[Expired] Win 100,000 miles: enter by shopping or by mail

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Three major airline shopping portals are each offering the chance to win 100,000 miles and $2,500 ( that’s plenty of miles to fly first class to somewhere) for shopping between now and September 29, 2017 at 11:59pm ET — but you must first register / enter for all three. You can then gain entries by shopping through the portals or by mailing in index cards to Hello World. If that sounds familiar to you, you’ll understand why my wife rolled her eyes when I told her about it :-). If you missed out on IHG Priceless Surprises back in late 2015 / early 2016, it was a promotion where you could earn a bunch of IHG points for mailing in index cards. Read more about Greg’s experience here: IHG Priceless Surprises on track for more than 40K points despite hiccup. This time around, there is considerably less incentive to fill out so many postcards as there will be very few winners, but if you have time on your hands you can certainly get yourself in it to win it.

a woman serving a meal to another woman
100,000 miles is plenty to fly Cathay Pacific First Class….or go just about anywhere in economy class.

The Deal

  • Enter to win 100,000 miles and $2,500 (three “first prize” winners will receive 20,000 miles each) with American Airlines, United Airlines, or Alaska Airlines through their shopping portals
  • Click the image for each portal below and click “enter now”. Registering gets you 1 entry. Opting in for marketing emails gets you 100 additional entries.
  • Earn 20 entries each time you make $50 or more in purchases in a single day from a single merchant through the portal, up to 100 entries per day this way (alternatively, don’t buy anything and get your index cards and pens ready…read on below)


American Airlines
a screenshot of a giveaway

United Airllines

a blue and white rectangle with white text

Alaska Airlinesa screenshot of a video game

How to enter

Follow these steps:

Step 1

Click through to one of the shopping portals and click the “enter now” button as shown above. Then, you should receive confirmation that you are entered. If you are already opted in to receive email communications, you should automatically get 100 entries (as shown below). If you are not yet opted in to those, you’ll have the opportunity to do so.

a screenshot of a website

Step 2 Make purchases (or not)

You can gain further entries either by shopping. If you have purchases to make, you can earn 20 entires for purchases of $50 or more in a single day. This part is a little confusing, but as I read the terms, you will earn 20 entries for spending $50 or more with a single merchant in a single day, up to 100 total entries per day. To earn the full 100 entries, you would need to spend $50 or more with five different merchants. I’m basing that on this note:

NOTE: Multiple items purchased during one Day (“Day” is defined as 12:00 a.m. ET through 11:59 p.m. ET) with a single merchant, regardless of whether purchased in one or multiple transactions, are deemed a single Qualifying Purchase

In other words, if you make five purchases from a single merchant on the same day, they will count as a single purchase. You would have to spend $250 a day ($50 per merchant x 5 merchants) in order to maximize your 100 entries each day. The terms state the following about gift card purchases:

Gift cards may not count as a Qualifying Purchase; please read the terms of the merchant (from whom you are purchasing the gift card) to confirm if the purchase will count as a Qualifying Purchase.

I would expect that to mean that whether or not you get the entries on gift card purchases will probably come down to whether or not those purchases earn miles. You can check our Laboratory for results on buying gift cards through various portals.

However, you don’t actually have to make any purchases or opt in to marketing emails to enter 1,901 times with each shopping portal.

Entering by mail will cost you less money (but more time and hand cramps)

As was the case with IHG Priceless Surprises a while back, you can alternatively enter by mail without purchasing anything. The promotion terms state the following about entering by mail (bold type is mine, this example is from the American Airlines portal, but all three have a similar blurb):

Earn Additional Entries Without Purchase or Opting-in to Marketing Communications:

If you do not wish to opt-in to receive email marketing communications or make a purchase, hand print your name, address, day and evening phone numbers, email address, AAdvantage® account number, and date of birth on a 3″ x 5″ piece of paper and mail it in an envelope with proper postage to “AAdvantage eShopping℠ mall 2017 Getaway Giveaway Sweepstakes,” c/o HelloWorld, P.O. Box 5006, Department 831420, Kalamazoo, MI 49003-5006. You will receive one hundred (100) entries for each mail-in entry received; each mail-in entry must be sent in a separate envelope. You may mail-in up to nineteen (19) requests (each a separate envelope) during the Promotion Period to receive a total of nineteen hundred (1900) entries. All mail-in entries must be handwritten and must be postmarked by September 29, 2017 and received by October 6, 2017. All entries become the exclusive property of Sponsor and none will be acknowledged or returned. Proof of sending or submission will not be deemed to be proof of receipt by Sponsor. Sponsor is not responsible for lost, late, incomplete, invalid, unintelligible, illegible, misdirected or postage-due entries, which will be disqualified.

