How to Get Up To Five Free SWA Round-trips with 50,000 Southwest Points

With the current Southwest credit card promotion you can earn 50,000 points.  The beauty of the Southwest program is that if you can find dirt cheap fares, your miles can keep on giving you more and more free travel.

Of course, it is always good to have a stock pile of miles with different programs and book tickets with whatever airline is offering the best value at the time of booking.  If you live in a Southwest city and are planning on traveling domestically, I suspect it will be hard to find a better redemption value than using your Southwest points.

As a result, I thought I’d share some tips on how to get the lowest fares (thus also, lowest points redemptions) with Southwest.

3 Ways to Stretch Your Southwest Points to Cover as Many Flights as Possible

1.  Install DING

About 3/4 of the way down the homepage you’ll see something that says “Sign Up For Exclusive Savings: CLICK ‘N SAVE’ DING” (as shown below).  If you click there, you can download a program called DING.


Once you’ve installed DING you can start watching for special fares from the cities you select.

A recent DING alert let me know there is a sale between Denver and Corpus Christi.  The sale is only available for flights between August 1st and 31st, but if you’re planning on traveling on those dates you’d really be able to s-t-r-et-c-h your points.  In fact, you’d be able to get 10 one way flights between DEN and Corpus Christi with your 50,000 points.


2.  Use the Lowest Fare Calendar

After entering your departure and arrival city and searching for fares, you’ll be displayed fares for the dates you’ve searched.  However, if you click on “Try our Low Fare Calendar”, you’ll be able to see which dates have the cheapest flights.


After click on the Low Fare Calendar it will display something like the calendar below.


This way when you’re planning your trip, if you have flexibility you can plan it around the cheapest travel days (typically Tuesday, Wednesday, Thursday, and Saturday).

3.  Buy a Good Price, But Always Watch for Lower Prices

One mistake some folks make with Southwest is they think that the last thing they should do is buy tickets.  However, due to Southwest’s change policy, when you buy tickets you always have the opportunity to create your own lowest fare guarantee.  Essentially, if you ever find a lower fare, you can cancel your existing itinerary and purchase the lower fare without any fees – and keep the cash or points difference.

For example, you buy a one way points flights for 10,000 points.  A few months later, they have the same flight (or a new one if you change plans) for 8,000 points.  You can buy the new 8,000 point flight with no fees, and they’ll redeposit the difference, 2,0000 points, back into your account.

One thing I didn’t feel was worthy of its own section, but I did want to mention is that you can always find the best fares online with

My theory is if you’re going to sign up for the Chase Southwest credit card to get 50,000 bonus points (expired), then you really ought to try and get 5 round-trip flights out of it instead of the posted two free flights.

Do you know of any other tips to help stretch your points or dollars when booking with Southwest?


  1. Kurtis says

    Of the two Chase cards being offered right now, the Sapphire Preferred and the Southwest card, which do feel is the better deal?
    The Sapphire Preferred seems far more versatile, yet the Southwest will likely get more domestic flights.
    I have a Sapphire Preferred and am wondering if my wife should get one to bring us a total of 100,000 UR points, or go with Southwest instead.
    Thus, diversifying our portfolio, you might say.

    • Craig says

      For domestic travel the Southwest card may be a better deal depending on the departure and arrival airports. If you want flights between two cheap Southwest cities then you’ll be able to get as more flights out of the Southwest card.
      However, like you said the advantage of the Sapphire Preferred is versatility. You can transfer them to different different airlines (like Continental or British Airways), use them at hotels (like Hyatt) or use them to book travel with the points.
      Personally I’d rather have the Sapphire Preferred but I also like the option of using the points overseas.

  2. Charles says

    I use to monitor for any price drops for my designated flights. They will send me an email whenever the price drops. They monitor all the airlines, including my favorite, Southwest. This way I can stop checking the Southwest low fare calendar. This website does it for me!

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