What Is Stacking, and Why Should You Be Doing It?

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When I’m talking about stacking, I’m not talking about stacking cups, although that is an impressive, yet useless skill.

I’m also not referring to the catchy Anna Kendrick song “Cups” from Pitch Perfect, where she never actually stacks anything.

Nope—when I talk about stacking, I mean the art of combining multiple deals to maximize your savings and points earnings. It’s one of those next-level travel hacking tricks that sounds complicated but often isn’t.

I consider myself more of a stacking hobbyist than a pro—someone who sometimes gets lucky when the right pieces fall into place. But you don’t need to be an expert to make this work. With a bit of awareness and timing, you can pull off some pretty sweet deals.

The specific offers and screenshots in this post are from a few years ago, but the strategy behind them still works today. Think of these examples as proof of concept. Whether you’re reading this in 2025 or beyond, the same tools—shopping portals, card-linked offers, limited-time promos—are still out there, waiting to be stacked.

Let me show you what I pulled off during one particularly successful week.

Amazon Prime Day & AMEX Membership Rewards: A Stacking Case Study

If you shop on Amazon, have a Prime membership, or simply exist on planet Earth, you probably know about Amazon Prime Day. This made-up shopping holiday launched in 2015, and it’s become one of the biggest online sales events of the year—especially for Prime subscribers.

While I initially scoffed at the idea (who needs another reason to spend money?), I’ve come around. Prime Day is actually a great time to knock out purchases you’ve been putting off—and if you know how to stack offers, the savings can really add up.

A few years ago, I caught wind of a special deal for American Express cardholders. By clicking a targeted link, eligible Amazon users could save 20% off their order just by using at least one Membership Rewards point at checkout. Yes, one point triggered the entire discount. Since paying with points on Amazon usually gives you terrible value, this was a rare exception worth jumping on.

And then came the stacking part.

Thanks to Frequent Miler’s tip, I realized I could apply the discount to a $500 order, including gift cards. So I bought $400 in Amazon gift cards and $100 in Outback Steakhouse gift cards—and paid just $400. Free steakhouse night? Yes, please.

But that wasn’t the end of it. On Prime Day, a set of Bose QuietComfort 25 noise-canceling headphones, normally priced at $249, dropped to $125. It was a good deal on its own—but because the AMEX 20% discount was calculated off the original $249 price, I got $50 off, making my out-of-pocket cost just $75.

Actually, scratch that. I used my previously purchased discounted Amazon gift cards to pay—so after all was said and done, I paid $73.69 for a $249+ pair of headphones. That’s the kind of stack you remember.

Most people probably flipped these headphones for a profit. Me? I kept them. In fact, I’m still using them to this day—years later. I replaced the foam ear cushions after they wore out, and I picked up an adapter to keep them compatible with my newer iPhone after Apple ditched the headphone jack.

AMEX Platinum, Saks Fifth Avenue & United MileagePlus Portal: Another Easy Stack

So, I lucked out on a deal. That won’t happen again, right?

Wrong.

It wasn’t luck—it was awareness. More accurately, it was paying attention to the offers already in my wallet and staying on top of the latest portal bonuses. Within a day of snagging the Amazon/AMEX deal, I spotted another opportunity I couldn’t pass up.

At the time, I had yet to use my AMEX Platinum card’s semi-annual $50 credit for purchases at Saks Fifth Avenue. Perfect timing because I also received an email promoting a portal bonus: 10 United miles per dollar when shopping at Saks through the United MileagePlus Shopping portal.

I’d just written about the value of using a shopping portal, and sure enough, Cashback Monitor had already flagged the flash bonus. Saks was one of their featured hot links—so I wasn’t the only one jumping on the offer.

I clicked through the United portal to Saks.com, picked out a few items I’d had my eye on (including a swimsuit), and built a cart for just over $50.

Final total: $54.42

• I earned 544 United miles (10x on the full purchase).
• I got $50 back from AMEX thanks to the Saks credit.
• My out-of-pocket cost? $4.42 for a swimsuit and some other “unmentionables.”

Final Thoughts: The Strategy Still Works

I’m not going to sit here and brag about how smart I am. What I will say is this: if you follow blogs like Frequent Miler and Doctor of Credit and keep an eye on your credit card offers and portal bonuses, you’ll start spotting these opportunities yourself.

These examples are a few years old, but the technique behind them is just as useful today. Whether it’s Prime Day or just a random Tuesday, you can still stack:

• Credit card offers (like AMEX or Chase Offers)
• Shopping portals (like United MileagePlus or Rakuten)
• Limited-time promos (bonus categories, gift card tricks, etc.)

Put those together, and you’re suddenly earning points, saving money, and maybe even getting a little thrill from pulling it all off.

So keep your eyes open, your portals bookmarked, and your credit card apps handy. With a little effort and good timing, you might find yourself paying $4.42 for a new swimsuit… or $73 for a pair of $299 headphones.

If you’ve stacked your way into a great deal recently, let us know in the comments—we’d love to hear what you pulled off!

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This post first appeared on Your Mileage May Vary