As I reported earlier today via my QuickDeals page, Sears is currently offering 12 miles per dollar for shopping through the United MileagePlus Shopping portal, and 16 miles per dollar for MileagePlus cardholders. Unfortunately, this promotion runs for just 2 days (Oct 8th and 9th). 16X is the best payout for Sears that I’ve ever seen, and 12X is second only to the one time 15X promotion they ran last year through the Southwest Rapid Rewards portal (also for just 2 days).

Here are a number of ways to get the most out of this current promotion…

Freedom, additional 5X

The Chase Freedom card is offering 5X this quarter for Amazon.com and select department store purchases. Sears is explicitly listed as one of those department stores. So, start your shopping through the MileagePlus portal, go to Sears.com, and pay for merchandise with your Freedom card. If you are also a MileagePlus cardholder, you should earn 5X Ultimate Rewards and 16X United miles.

Discover, additional 5%

The Discover card is offering 5% cash back this quarter for “online shopping.” Purchases at Sears.com should count for this bonus.

Plink, additional 6%

Regardless of which credit card you decide to pay with, if you sign up for Plink first and add Sears and Kmart to your Plink wallet, you could earn up to 6% in the form of Plink points, but to maximize this you would have to make your purchases $50 at a time. Plink points can be redeemed for gift cards such as Amazon.com, Walmart, and many others via the Tango card. See “Plinking Sears” for details.

e-Gift cards

This one is a bit risky, but it just might work. Mommy Points discovered that the Sears terms and conditions now say “Gift Cards eligible as of 10/4/13.” In many past experiments, I and others had found that purchasing physical gift cards at Sears.com through portals worked to earn points, but purchasing e-gift cards did not. It seems very likely that the new terms & conditions mean that e-gift cards are once again working! I’ll test this out, of course, but it usually takes four or five days to get confirmation of portal purchases, so we won’t know for sure in time for this promotion.

Also note that e-gift cards are sold and fulfilled by Sears, so the Freedom 4th quarter bonus should apply to Sears e-gift card purchases.

Discount e-Gift cards

Another option is to buy Sears, Kmart, or Lands End e-gift cards at a discount from gift card resellers or other means, then use those gift cards through the MileagePlus portal to double dip. See “Best options for buying merchant gift cards“.

Physical gift cards

Purchasing physical gift cards from Sears always seems to work for earning portal points, so this is a safer bet. Unfortunately, physical gift cards are sold and fulfilled by Kmart, so you most likely will not earn an additional 5X if paying with your Freedom card. Best bet is probably to buy $50 at a time with a credit card linked to Plink and with Kmart in your Plink wallet. With this approach, you’ll earn 12X to 16X United miles plus 6% back in the form of Plink points.

Also note that physical gift cards are sold and fulfilled by Kmart, so the Freedom 4th quarter bonus most likely will not apply to Sears physical gift card purchases.

Double dip

If you take a chance and go for e-gift cards, then you may receive them in time to double dip with this promotion: go through the portal once to buy e-gift cards, and then go through the portal again to use the gift cards to buy merchandise. In total, you could earn 32 United miles per dollar with this approach! That doesn’t even count any additional points you’ll get from your credit card, Plink, and Sears’ Shop Your Way Rewards!

Upgrade gift cards

If you’re not interested in Sears’ products, another option is to buy Sears’ gift cards and then upgrade them to other gift cards at Sears or Kmart. At Sears, you would have to find the secret gift card rack (please read “The mysterious case of the secret gift card rack” for details). The secret gift card rack often has $100 Visa gift cards available for $105.95 as well as a number of merchant gift cards with no fee. I’ve never had any trouble using a physical Sears gift card or a printed e-gift card to buy other gift cards at Sears.

Kmart is a different story. Kmart’s rule is that you cannot buy gift cards with gift cards. In practice, though, some cashiers allow it. Some stores are hard coded not to allow Amex, Visa, and MasterCard gift cards, though, so go for merchant gift cards instead. Maybe throw a few into your cart with a bunch of groceries just to be safe. Also note that Kmart requires a manager override to apply e-gift cards, so stick with physical gift cards if you plan to go this route!

Using gift cards

Sears gift cards can be really handy for general use. They can be used at Sears for merchandise, car maintenance, eye care, etc. They can also be used at Kmart, Lands’ End, Crafstman, Kenmore, PartsDirect, Sears Outlet, and even with My Gopher for online grocery purchases. So, if you don’t have an immediate need for Sears’ merchandise, it may be worth stocking up on gift cards to get rewards now, and then use the gift cards later.

Options for combining techniques

There are a number of ways to put together the above suggestions to maximize your earnings. Here are two examples:

Quick Quadruple dip:

If you’re willing to take a chance on e-gift cards, you could maximize earnings on Sears’ purchases as follows:

Sign up for Plink. Register the appropriate credit card and put Sears in your Plink wallet (Kmart too, just in case).

Go through the MileagePlus portal to Sears and buy e-gift cards $50 at a time (go back through the portal each time). Earn 6% back in Plink points. Earn up to 16X United miles.

Pay with your Chase Freedom card or Discover card. Earn 5X or 5%. Max $1500 in spend per quarter.

