Win Trip Sweepstakes - Page 2
Found 241 total
Enter the Kal Tire Road to the Cup Contest 2026 for a chance to win an unforgettable prize package. One lucky winner and their guest could score a trip to the 2026 Stanley Cup Final, including round-trip economy flights, two nights' accommodation, and two tickets to the big game. Plus, a $500 CAD prepaid credit card is included. The total prize value is approximately $7,000 CAD. Don't miss your chance to win - enter now before the contest closes on May 9th, 2026, at 11:59 PM PT.
Win $7,000 in value – Kal Tire Road to the Cup Contest 2026 - Enter Now
Enter the iHeartRadio VIP at New Orleans Jazz Festival 2026 Sweepstakes for a chance to win an unforgettable trip for two to the 2026 New Orleans Jazz & Heritage Festival. The grand prize package, valued at $4,700, includes a $1,200 prepaid gift card for travel, a 5-night hotel stay in New Orleans, and two Grand Marshal VIP Passes for the festival's first weekend. Don't miss out on this exciting opportunity to experience the best of jazz in the Big Easy - enter to win by April 12, 2026, at 11:59:59 p.m. ET for your free chance to claim this amazing prize.
Win $4,700 in value – iHeartRadio VIP at New Orleans Jazz Festival 2026 Sweepstakes - Enter Now
Get ready to win big with Hawaiian Host Inc.'s Hawaiian Host Share Your Aloha Sweepstakes. To celebrate the launch of their new AlohaMacs boxes, they're partnering with Hawaiian Airlines and Mana Up to give away an amazing prize. Enter to win two roundtrip tickets to any destination Hawaiian or Alaska Airlines flies within Hawai‘i and North/Central America, plus Hawaiian Host and Mana Up prize packs, valued at $3,750. To enter, click the link in their bio or scan a QR code at your local Hawai‘i retailer by May 15, 2026. No purchase necessary, open to legal U.S. residents (excluding RI) 18+, visit https://hawaiianhost.com/pages/win-a-trip-official-rules for rules. Sponsored by Hawaiian Host Group, enter now for a free chance to win with Hawaiian Host Inc.
Win $3,750 in value – Hawaiian Host Share Your Aloha Sweepstakes - Enter Now
Get ready for Stagecoach with HEYDUDE's HeyDude Trip Giveaway! Enter to win a free trip to the desert, including round trip flights, a weekend stay, and 2 General Admission wristbands for you and a friend. To enter, like this post, follow @HEYDUDEcountry on x and @heydude on Instagram, and tag your festival buddy. Boost your chances with an extra entry by posting about us on your story. Open to U.S. residents only, ending 4/7/26 at 11:59PM EST. Winners will be notified via DM from @heydude. Check the link in bio for official terms. HEYDUDE is giving you the chance to win big - enter the HeyDude Trip Giveaway now!
Win $1,000 in value – HeyDude Trip Giveaway - Enter Now
Enter the iHeartRadio Rolling Loud 2026 Sweepstakes for a chance to win an epic prize package. One lucky winner will receive a trip for two to weekend two of the 2026 New Orleans Jazz Fest, complete with round-trip air transportation, four nights of hotel accommodations, and two VIP weekend 3-day tickets to Rolling Loud USA. The approximate retail value of this amazing prize is $3,900. Don't miss out on this incredible opportunity to win big with iHeartRadio.
Win $3,900 in value – iHeartRadio Rolling Loud 2026 Sweepstakes - Enter Now
Enter the iHeartRadio Three Days Grace National Flyaway Sweepstakes for a chance to win an unforgettable trip for two to see Three Days Grace live in LA on November 22, 2026. The prize package, valued at $2,500, includes round-trip airfare, two nights of hotel accommodations, and two tickets to the show, plus on-stage access. To be eligible, winners must follow strict terms and conditions, including providing a Ticketmaster email address, arriving by 8:00 p.m., and adhering to safety protocols and dress code rules. Winners will be featured on stage and may be filmed or recorded. Enter to win this exclusive experience, courtesy of iHeartRadio.
Win $2,500 in value – iHeartRadio Three Days Grace National Flyaway Sweepstakes - Enter Now
Enter the Wedding Vibe VIB Very Important Bride Paris Honeymoon Giveaway for a chance to win an unforgettable trip for two to Paris, France. This incredible prize includes a romantic dinner at the Eiffel Tower, wine tasting, and a luxury swag bag for the bride-to-be. One lucky winner will be selected to live their honeymoon dream in the city of love and lights. Enter to win this amazing giveaway by 04/27/2026 for your chance to take home this prized getaway.
Win $1,000 in value – Wedding Vibe VIB Very Important Bride Paris Honeymoon Giveaway - Enter Now
Enter the Classic Anniversary Sweepstakes, a year-long celebration by Classic Vacations, where travel advisors can win exciting prizes to Europe, The Islands of Tahiti, and Costa Rica. To participate, advisors must be 18+ years old, legal residents of the 50 US states or DC, and have an active account with Classic Vacations. Employees of Classic Vacations and their families are not eligible. The sweepstakes features three Destination Spotlights, each with a quiz, and advisors can earn entries through eligible bookings or by mailing a handwritten entry ( AMOE in rules ). The Europe Spotlight Period runs from January 6 to May 31, 2026, while the Tahiti & Costa Rica Spotlight Period is from June 1 to September 30, 2026. Nine prizes will be awarded, including trips to Rome, Florence, Venice, Mykonos, Santorini, and more. Travel must be completed by December 15, 2027, and is subject to availability and blackout dates. Enter now for a chance to win with Classic Vacations.
Win $270,000 in value – Classic Anniversary Sweepstakes - Enter Now
Enter to win the Ultimate Luxury Family Escape to Salterra Resort & Spa in South Caicos! Sweepstakes for a chance to claim an incredible grand prize valued at $4999. This amazing prize package includes a four-night stay in a Two Bedroom Suite, daily breakfast for four, airport transportation, and a thrilling Family Excursion to Caicos Bank or Northern Cay Kayaking trip. Additional prizes feature a $350 Korres Gift card and a $250 Aurate Gift card. Don't miss your opportunity to win - the sweepstakes ends on 4/30/2026 at 11:59 pm EDT.
Enter to win the Tackle Up Ultimate Fishing Getaway With Smoker Sportfishing Giveaway for a chance to reel in an incredible $4,000 grand prize. This ultimate fishing package includes an Outer Banks Offshore Charter Fishing Trip for you and 5 friends, a $300 Tackle Up Gift Card, a $500 Grudens Gear Bundle, and up to $500 reimbursement for an OBX Airbnb stay. Don't miss your chance to win this amazing prize - enter now before the sweepstakes ends on May 31, 2026, at 11:59 PM EST with Smoker Sportfishing.
