Travel Deals

Awesome Southwest Sale – From $29 for Travel Into May!

Written by Charlie

Check out this great new Southwest sale with many city pairs starting at just $29 for one way travel! This sale runs all the way into May for great travel!

If you are looking to travel in the next few months and Southwest services those cities, definitely check out this sale! With some great city pairs starting at just $29, you may find some incredible deals!

Southwest Sale from $29 for Winter/Early Spring Travel

Link: Southwest Sale

Southwest Sale Details

  • Purchase from January 4 through January 7, 2021, 11:59 p.m. Central Time.
  • Continental U.S. and interisland Hawaii travel valid January 26 through May 26, 2021.
    • Travel continental U.S. to/from Hawaii valid January 25 through May 20, 2021.
    • Travel to/from San Juan, Puerto Rico valid January 25 through May 20, 2021.
    • International travel valid January 25 through May 20, 2021.
  • Travel from continental U.S. to Hawaii blacked out February 11-14, March 19-20, March 26-28, and April 1-3, 2021.
    • Travel to continental U.S. from Hawaii blacked out February 19-21, March 27-28, and April 2-5, 2021.

I checked some of the normal city pairs that I use to evaluate the value of Southwest sales and found that they also were running offers at just $29 (or $39) one way. This is great since the regular price on some of these city pairs is $79 or $99 one way!

January – May would normally be a nice time for travel or getting in that last ski trip of the year. Who really knows what 2021 is going to look like with travel in just a couple of months, but the good news is that, as always, you can just cancel your flights with Southwest and get the cash price back as a credit (good for use 1 year from the day you booked the tickets) or all you points back – at no charge!

It is nice to see a strong Southwest sale – if you can find a city pair that works for you, book now and change/cancel later if things aren’t looking good enough for you!

Check Your Already-Booked Reservations For Price Difference

So, now is the time to search for your tickets within this sale and see if you have a better price available now than when you had booked it. If the price has dropped, you simply select to change the flight and look at the same dates and flights again. Once you go through and confirm, you will receive a refund of the difference in miles and the cash for the taxes will be transferred for the new ticket.

In 1 Minute, You Can Have Your Points Back!

The whole process takes less than 60 seconds and you could save a lot of money or points! If you had booked your ticket in the past using cash, you will receive a refund in the form of a credit that is usable for 1 year from the time you originally booked the ticket. If you booked it with points, you will receive the points back in your account for the difference.


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About the author


Charlie has been an avid traveler and runner for many years. He has run in marathons around the world for less than it would cost to travel to the next town - all as a result of collecting and using miles and points. Over the years, he has flown hundreds of thousands of miles and collected millions of miles and points.
Now he uses this experience and knowledge to help others through Running with Miles.