How to Win 1 of 50 Walt Disney World Vacation Packages

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What do Walt Disney World® Resort and Southwest® Airlines have in common this year?


They’re both celebrating a ✨magical✨ 50th anniversary!

And to commemorate, they’re teaming up for 50 Days of Giveaways as well as a co-branded aircraft that guests can fly in, featuring artwork exclusively made for this celebration. Let’s go over the details on how you can enter and, hopefully, win!

Win a Walt Disney World® Resort Vacation Package

The giveaways have already started so from now until November 16, 2021, enter daily on the  Southwest® contest page to try and win one of 50 Walt Disney World® vacation packages which include:

  • Round trip air travel to Orlando, FL on Southwest®
  • Lodging for 4 nights
  • Theme Park tickets
  • $200 Disney Gift Card

They’re giving away one vacation package a day so enter every day to test your luck! The 50 winners will each get to bring 3 guests as well making it perfect for family and friends.

How to Get a Bonus Entry Each Day

After you submit your entry for the day, there is a blue Twitter “share now” button that appears.

Click on that and you’ll get a BONUS entry each day that can help your chances to win one of the Walt Disney World® Resort packages!

Special Sips & Bites Throughout the Resort

Disney Parks Blog

It wouldn’t be a celebration without special dining options and all 4 theme parks at the resort (along with Disney Springs and hotels) have new menu items.

If you win one of the packages, you’ll have a chance to try as much as you can! You can also view the full menus via the My Disney Experience mobile app.

Earn Money For Your Own WDW Vacation

While you enter daily for your chance to win, why not earn some extra money on the side to fund your own vacation?

We chatted with Brittany, who earned over $700 for her family’s Disney Trip using a free app, called Swagbucks. Learn how you can get started too and who knows, you may earn extra spending money to use on your vacation! ✨

Good luck!