Once your gift cards arrive via email, go through the MileagePlus portal again to buy merchandise and pay with your gift cards. Of course, don’t forget to apply any coupons or other discounts that you can find. Earn up to 16X United miles and 1% or more in Sears’ rewards.

In total you could earn up to:

32 United miles per dollar

6% in Plink points

5X or 5% from your credit card

1% or more in Sears’ ShopYourWay Rewards points.

While not all of the above rewards are equal, it is convenient to add up the rewards: 32X + 6X + 5X + 1X = 44X!

Slow Quadruple dip:

A safer option is to buy physical gift cards, but then you will not receive them in time to double dip with this 16X promotion. Instead, you could order gift cards now and wait for the next decent promo. Since Sears’ has had 9X promos several times recently, let’s assume we’ll see that again:

Sign up for Plink. Register the appropriate credit card and put Kmart in your Plink wallet.

Go through the MileagePlus portal to Sears and buy physical gift cards $50 at a time (go back through the portal each time). Earn 6% back in Plink points. Earn up to 16X United miles.

Pay with your Discover card. Earn 5% (I don’t expect the Freedom 5X bonus to work here since these gift cards are processed by Kmart). Max $1500 in spend per quarter.

Once your gift cards arrive, wait for the next decent Sears’ portal promotion. Let’s assume 9X appears somewhere. Go through that portal (the one offering 9X) to buy merchandise and pay with your gift cards. Of course, don’t forget to apply any coupons or other discounts that you can find. Earn 9X miles and 1% or more in Sears’ rewards.

In total you could earn up to:

16 United miles per dollar

6% in Plink points

5% from your Discover credit card

1% or more in Sears’ ShopYourWay Rewards points.

9X from another portal.

While not all of the above rewards are equal, it is convenient to add up the rewards: 16X + 6X + 5X + 1X + 9X = 32X.

Questions and Answers

Q: How can I make sure to get the miles from this promotion? I tend to have bad luck with portals.

A: Make sure to disable ad blockers, browser toolbars, and other plug-ins before shopping as they can interfere with the portal tracking. Please see “How to ensure your portal points” for more. Also, if you plan to buy lots of gift cards, spread the risk by making several separate purchases. Make sure to go back through the portal each time. Also, buy physical gift cards rather than e-gift cards since it is unknown right now whether e-gift cards will result in portal miles.

Q: Do I have to pay with my MileagePlus credit card to get 16X?

A: Nope. You just have to be a MileagePlus cardholder. Pay with whichever card gives you the best rewards.

Q: When I put a physical gift card in my cart, it says “Sold by Kmart and Fulfilled by Kmart” so I don’t believe I’ll earn miles for this purchase.

A: It’s true that physical gift cards are processed by Kmart, but many past experiments have shown that you will still get portal miles for clicking through to Sears and buying physical gift cards.

Q: Will I earn 5X with my Freedom card this quarter if I make a purchase at Sears through the United MileagePlus Shopping portal?

A: Yes, as long as the transaction is processed by Sears, you should earn the Freedom card’s 4th quarter 5X bonus. Note that you probably will not earn this bonus for physical gift card purchases since those are processed by Kmart.

Q: How long will it take for my miles to post?

A: Most mile earning portals show pending results between 3 to 7 days after a purchase. For very large purchases (>$1,000), it often takes longer. Sometimes it can take up to 3 weeks or so for the transaction to show up in your account within a portal. It will take considerably longer for the miles to actually post to your account for use.

Q: The T&C in the promotional email differs from the one on the portal’s website. Which is correct?

A: Within the promotional email, it says: “Not eligible on gift cards, gift certificates or any other similar cash equivalents.” On the website, though, it says: “Gift Cards eligible as of 10/4/13.” My guess is that the promotional email has not been appropriately updated with the new terms. Since the website’s T&C mentions a specific and recent date, I believe that to be the updated text.

Q: Can you buy Sears gift cards online with other Sears’ gift cards?

A: No

Q: Can you use Sears’ gift cards in-store to buy other merchant gift cards?

A: Yes, it is possible, but it is not necessarily easy. See “Upgrade gift cards” above.

Q: Can you combine multiple Sears’ gift cards into one?

A: I don’t know. I’ve been meaning to try this out in-store, but haven’t had a chance to. Anyone else know?

Q: Can I use my Home Improvement gift cards to pay for items at Sears and get miles through this promotion?

A: Yes, that should work. It used to be possible to buy physical gift cards from Sears this way too, but that stopped working. You might be able to buy e-gift cards this way, though. Please let me know how it goes if you try it. Note that Sears puts a $1 hold on the card before processing it, so make sure to spend $1 less than your card’s balance.

Q: Is there anything worth buying and selling?

A: I haven’t researched this yet, so I can’t say for sure. Often, good bets are DSLR cameras where you get an additional discount if you throw in a camera lens. Also look for popular tablets or laptops that sell at a competitive price. Expect to lose some money if you do this. Hopefully, though, the value of the miles earned will far outweigh the loss of money.

Q: Are there any great sales going on at Sears right now?

A: Reader suggestions?

Q: The terms say “Not eligible on purchases made with coupon or discount codes that are not found on this site.” Is that true?

A: I’ve always received points from Sears when using coupon codes even if they were not shown in the portal, but there are no guarantees. It’s certainly safer to use the discount codes displayed in the portal.