Book Discounted Southwest Flights Through May 2019 Starting at $41 One-Way (Ends Soon)

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Book Discounted Southwest Flights Through May 2019 Starting at $41 One-Way (Ends Soon)

JasonBook Discounted Southwest Flights Through May 2019 Starting at $41 One-Way (Ends Soon)Million Mile Secrets Team

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Southwest has frequent award sales & promotions, so if you don’t want to miss out on the next one subscribe to our newsletter and we’ll deliver these sales (and other travel deals) straight to your inbox. 

If you’re looking to book a trip for 2019, Southwest has the sale for you!  You’ll need to book by December 13, 2018, but the discounts apply to flights through May 22, 2019.

And if you’ve already booked any Southwest flights, this is also a great time to check and see if the price dropped because you’ll be able to change your flight (and save) for free!

Plus, folks with the Southwest Companion Pass could fly even more cheaply.  Because, with the Companion Pass, your companion flies with you for just the cost of taxes & fees on both paid and award tickets!

Now is the perfect time to earn a Southwest Companion Pass because there are increased offers on all 4 Chase Southwest credit cards!  And if you earn the sign-up bonus on the Southwest Rapid Rewards® Premier Business Credit Card and one of the personal cards in the same calendar year, you’ll earn yourself a Southwest Companion Pass!

Cheap Southwest Flights Could Have You on a Beach in San Diego in No Time!

Southwest Sale

End date:   December 13, 2018, at 11:59 pm local time in originating city

Travel dates:   Continental US travel valid December 18, 2018, to May 22, 2019.  Travel to/from San Juan, Puerto Rico valid January 14 through February 28, 2019, and April 23 through May 16, 2019.  International travel valid January 8 through March 6, 2019, and April 23 through May 16, 2019.

Terms & restrictions:   Continental US travel blacked out December 21 to 23, December 26 to 27, and December 29 to 30, 2018.  14-day advance purchase for domestic flights.

Sample one-way routes include:

  • Atlanta to Boston for $72
  • Atlanta to Nashville for $67
  • Austin to Orlando for $97
  • Long Beach to Las Vegas for $41
  • New York to Chicago for $91
  • San Diego to Sacramento or San Jose (CA) for $49
  • and more!

The full sale details and other discounted routes can be found here.

One nice thing about a Southwest sale is you can also book Southwest award tickets with fewer Southwest points because the price of an award flight is tied to the cash price.  During this particular sale, you can book one-way award seats for as few as 1,943 Southwest points (+ $5.60 in fees)!

There are lots of other benefits to flying Southwest, too.  Like their generous change and cancellation policy.  And the fact that every passenger gets 2 free checked bags!  That alone is a savings of ~$30 per bag compared to other airlines.

You can also transfer Chase Ultimate Rewards points to Southwest at a 1:1 ratio.  But just remember that those transfers won’t count toward earning a Southwest Companion Pass.

Do you plan on taking advantage of any of these discounted flights?

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Southwest Rapid Rewards® Priority Credit Card

Southwest Rapid Rewards® Priority Credit Card

  • Earn Companion Pass and 30,000 points after you spend $4,000 on purchases in the first 3 months. Offer ends 2/11/19. Companion Pass is promotional and will be valid through 12/31/19.
  • Every time you fly, they fly free of airline charges* for the rest of 2019. *Does not include taxes and fees from $5.60 one-way
  • 7,500 bonus points after your Cardmember anniversary.
  • $75 Southwest® travel credit each year.
  • 4 upgraded boardings per year when available.
  • 20% back on inflight purchases made with your Southwest Rapid Rewards® Priority Credit Card.
  • 2 points per $1 spent on Southwest® purchases and Rapid Rewards® hotel and car rental partner purchases.
  • No foreign transaction fees.

More Info

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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I was wondering how can you obtain the southwest business if you do not have a business. How can you qualify for the companion pass? Can you apply for 2 regular SW cards?

You pretty much need a business in order to get the Companion Pass. If you sell something on eBay, you have a business.