Travel Deals

New Southwest Winter Sale from $39 – Save on New or Existing Travel

Written by Charlie

Take a look at this new Southwest winter sale, with tickets starting at just $39 for one way travel. There are plenty of good reasons to book with Southwest now – saving on new or existing reservations is one of them!

If you are wanting to get out and travel a bit to take a break or see family, Southwest is running a winter sale starting adjust $39 one way. Here are the details.

Southwest Winter Sale from $39

Link: Southwest Winter Sale

Southwest Winter Sale Details:

  • Purchase from October 20 through October 22, 2020, 11:59 p.m. Central Time.
  • Continental U.S. travel valid December 1, 2020, through March 4, 2021.
    • Travel Continental U.S. to/from Hawaii valid November 12, 2020, through April 8, 2021.
    • Interisland Hawaii travel valid November 12, 2020, through April 8, 2021.
    • Travel to/from San Juan, Puerto Rico valid November 12 through December 3, 2020, and January 11 through March 4, 2021.
    • International travel valid November 12 through December 9, 2020, and January 11 through March 4, 2021.
  • Continental U.S. travel blacked out December 18-19, December 23, December 26-27, 2020, and January 2-3, 2021.
    • Travel from continental U.S. to Hawaii blacked out November 19-22, December 17-27, 2020; February 11-14, March 19-20, March 26-28, & April 1-3.
    • Travel to continental U.S. from Hawaii blacked out December 26, 2020 to January 4, 2021, February 19-21, March 27-28, April 2-5, 2021

This is the time of year when there are those blackout dates on sales and this year is no different – and that is a good thing. This shows that Southwest feels comfortable charging higher rates due to travel demand being there. Also, keep in mind that Southwest is blocking middle seats through November 30.

Why Booking With Southwest is Great Right Now

Southwest is already the only US airline that gives every passenger 2 bags for free. They are also the only airline that has freely given refunds (to travel credit when booked with cash) or points back if you decide not to take a trip.

But, they also let you exchange your travel credit into points (which won’t expire the way the travel credit will) up through December 15. They also are blocking all middle seats through November 30. And, it is far easier to get refunds from them than it is other US airlines (and definitely easier than with international airlines).

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.