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Flights From $49 With Southwest’s Winter Sale

Written by Charlie

Advertiser Disclosure

Here comes the winter sales! Southwest has opened up their fare sale today and it is available to book until October 16th @ 11:59PM (in the originating city). There are some great values to be had here! Plus, since it is Southwest and their revenue-based award program, you can also book these tickets with your points for an equally great savings. Sale fares range from $49 to $149 (one-way prices).

Southwest Winter Sale

Southwest Sale

Booking Southwest Fares

With only two days to book, it might seem like it may be rushed for your planning purposes. However, do not let that bother you. Southwest has the friendliest of cancelation policies and you can cancel a ticket for no fee up until 10 minutes of departure! The same is true whether it is a paid ticket or reward ticket. So, you can book anything now and, if you later find it inconvenient, you can either change the ticket at no charge or cancel it. Just remember, if you change it, you may need to pay a difference in fare. Also, if you cancel a paid ticket, you will receive Southwest credit towards a future flight.

The valid dates are:

  • Purchase from October 14 through October 16, 2014, 11:59 p.m. for the respective time zone of the originating city.
  • Travel December 3 through December 17, 2014 and January 6 though February 11, 2015. Travel to/from San Juan, Puerto Rico is valid December 3 through December 11, 2014 and January 13 through February 11, 2015.
  • Travel is valid every day except Fridays and Sundays. Travel to Florida or Nevada is valid Sunday through Wednesday only. Additionally, travel from Florida or Nevada is valid Tuesday through Friday only. Travel between Nevada and Florida is valid on Tuesdays and Wednesdays only.
Southwest

An example of the fare calendar on Rochester to Baltimore flights (the award price is 2,200 points)

Southwest

An example roundtrip with points during this sale – roundtrip for only 4,400 points!

Companion Pass

If you have the Companion Pass from Southwest, you can book a seat now and your companion now or wait until later to book your companion. As long as there is a seat available, you can book your companion on that seat. Just be warned – if your companion pass expires this year, you will be unable to use it for any of these fares next year. It does not matter that you have booked the award this year – the companion pass will only allow the companion to fly for as long as it is valid.

Getting the Points

Chase’s Ultimate Reward points transfer to Southwest at a 1:1 ratio, so if you do not currently have Southwest Rapid Reward points, that is the only way to get them before the sale ends. For future purposes, you can get Southwest points incredibly easy since there are four separate Southwest cards that have offers of 50,000 points quite often (one is currently at 50,000).

Then, of course, any Ultimate Reward earning card will have points that can transfer to Southwest. For anyone that travels domestically, that is certainly the best way to get the most value from your Ultimate Reward points.

Application Link – Southwest Premier Credit Card – 50,000 points after spending $2,000 in 3 months

Application Link – Chase Sapphire Preferred – 40,000 points after spending $3,000 in 30 months

Application Link – Chase Ink Plus – Limited-time Offer – 70,000 points after spending $5,000 in 3 months

Application Link – Chase Ink Bold – 50,000 points after spending $5,000 in 3 months

The information for the Southwest Premier card and Chase Ink Bold has been collected independently by Running with Miles. The card details on this page have not been reviewed or provided by the card issuer

Here are the details about the sale (to see the whole list of terms, click here):

  • Purchase from October 14 through October 16, 2014, 11:59 p.m. for the respective time zone of the originating city.
  • Travel December 3 through December 17, 2014 and January 6 though February 11, 2015. Travel to/from San Juan, Puerto Rico is valid December 3 through December 11, 2014 and January 13 through February 11, 2015.
  • Travel is valid every day except Fridays and Sundays. Travel to Florida or Nevada is valid Sunday through Wednesday only. Additionally, travel from Florida or Nevada is valid Tuesday through Friday only. Travel between Nevada and Florida is valid on Tuesdays and Wednesdays only.
  • Some flights operated by AirTran® Airways.
  • Fares valid on nonstop service only.
  • Displayed prices include all U.S. and international government taxes and fees.
  • Points bookings do not include September 11th Security Fee of $5.60 per one-way flight.
  • Points bookings do not include any additional international government taxes and fees.
  • Seats and days are limited. Fares may vary by destination, flight, and day of week and won’t be available on some flights that operate during very busy travel times and holiday periods.
  • Travel is available for one-way Wanna Get Away® Fares.
  • Fares may be combined with other Southwest Airlines® combinable fares. If combining with other fares, the most restrictive fare’s rules apply.

Editorial Note - Opinions expressed here are author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

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About the author

Charlie

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.

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