Earn Extra Miles and Cash Back with Holiday Shopping Portal Bonuses – and How to Maximize Them with Gift Card Purchases

Last Friday, many airline shopping portals, as well as the cashback UPromise portal, came out with new November holiday bonuses. Several of these look to be very valuable. Unfortunately, when the offers were released, we were scrambling to get out the door for a trip and weren’t in a position to get the offers published before we left. We also wanted to have time to talk about how the offers might be maximized with gift card purchases.
They’re too good not to cover at all, though – so, without further delay or ado, let’s explore the offers and potential strategies:
Alaska
The Alaska Mileage Plan shopping portal has the following bonus offer, from now through November 21, 2019:

- 300 bonus miles when you spend $150 (2x extra miles)
- 750 bonus miles when you spend $300 (2.5x extra miles)
- 1,500 bonus miles when you spend $500 (3x extra miles)
At our baseline value of 1.5 cents per Alaska mile, this promotion gives you an opportunity to earn up to an extra 4.5% in points rebates by going through the Alaska portal and spending exactly $500.
American
The American AAdvantage shopping portal has the following bonus offer, from now through November 21, 2019:

- 500 bonus miles when you spend $150 (3.3x extra miles)
- 1,500 bonus miles when you spend $600 (2.5x extra miles)
- 3,500 bonus miles when you spend $1,200 (2.9x extra miles)
At our baseline value of 1.25 cents per AA mile, this promotion gives you the opportunity to earn up to an extra 3.6% in points rebates by going through the AA portal and spending exactly $1,200.
Delta

The Delta SkyMiles shopping portal has the following bonus offer, from now through November 14, 2019 (note that the Delta offer ends 1 week earlier than the other airline portal offers discussed in this article):
- 500 bonus miles when you spend $150 (3.3x extra miles)
- 1,000 bonus miles when you spend $300 (3.3x extra miles)
At our baseline value of 1.2 cents per Delta mile, this promotion gives you the opportunity to earn up to an extra 4% in points rebates by going through the Delta portal and spending exactly $300.
Southwest
The Southwest Rapid Rewards shopping portal has the following bonus offer, from now through November 21, 2019:

- 500 bonus points when you spend $150 (3.3x extra points)
- 1,000 bonus points when you spend $500 (2x extra points)
- 3,000 bonus points when you spend $1,000 (3x extra points)
At our baseline value of 1.3 cents per Rapid Rewards point, this promotion gives you the opportunity to earn up to an extra 3.9% in points rebates by going through the Southwest portal and spending exactly $1,000.
United
The United MileagePlus shopping portal has the following bonus offer, from now through November 21, 2019:

- 500 bonus miles when you spend $150 (3.3x extra miles)
- 2,500 bonus miles when you spend $750 (3.3x extra miles)
- 5,000 bonus miles when you spend $1,500 (3.3x extra miles)
At our baseline value of 1.4 cents per United mile, this promotion gives you the opportunity to earn up to an extra 4.6% in points rebates by going through the United portal and spending exactly $1,500.
UPromise

UPromise, of course, is a cash back shopping portal rather than a mileage-earning portal. UPromise has a bonus offer that’s slightly different than the others, in that it has only 2 tiers (in addition to being cash back):
- $10 bonus cash back when you spend $250 (extra 4% cash back)
- $100 bonus cash back when you spend $1,250 (extra 8% cash back)
The UPromise bonus offer ends on November 10, 2019, several days earlier than the other bonus offers expire.
With the possibility of earning an extra 8% cash back, in addition to your regular portal earnings on UPromise, this is potentially an absolutely outstanding deal.
Strategy Considerations for All Offers
Note that all of these offers are in addition to the normal miles-earning or cash back for each merchant on the various portals. Many individual merchants are also running increased miles-earning or cash back offers as we enter the holiday shopping season, so there are opportunities to stack those increased offers with the portal bonuses to earn even more miles for your travels or cash back for your wallet!
For pointers on using shopping portals in general, see our Resource article:
Using Gift Card Purchases to Maximize These Offers
Being a lawyer, I can’t help but start this section with a disclaimer: The official terms and conditions of these bonus offers say that purchases of gift cards are not “qualifying purchases” for purposes of the bonus offer. Here is the exact language from the terms and conditions on the AAdvantage shopping portal (all of these programs run on the same back end, so all of the terms and conditions are similar, if not identical in all pertinent aspects):

For that reason, we caution you that if you try to use gift card purchases to capture these portal bonuses, you do so at your own risk.
That said, though, despite the official terms and conditions, we have successfully used purchases of Visa & Mastercard gift cards from GiftCards.com to earn similar bonuses on the Alaska, AA and United shopping portals. Here are links to articles we published about using the Alaska and AA portals:
- Middle Age Miles: MS DPs – Episode 9 – $500 VGC from GiftCards.com (August 13, 2019) (AA shopping portal)
- Middle Age Miles: MS DPs – Episode 10 – $500 MCGC from GiftCards.com (August 20, 2019) (AS shopping portal)
We have not tested whether purchases of GCs from GiftCards.com through the UPromise portal would successfully trigger a bonus. We’re guardedly optimistic given our success with the airline portals and the fact that UPromise operates on the same back end. And clearly, GC purchases on GiftCards.com receive the “regular” portal payouts on UPromise since GiftCards.com is on the UPromise portal and the only thing they sell is gift cards. Still, we caution that the UPromise portal bonus terms and conditions contain the same language as we saw on the AA eshopping site that excludes gift cards:

