Sears 15X: Free Southwest Companion Pass


Today and tomorrow, the Southwest Airlines shopping portal (Rapid Rewards Shopping) is offering 15 points per dollar when shopping at Sears. In the post “Sears 15X: Leveraging the deal” I showed a number of ways to capitalize on this promotion. In this post I’ll show step by step how to get a Southwest Companion pass for free!  The trick shown here involves buying and selling gift cards.  It is also possible to do this by buying and selling merchandise, but that will be left for another post…


Southwest has a fantastic program in which a designated companion can fly free on all flights you take. To qualify for a companion pass, you must earn 110,000 points within a calendar year. Once you qualify, you designate a companion, and that person then can fly free anywhere you go on Southwest for the rest of that calendar year and the next calendar year. You may change your companion up to 3 times during the validity period of the pass. Full details of the pass can be found here: rapid_rewards_program_terms_and_conditions_faq.

Million Mile Secrets has written about how to earn a Companion Pass through credit card sign-ups. However, if you are already maxed out on Chase sign-ups (who isn’t?), don’t want to blow your valuable Chase sign-ups on Southwest credit cards, or have other reasons not to sign-up, then this 15X deal may be the way to go.

Step 1: Calculate how many points you need

To earn the pass, you need to earn 110,000 points in a calendar year.  Check to see how many you’ve earned so far this year and calculate the difference needed to get to 110,000.  Personally, I’ve earned 0 points so I would need the full 110,000.

Step 2: Calculate how much you’ll have to spend at Sears

Divide the number of points needed by 15 in order to figure out how much you need to spend.  Example:

110,000 points needed / 15 = $7333.34 needed to spend

If you plan to use a Southwest Airlines points earning credit card for these purchases, then divide by 16 instead of 15.

Step 3: Log into the Rapid Rewards Shopping portal

If you don’t already have a Southwest Airlines Rapid Rewards account you’ll need to sign up for one first.  Then go to

Step 4: Click through to Sears


Step 5: Buy gift cards

Take the result of your calculation in step 2 and buy that amount of gift cards.  Buy physical cards (card type “mail”), not e-cards because the physical ones are easier to sell.  If you need all 110,000 points, then you would need to buy $7335 worth of gift cards.  Don’t do this unless you have plenty of available credit and the ability to pay off your credit card bill in full.

Step 6: Sell gift cards

Once you receive your cards in the mail, sell them as follows:

  1. Log into TopCashBack and click through to Plastic Jungle.
  2. Sell your gift cards to Plastic Jungle

Currently, Plastic Jungle offers 83% cash back for Sears gift cards and Plastic Jungle adds another 3.32% (4% of 83%).  If you sell $7335 worth of gift cards you should get back $6088.05 from Plastic Jungle and $244.19 from TopCashBack.  In my experience Plastic Jungle pays very quickly.  TopCashBack takes longer because they can’t pay until they get paid themselves by the merchant.  In total you should get $6332 back.  At this point you would be out $1003.

Step 7: Wait for your points to post

Once your points post, you should have enough points for a Companion Pass!

Step 8: Liquidate your points (optional)

First, consider keeping the points so that you and your companion can travel for free for a long time!  If you really need your $1003 back, though, then do the following:

  1. Log into your Southwest account and go to “Redeem Points”.
  2. Find the option to redeem points for gift cards.
  3. Buy Walmart gift cards with your points.
  4. Once you get the Walmart gift cards, sell them in the same manner described in step 6.

110,000 points would get you 22 $50 Walmart gift cards. Plastic Jungle will currently buy them for 92% of their value. By going through TopCashBack, you will get another 3.68% of their value for a total of 95.68%. In other words, 110,000 points should translate into $1052.48 cash back.

Add it up

If all of the above works, here is what you will get for the effort (assuming you went for the full 110,000 points):

  • One Southwest Companion Pass
  • About $50 in profit
  • $7335 in credit card spend.  If you’re working on meeting minimum spend requirements or liquidating gift cards, this could be a huge win.  At the very least this means 7335 points or miles depending on what credit card you use.

Cautions and Risks

Everything written in this post carries some risks. Don’t do this unless you are prepared for the worst. Here are a few obvious risks:

  1. You shop through the portal, but don’t get any points. To minimize the chance of this, please see my post “How to ensure your portal points”.
  2. Purchases of gift cards don’t receive points. I think this is unlikely, but it is possible since I’ve never tested this portal.
  3. Southwest may change the redemption rates for gift cards.
  4. Plastic Jungle may reduce the payout amount for Sears or Walmart cards, or TopCashBack may reduce the cash back amount.
  5. Gift cards may get lost in the mail or improperly cataloged by Plastic Jungle.


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