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by Rachel Cohen Rachel has turned points into long international vacations in business class for her family of six. She shares practical, approachable strategies for families who want to travel better for less.

Hi, Reader. One of my favorite ways to save on a purchase is to stack several different types of offers at the same time. Nothing gives a travel hacker a bigger dopamine hit than seeing four discounts land on a single purchase.

For any sizable purchase, I usually check five things:

• Card-linked offers, such as Amex Offers or Chase Offers
• ​Shopping portals, such as Rakuten or Capital One Shopping​
• Coupon codes
• Sales or rewards offered by the merchant itself
• Whether the purchase can help me hit a welcome bonus or other spending threshold

The annoying part is checking all of them. You might have hundreds of Amex Offers spread across several cards, a Rakuten rate that changes constantly, a coupon code floating around, and a spending threshold you are trying to hit.

This is where I've started using AI

First, I feed AI all of my card-linked offers so it has something useful to work with.

Amex doesn't have a simple button that exports your offers into a spreadsheet, but there is an easy workaround. I use CardPointers first to automatically add my Amex and Chase offers so I don't have to click through hundreds of them individually. Note that you need the paid tier to add multiple cards of the same type.

CardPointers has another particularly useful Amex feature: It can add the same Amex Offer across multiple eligible Amex cards before you manually add it to one card. Normally, once you add an offer to one Amex card, it can disappear from the others.

Once everything is added, go to the Amex website and open the Amex Offers & Benefits section. Click Added to Card, then View All.

Once the full list is displayed, press Ctrl+A, then Ctrl+C, and paste it directly into your AI of choice with Ctrl+V (use Cmd instead of Ctrl on a Mac). That gives the AI the full text of your activated Amex Offers in one shot.

If you have offers spread across several cards, repeat the process as needed and tell the AI which card each group of offers belongs to. Also mention if there's a card you want to prioritize for a welcome bonus or other incentive.

I use a prompt like this

Viator is a good example

Suppose you're booking $250 of tours and AI spots an Amex Offer for $40 back after spending $250.

That takes your effective cost to $210.

Then it checks Rakuten. Say Rakuten is offering 12% cash back at Viator, which would be another $30 on a $250 purchase.

Now the potential math is:

$250 purchase-$40 Amex Offer-$30 Rakuten cash back=$180 effective cost

That's already 28% back, at least on paper. This is where the last line of the prompt earns its keep: Rakuten's Viator terms currently exclude cash back when card-linked offers or discount codes are used, so a good answer should flag that $30 as at risk.

Then you can add another layer. Maybe there's a Viator coupon code. Or maybe you need another $1,000 of spending to earn a 100,000-point welcome bonus, in which case putting this purchase toward that requirement can make the transaction even more valuable.

Dell is where this can get particularly ridiculous

The Amex Business Platinum currently gives enrolled cardholders up to $150 in annual statement credits on qualifying U.S. Dell purchases, plus an additional $1,000 statement credit once you spend $5,000+ with Dell in a calendar year.

On top of that, I've sometimes had a separate Dell Amex Offer on the same card, and occasionally more than one Dell-related offer available across my Amex cards.

Then add Rakuten, which I've seen go as high as 20% back during promotions. Dell itself frequently has coupon codes and sales. And if you belong to Dell Rewards, eligible purchases can also earn Dell Rewards points that can later be redeemed as Dell Dollars.

A well-timed Dell purchase can therefore combine a sale price + coupon + Amex Business Platinum Dell credit + separate Amex Offer + Rakuten + Dell Rewards.

One caution: Shopping portals often say that outside coupon codes, card-linked offers, or other promotions can invalidate cash back. In my experience, purchases sometimes track and pay cash back anyway. I've also had good luck submitting missing-cash-back claims to Rakuten when purchases fail to track, and they often credit the cash back quickly. But if the published terms exclude part of a stack, I treat that piece as potential upside rather than guaranteed savings.

Checking for these stacks takes a few extra minutes, but on a larger purchase the savings can be substantial. And once AI is doing most of the searching and math, the process is much less tedious.