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Southwest Big Winter Sale: Fares as Low as $49

Southwest Big Winter Sale: Fares as Low as $49

Million Mile SecretsSouthwest Big Winter Sale: Fares as Low as $49Million Mile Secrets Team

We devote thousands of hours of research to help you get Big Travel with Small Money. You support us by signing-up for credit cards through partner links which earn us a commission. Here’s our full Advertising Policy.

Time to book your winter flights.  Southwest is having a 72 hour fare sale from today until October 16, 2014, for travel between December 3, 2014, and February 11, 2015.  This is 1 of Southwest’s best sales with fares as low as $49 including tax for a 1-way flight.

Southwest Big Winter Sale Fares As Low As 49
Southwest Is Offering Flights From $49 Each Way

Note:  Like previous Southwest sales, travel on Fridays and Sundays is excluded, so you won’t save on a quick weekend getaway!  Plus, most fares are higher than $49!  And travel over December 18, 2014, to January 5, 2015 is excluded.

If you’ve already booked tickets for winter travel, check back to see if the fares have dropped for your trip.  You can always cancel and rebook at the lower price, and won’t pay a change fee.

What’s the Deal?

Link:   Southwest Big Winter Travel Sale

You can book from now until 11:59 pm (in the time zone of the city you’re traveling from) on October 16, 2014, for travel between December 3, 2014, to December 17, 2014, and January 6, 2015, to February 11, 2015.

Fares are as low as $49 1-way including taxes.  But most fares are higher.

Southwest Big Winter Sale Fares As Low As 49
You Can Fly 1-Way From San Diego to San Francisco for ~$48 Including Tax!

I LUV Southwest sales because when fares go down, the number of award points goes down, too.  That’s because the point cost of Southwest award tickets are based on the cost of the cash fare!

Southwest Big Winter Sale Fares As Low As 49
2,214 Southwest Points and $5.60 Gets You a 1-Way Ticket From San Diego to San Francisco

Southwest has a revenue-based frequent flyer program, so a fare sale means that both cash AND award bookings using points will usually cost less!

  • $49 or 2,214 points for flights up to 500 miles
  • $99 or 5,470 points for flights 501 miles to 1,000 miles
  • $129 or 7,424 points for flights 1,000 miles to 1,500 miles
  • $149 or 8,726 points for flights more than 1,501 miles

You’ll usually pay ~$81 each way from San Diego to San Francisco.  So you’ll save ~$33 each way in this case.  That’s almost enough to buy another sale ticket!

Cancel & Rebook!

Even if you’re not sure of your winter plans, you can book a ticket with this sale and cancel at a later date if plans change.  On an award booking, the points will get transferred back into your account.  And you pay NO fees!

And on paid tickets, you’ll get a credit which you can use up to 1 year after the booking was made (as long as you cancel at least 10 minutes before your flight).  You’ll never pay change fees when you change or cancel a ticket!

If you’ve already booked flights on Southwest, check to see if the fare has dropped.  You can always cancel and rebook at the lower fare without paying a fee.

Are Other Airlines Matching the Sale?

Even if you don’t fly on Southwest, other airlines may start matching Southwest’s reduced fares!

I checked Kayak for flights from San Diego to San Francisco on the same day as the previous example.  So far, the cheapest fare is on Virgin America at $49 (the same as Southwest’s regular fare).  So in this case, some airlines are matching the sale.

Southwest Big Winter Sale Fares As Low As 49
Virgin America Is Matching Southwest’s $49 Sale

I checked for a flight from Phoenix to Chicago on December 6, 2014, on Southwest.  The cheapest price is ~$128 including tax.

Southwest Big Winter Sale Fares As Low As 49
You Can Fly 1-Way on Southwest From Phoenix to Chicago for ~$128

A Kayak search found a cheaper fare on Frontier Airlines.  They charge ~$118 including tax, so you’d pay ~$10 less.

Folks who collect Frontier Airlines miles might prefer this, but remember you won’t get 2 free checked bags on Frontier Airlines like you would on Southwest.  And you have to pay a carry-on bag fee on Frontier Airlines!  

Southwest Big Winter Sale Fares As Low As 49
You Pay ~$10 Less For Your Ticket on Frontier Airlines, But You’ll Pay $25 to Carry-on Your Bag

Even if Southwest didn’t offer the lowest price, I’d still choose Southwest.  That’s because you get free checked bags and if you have the Companion Pass, your companion flies free.  So you can get Big Travel with Small Money!

Drawbacks and Limitations

Friday and Sunday travel is excluded, so you can’t travel on the weekends!

Southwest Big Winter Sale Fares As Low As 49
You Can Fly on Southwest to New York

There are a number of restrictions on these tickets.  For example:

  • Travel to Florida or Nevada is valid Sunday through Wednesday only
  • Travel from Florida or Nevada is valid Tuesday through Friday only
  • Travel between Nevada and Florida is valid on Tuesdays and Wednesdays only
  • Blackout Dates Apply:  December 18, 2014, through January 5, 2015 
  • Fares are valid on non-stop flights only

You can read the full terms and conditions on the Southwest website.

Don’t Have Enough Southwest Points?

Link:   Chase Sapphire Preferred

Link:   Chase Ink Plus

Link:   Chase Ink Bold

If you don’t have enough Southwest points, you can instantly transfer Chase Ultimate Rewards points to Southwest from your Chase Sapphire Preferred, (no longer offered) Chase Ink Bold, or Chase Ink Plus card.

Or you could sign-up for 1 of the Chase Southwest credit cards.  They’ve increased the sign-up bonus to 50,000 points, which can get you a lot of Big Travel with Small Money!

Those points count towards the 110,000 points you need to earn the Companion Pass, which is my favorite deal around for domestic travel.  With the Companion Pass, your companion flies with you for almost free on both paid and award tickets.

Southwest Big Winter Sale Fares As Low As 49
With the Southwest Companion Pass, Your Companion Flies Almost Free With You to Cancun

You’ll save a lot of money with this sale if you have the Companion Pass.  Remember that you can book flights now, but add a companion later on!

Bottom Line

If you’re planning a winter trip you could save some money with the Southwest fare sale.  You’ll need to book by October 16, 2014, and travel between December 3, 2014, to December 17, 2014, and January 6, 2015, to February 11, 2015.

Even if don’t have firm plans, you could book tickets now and change or cancel later without paying a fee.

And if you already have a flight booked, it’s worth checking to see if the fare has dropped.  You won’t pay a fee to change your ticket.  You’ll get your points back if you cancel an award ticket, or a travel credit good for 1 year on a paid ticket.

Emily and I might be able to take advantage of this sale, although we prefer to only travel on weekends.  Maybe you can plan a trip!

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Chase Sapphire Preferred® Card

Chase Sapphire Preferred® Card

  • Earn 50,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $625 toward travel when you redeem through Chase Ultimate Rewards®
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  • Get 25% more value when you redeem for travel through Chase Ultimate Rewards. For example, 50,000 points are worth $625 toward travel.
  • No blackout dates or travel restrictions - as long as there's a seat on the flight, you can book it through Chase Ultimate Rewards

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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Hi Daraius,

I presently have a southwest business card and a personal card that I got almost two years ago. My companion pass is running out at the end of this year and I want to get another. Should I cancel the other ones first and then apply for the other versions, or not cancel and just apply? What would be the timeline for doing it.

Thanks for your help!

I had a one way TPA>LGA booked for 10,940 points….I just cancelled and re-booked. The new price is 5,600 points. Thanks!