
Which Super Bowl and cruise trips are open?
ESPN's "We're Going to the Super Bowl" sweepstakes accepts entries September 8 through December 31, 2026. One winner and three guests receive four Super Bowl LXI tickets for February 14, 2027 at SoFi Stadium plus a three-night Disneyland Resort stay and 3-Day Park Hoppers, according to the ESPN Press Room announcement. Expedia Cruises "Win a Dream Vacation 2026" accepts entries October 1-31, 2026.
First prize is a 7-night Caribbean cruise for two in an outside stateroom with meals and activities plus roundtrip economy airfare from the major gateway nearest the winner, according to the Expedia Cruises contest rules. Pittsburgh entrants use the same national entry periods as other U.S. entrants.
Check the entry form for age, location and entry-frequency limits before submitting.
What Pennsylvania Lottery trips can you enter?
Pennsylvania Lottery VIP Players Club members can submit non-winning GAME SHOW EXPERIENCE Scratch-Offs into the GAME SHOW EXPERIENCE Second-Chance Drawing by 11:59:59 p.m. ET January 14, 2027. The drawing offers one of 47 trip prize packages, according to the Pennsylvania Lottery page.
This path requires club membership and an eligible non-winning ticket. It is separate from buying a ticket for a cash prize.
- Use only a non-winning GAME SHOW EXPERIENCE Scratch-Off
- Submit through a VIP Players Club account
- Submit before the January 14 deadline
What does the Steelers road-game trip include?
The Miller Lite Football 2026 STEELERS keyword promotion offers one grand-prize trip for a winner plus three guests to a 2027/28 Steelers road game. The package includes coach airfare for four, two nights hotel, four game tickets, $500 spending money and beer for a year, according to the sponsor rules for the Steelers promotion. The trip centers on four travelers attending the same game.
The winner must follow the keyword entry instructions and travel on the dates set for the selected road game.
Which Pittsburgh offers are no longer available?
VisitPITTSBURGH's 2026 Insider's Guide launch sweepstakes offered four customizable Pittsburgh getaways with a 4-day/3-night stay, roundtrip airfare for two, attraction tickets and $500. Entries ran only January 20-29, 2026, so Pittsburgh readers can no longer enter it. Pittsburgh stations WORD 101.5 FM and The Answer PGH cancelled the Italy Unfiltered Dream Vacation for two and the related September 2026 group tour.
No prize was awarded because of overseas travel uncertainty, so remove the Italy trip from your entry list.