Extra Credit: How Back-to-School Shopping Can Pay for Your Next Vacation
Yes, buying crayons and lunchboxes could be your ticket to Cabo. Here’s how.
School supply lists are the real-life version of a teacher’s ransom note.
“Six glue sticks.”
“3 packs of pre-sharpened pencils.”
“A box of tissues the size of a carry-on.”
And while you’re swiping your card for all this stuff (plus the sneakers your kid swears make them “run faster”), you might as well get paid for it; in travel points. That way, your August spending spree funds your next beach trip, ski weekend, or “please, someone feed me wine” escape.
Let’s talk strategy.
Step 1: Pick the Right Card for Your Shopping Haul
Back-to-school shopping isn’t a quick errand — it’s a full-blown points-earning opportunity. The key is knowing which card to use depending on where you’re buying:
- Chase Sapphire Preferred® or Reserve® → Use through the Chase Ultimate Rewards® Shopping Portal for bonus points at places like Staples, Walmart, and Dell.
- Amex Gold Card → 4X points at many department stores and big-box retailers via gift cards or online orders.
- Chase Freedom® or Freedom Flex® → 5X on Instacart, as a rotating quarterly bonus category that includes school supply stores like Target, Office Depot, and Staples.
- Store cards? Nah. Unless they come with a monster signup bonus, your flexible travel points are way more valuable.
Step 2: Stack Those Shopping Portals
Before you click “add to cart,” check cash-back and points portals like:
- Rakuten (earn Amex Membership Rewards points instead of cash back)
- CashbackMonitor
- Airline Shopping Portals (AAdvantage eShopping, Alaska Shopping etc.)
Pro move: Click through the portal first, then pay with your travel rewards card. That’s double the earning — and you didn’t even have to do extra math.
Step 3: The Gift Card Hack
Some stores don’t code as bonus categories for your credit card. Sad trombone.
Solution: Buy store gift cards at a location that does give you bonus points — like an office supply store (5X on some cards) or a grocery store (4X on Amex Gold). Then use that gift card for your back-to-school haul.
Yes, it’s a little roundabout. But so is the school car line, and you survive that.
Step 4: Don’t Forget the “Non-School” School Stuff
This is where the real juice is. Back-to-school isn’t just pencils and glue — it’s:
- New backpacks (ie: personal item carry-on for your kid’s next trip)
- Laptops and tablets (hello, tech purchase bonus categories)
- Lunchboxes and reusable water bottles (also handy for Disney days)
- Clothes and shoes for fall (bought via a portal, of course)
All these purchases rack up points if you swipe strategically.
Step 5: Redeem Like a Pro
If you’ve earned enough from your August splurge, you might already have a free flight or hotel night by fall break.
A few quick-win redemptions:
- Southwest Wanna Get Away fares for a family trip.
- Hyatt Category 1–4 hotels for a weekend getaway.
- Transfer points to airlines for those sweet, sweet low-mileage award deals.
Final Bell
Back-to-school season doesn’t have to be a financial black hole. With a little stacking, portal-hopping, and smart card use, you can turn those school supplies into a boarding pass.
So while your kid is learning algebra, you’ll be learning how to sip a margarita at a resort you booked entirely on points — all thanks to glue sticks and binders.
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Jacqueline Gomez
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All information is accurate as of the date of publication but may change over time.
Always check for the latest details before making travel plans.