To recap, you need to send the following information on a 3×5″ card (each card in a separate envelope, up to 19 cards/envelopes):

  1. Name
  2. Address
  3. Day and evening phone numbers
  4. Email address
  5. Airline mileage account number
  6. Date of Birth

Mail your entries to the following addresses:

AAdvantage eShopping℠ mall 2017 Getaway Giveaway Sweepstakes
c/o HelloWorld
P.O. Box 5006
Department 831420
Kalamazoo, MI 49003-5006

MileagePlus® Shopping 2017 Bon Voyage Sweepstakes
c/o HelloWorld, Inc.
P.O. Box 5006
Department 831438
Kalamazoo, MI 49003-5006

Epic Escape 2017 Sweepstakes     (<–This is the address for Alaska Airlines)
c/o HelloWorld, Inc.
P.O. Box 5006
Department 831420
Kalamazoo, MI 49003-5006

No, that’s not a typo on both the Alaska and American entries going to the same department number….that’s what they each have listed online.

Is it worth it?

There’s no doubt that this effort will only really be worth it to the three people who win 100,000 miles and $2500. Maybe it would be worthwhile to some for the “first prize” of 20,000 miles. The last time Hello World handled one of these mail-in promos, some of our entries got lost / otherwise messed up, though we did get most of what we were due from that promotion. This time, it is a bit simpler since you won’t actually earn anything from each individual entry….though you also won’t know if the entries have been received and that also means it probably isn’t worth it to most people to fill out 57 index cards to enter.

Key notes

Three important things to note if you do this:

  1. The terms clearly state that you should hand write the entries. I don’t know if it will be enforced, but it’s not ambiguous. It says “hand print”.
  2. If you have opted in to marketing emails, you should only send 18 cards. The terms state that an attempt to enter more than the allowed number of times could void all of your entries, so this might be important. You get 100 entries from opting in to marketing emails, and I’d do that and save myself a little cramping and go with 18 cards. Maybe this doesn’t matter (I can’t imagine they would disqualify you because you made too many purchases), but I’d stay on the safe side with this.
  3. Be sure to postmark your entries by September 29th. I would suggest staggering your mailing — last time, I had more trouble with lost entries when I sent a ton on a single day. I’d separate this into at least 3 or 4 separate mail days if I were doing it.

Bottom line

Somebody is going to win 100,000 miles and $2500 from each of the three portals. A few more people will win 20,000 miles. I think the odds on this are too low to justify the time involved. However, the person who wins will vehemently disagree with me on that. I don’t know — maybe I’ll throw down with a few entries for the heck of it, but I doubt I’ll mail in the full 18 cards with each portal. But if you’ve got some free time over the weekend and a gambling spirit, you might toss some cards in the mail.

Are you planning to enter? Let us know if you win anything!

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Most pads of paper also come in 3×5 , no need to cut.
Also all need to be handwritten , even the envelopes.

Signed the sweeper. 🙂

I. Blair

As a stickler for rules I looked at each and the entry for the Epic Escape via Alaska air ends today 9-22 so entries must be postmarked by today.
In fact when going to their site it says this sweepstakes has ended.
The other 2 ends 9-29 postmark.

Also all require a 3×5 piece of paper NOT a card. Small detail that may disqualify the entry.


Very interesting observation on the piece of paper criteria…

[…] current drawings for 100,000 miles and $2500 at American, United, and Alaska shopping portals. See: Win 100,000 miles: enter by shopping or by mail for more […]


thanks a ton for the heads up!


Any idea if the envelopes need to be handwritten as well? I did this with the IHG promotion but I would love to be able to put labels on it this time…


How would you know if they lost your entries when their rules clearly state you won’t be notified of any received postcard mailings? To me, that means that you mail your postcards, then just wait.

What am I missing?