Purchases from GiftCards.com
GiftCards.com participates in 4 of the airline portals running these current bonus offers (all of them except Delta), as well as UPromise.com. Here is today’s listing from Cashback Monitor of the earning rates on the airline portals for purchases from GiftCards.com:

On UPromise.com, purchases from GiftCards.com earn 1% cash back:

Gift card purchases from GiftCards.com incur two different types of fees – purchasing fees and shipping fees. The amount of the purchasing fee depends on the value of the card purchased, as follows:

Shipping costs are as follows:

Although GC.com lists the same 5-9 business days for expected delivery of both Standard Mail and Trackable Mail, our experience has been that Trackable Mail purchases typically arrive several days more quickly than Standard Mail. That, plus the fact that the shipment is actually trackable, gives us a strong preference for using Trackable Mail whenever feasible.
Evaluating the Deals
Let’s take a look at several of these portal deals, using GC purchases through GC.com. To do so, we’re going to have to make a few assumptions in order to evaluate the profitability of the deals. We’re going to assume that:
- Purchases will be made with a credit card that earns 2.5% back in the form of rewards. The most straightforward example would be a Citi Double Cash card, converting the rewards to ThankYou Points (TYPs) at our baseline value of 1.25 cents per TYP.
- [Note, though, that as of 11/1/19, new terms & conditions went into effect on the Double Cash card that contain some anti-GC language – see this article from Doctor of Credit for more details.]
- You can liquidate the cards for a 2% fee.
- [No doubt, many can liquidate for less than this.]
- Our baseline values of the various mileage currencies apply
- 1.5 cents per mile for Alaska
- 1.25 cents per mile for American
- 1.4 cents per mile for United
- You can buy either Visa gift cards (VGCs) or Mastercard gift cards (MCGCs), whichever is easier for you to liquidate
In practice, we’ll probably use our Barclays AA Aviator Silver card for this spend. We’ll only earn 1x AA mile per dollar, but we still have a few thousand dollars that we need to spend to reach thresholds that will give us enough EQMs and EQDs to re-qualify for Executive Platinum status.
It’s also worth pointing out that we don’t know of any cards that earn in a bonus category for spend at GiftCards.com. So, you’ll want to use whatever card you have that (a) earns you the most on everyday spend; or (b) helps you hit a big-spend threshold for an extra bonus; or (c) has a sign-up or upgrade bonus that you’re working on (but probably not an Amex card in this instance).
Using these assumptions, let’s do the math on a few of these deals:
- Alaska – Buy $500 VGC/MCGC
- Costs = $18.75
- $6.95 purchase fee
- $1.99 shipping fee
- $9.81 to liquidate ($500 – ($500/1.02))
- Rewards = $39.01
- 253 AS miles at 0.5x (*1.5 cpm = $3.79)
- 1,500 AS miles for the bonus (*1.5 cpm = $22.50)
- $12.72 in credit card rewards (2.5% * $508.94)
- Profit = $20.26
- Costs = $18.75
- American – Buy $1,200 VGC/MCGC
- Costs = $50.34
- $18.85 in purchase fees ($6.95 + $6.95 + $4.95)
- $7.96 shipping fee (pay a little more for Trackable Mail)
- $23.53 to liquidate ($1,200 – ($1,200/1.02))
- Rewards = $89.46
- 1,219 AA miles at 1x (*1.25 cpm = $15.24)
- 3,500 AA miles for the bonus (*1.25 cpm = $43.75)
- $30.47 in credit card rewards (2.5% * $1,226.81)
- Profit = $39.12
- Costs = $50.34
- United – Buy $1,500 VGC/MCGC
- Costs = $58.24
- $20.85 in purchase fees (3 * $6.95)
- $7.96 shipping fee (pay a little more for Trackable Mail)
- $29.43 to liquidate ($1,500 = ($1,500/1.02))
- Rewards = $118.66
- 760 UA miles at 0.5x (assuming no UA card) (*1.4 cpm = $10.64)
- 5,000 UA miles for the bonus (*1.4 cpm = $70.00)
- $38.02 in credit card rewards (2.5% * $1,528.81)
- Profit = $60.42
- Costs = $58.24
- UPromise – Buy $1,500 VGC/MCGC (buying more than $1,250 as the extra $250 should be profitable)
- Costs = $58.24 (same as the United example above)
- Rewards = $153.23 (assuming that the bonus tracks on these GC purchases!)
- $15.21 on regular 1% portal earning rate at GC.com
- $100.00 for the bonus
- $38.02 in credit card rewards (2.5% * $1,528.81)
- Profit = $94.99 (and this is mostly in the form of cash!)
As you can see, these have the potential to be useful, profitable deals, assuming that you can use the miles (and everyone can use the cash back!). Numbers on the Southwest deal would be similar. This strategy won’t work on Delta, because GC.com isn’t on the Delta shopping portal. You’ll have to figure out your own numbers on these deals, using your own liquidation costs and credit card rewards, to be sure that they work for you.
Good luck and happy shopping!
Will you be taking advantage of any of these holiday shopping portal offers? Will you use them for any profitable MS opportunities? And importantly, do you have any data points of bonuses being paid or not paid by UPromise on the purchase of gift cards? Please let us know in the Comments!
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