Southwest Airlines regularly hosts contests and sweepstakes that you can enter to win points or free trips. They generally rotate each month, and February’s opportunity is live with the chance to win a Turks & Caicos vacation at the Blue Haven Resort.

Southwest sweepstakes have included trips to destinations all over the world from New Orleans to Paris, and they often send winners to festivals and special events. Lately, they’ve been sending flyers to the Caribbean!

How to Enter the Southwest Sweepstakes

All you have to do to enter the Southwest sweepstakes is go HERE (if you have trouble with this link, right click and choose “open link in new tab”), view the current contest and then fill out the form, which asks for your name, email, zip code and preferred airport.

You can only enter once and you must be 21 and a legal resident of the U.S. (excluding Alaska) and Washington, D.C.

Any points earned through a Southwest contest are usually bonus points, so they would NOT qualify for the points you need to earn the Southwest Companion Pass, which lets one person fly free with you for up to two years.

And now, through February 11, it’s even easier to earn the Companion Pass.  Sign up for any of the Southwest Rapid Rewards Visa personal credit cards, spend $4,000 in the first 3 months and get:

  • 30,000 points AND
  • A Southwest Companion Pass good through the end of 2019

Choose from Priority ($149 annual fee and the BEST card if you fly Southwest frequently), Premier ($99 annual fee) or Plus ($69 annual fee). I lay out the benefits/drawbacks of all three of these cards here and here is my FULL REVIEW on the Southwest Priority Visa card.

Here are the full details on this AWESOME offer.

Want someone to walk you through EXACTLY what you need to do to earn your 2019 Southwest Companion Pass — no guesswork required ;-)? Enroll in my online course, “How to Earn Your 2019 Southwest Companion Pass … Step by Step.” It comes complete with step-by-step checklists, case studies, roadmaps and everything you need to get your pass quickly and cheaply!


To apply for and review any credit cards in this post, please use the Compare Credit Cards link below. This allows me to earn a commission — at no cost to you — to pay the blogging bills so I can continue to bring you great information FREE! Thank you for your support!

Compare Credit Cards

Current Southwest Sweepstakes: Win a Vacation to Turks & Caicos

The latest Southwest sweepstakes gives you a chance to stay at the Blue Haven Resort in the beautiful Turks & Caicos islands. The package includes:

  • Round trip airfare on Southwest for two
  • Four-night double accommodations in an oceanfront suite (including a spa credit)
  • Airport and hotel transfers

Taxes and fees of at least $5.60 per one-way flight not included. You must take the trip between April 1, 2019,and February 29, 2020.

Enter to win here

The contest ends February 28, 2019 at 11:59 p.m. Central Time. Southwest will draw a winner around March 11, 2019.

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