How to Earn 5X Points on All Your Holiday Shopping (Plus a $50 Bonus)

If you’ve been reading Inside the Upgrade for a while, you know I’m obsessed with helping people maximize credit card points on everyday spending. I’ve been using points and miles to fund my luxury travels for years, and holiday shopping season is honestly one of the best opportunities to rack up points fast. 

If you’re going to be generous, might as well earn some points for it, right? 😏

This December, I’m using a simple strategy that earns me 5x points on practically every purchase, plus a $50 bonus and extra rewards through Rakuten. 

Here’s a step-by-step guide to how you can do the same!

Earning Extra Points on Holiday Shopping: A Video Breakdown

The Secret to 5X Points on Everything: Chase Freedom Flex® + PayPal

This December, the Chase Freedom Flex® is offering 5% cash back on all PayPal purchases through December 31st (learn more here) . This is huge because PayPal is accepted at millions of retailers, both online and in-store.

Here’s the basic gist of this super simple strategy:

1. You pay for your purchases with PayPal
2. On PayPal, select to pay with your Chase Freedom card and earn 5% cashback
3. You can transfer these points to the Chase Sapphire Preferred® Card or Chase Sapphire Reserve® for travel redemptions

And just like that you’re earning 5% on every purchase up to $1,500 (and more on the extra $50 Rakuten bonus below).

Not sure how to transfer points for travel redemptions? I have a guide to Chase here and Upgrade University on maximizing points and miles right here.

Step 1: Get the Chase Freedom Card

You need: Chase Freedom Flex. This is a super easy card to hold onto because it’s free 🙂

Here’s what it offers:

• $0 annual fee
• 5% cash back on rotating bonus categories (you activate these quarterly, this quarter they have a December promotion for PayPal)
• Up to $1,500 in purchases per quarter at the 5% rate
• 1% back on everything else

New to Chase? You can apply for the Freedom card here and even get a welcome bonus (usually $200 after spending $500 in the first 3 months).

Step 2: Activate Your 5% Category

This is critical and easy to forget:

1. Head to this site and activate your quarterly cash back
2. You’re done!

Important: If you don’t activate, you only earn 1% back. 

Step 3: Pay with PayPal at Checkout

It’s pretty easy now to use PayPal at checkout. 

For online shopping:

• At checkout, select PayPal as your payment method
• Log into PayPal
• Make sure your Chase Freedom is set as your default payment method in PayPal
• Complete your purchase

For in-store shopping:

• Download the PayPal app if you haven’t already
• Add your Chase Freedom card to your PayPal wallet
• At checkout, use PayPal’s QR code or tap-to-pay feature
• The cashier scans it like any other mobile payment

Step 4: Transfer Your Points To Travel Rewards Credit Cards

This is where this strategy gets really powerful. Those 5% cash back earnings aren’t just cash. They’re Ultimate Rewards points that you can transfer to premium Chase cards.

The reason you want to transfer the points is that points in the Chase Sapphire Preferred and Chase Sapphire Reserve cards can be transferred to airline and hotel partners. 

This is how I book business-class flights on repeat. I earn Chase points, transfer them to, for example, Air France, and book business-class flights directly on Air France.

I have a complete guide to Chase and their transfer partners here. 

Step 5: Stack with Rakuten for a $50 Bonus + Even More Points

You made it this far! And now you get $50 as a reward 😎

What is Rakuten? Rakuten is a cashback shopping portal that pays you for shopping at stores you already use. You can earn Rakuten rewards AND credit card points on the same purchase.

Sign Up and Get Your $50 Bonus

Here’s how to get started:

1. Sign up for Rakuten using this link for a $50 welcome bonus
   
   
2. Set your payment partner to Amex or Bilt (what I strongly recommend):
   • After signing up, go to your Rakuten account settings
   • Look for “Select a Payment Partner” or “How You’re Getting Paid”
   • Choose American Express Membership Rewards if you have any Amex card
   • Or choose Bilt Rewards if you have a Bilt Mastercard to earn points on rent
   • This converts your cashback to transferable points (1% cashback = 1 point)

Why choose Amex or Bilt instead of cash?

• Both Amex Membership Rewards and Bilt points are transferable to airlines and hotels. This is just way more valuable than cashback.
• You’re collecting points in multiple programs that you can combine for bigger redemptions
• Amex points transfer to partners like Delta, Virgin Atlantic, Hilton, and Marriott
• Bilt points transfer to Hyatt, United, American, and others

How to Shop Through Rakuten

Before any online purchase:

1. Go to Rakuten first:
   • Visit Rakuten.com or use their browser extension. Personally, I love the extension because it just pops up when I’m on a website, instead of me remembering to go through Rakuten.
   • Search for the store you want to shop at
   • Click through to the retailer’s website
2. Shop normally:
   • Browse and add items to your cart like usual
   • At checkout, select PayPal as your payment method
   • Make sure your Chase Freedom is linked to PayPal
3. Earn multiple rewards on one purchase:
   • Rakuten cashback (converted to Amex or Bilt points)
   • Chase Ultimate Rewards points (5% via PayPal)
   • Earn your $50 welcome bonus after your first qualifying purchase

Example stack: Let’s say you buy $200 worth of gifts at Macy’s:

• Macy’s offers 10% back through Rakuten (rates vary by store and season)
• You earn: 2,000 Amex Membership Rewards points (if you selected Amex as your payment partner)
• You also earn: 1,000 Chase Ultimate Rewards points (5% via PayPal on your Freedom)
• Total: 3,000 points across two transferable programs

This is the power of stacking rewards: You’re earning multiple rewards on the same purchase. Chase doesn’t know or care that you went through Rakuten first.

Which Stores Work with This Strategy?

Major retailers accepting PayPal online:

• Amazon (for most purchases)
• Target
• Walmart
• Best Buy
• Home Depot
• Lowe’s
• Macy’s
• Nordstrom
• eBay
• Etsy

Popular stores on Rakuten with high cashback rates:

• Macy’s: Often 10%+ during holidays
• Sephora: Usually 4-8%
• Nike: Typically 5-8%
• Target: Around 1-2% (but every bit helps)
• Best Buy: Usually 1-2%

Real-World Example: Holiday Shopping at Athleta

Here’s exactly how I’m using this strategy for one of my holiday purchases.

The plan: I’m spending $250 at Athleta for holiday gifts for my family and a little something for myself (hey man, self-love never hurt anyone). Since Athleta is currently at a 10% bonus on Rakuten, this is extra awesome.

The process:

1. Go to Athleta’s site and activate the Rakuten referral popup
2. Currently seeing a 10% cashback on Athleta
3. Shop for gifts and add my own picks to the cart
4. At checkout, select PayPal and make sure my Freedom card is linked
5. Complete the purchase

What I’ll earn on this $250 purchase:

• 1,250 Chase Ultimate Rewards points (5% via PayPal)
• 2,500 Bilt points (10% back through Rakuten)
• $50 Rakuten welcome bonus (since this is over $50)

Total haul: 3,750 points plus $50 cash from one shopping trip. If I have similar shopping trips throughout the season and max out my $1,500 quarterly limit, I’ll rack up serious points for my next trip.

FAQs On 5x Points on Holiday Shopping

Bottom Line: Holiday Shopping Can Fund Your Next Trip With Credit Card Points

This strategy isn’t complicated, but it does require a bit of intentionality. Instead of just swiping your regular credit card, you’re:

1. Using a no-fee card (Chase Freedom) that earns 5% back this quarter (don’t forget to activate!)
2. Paying with PayPal to unlock that 5% rate
3. Going through Rakuten first to stack additional points and get a $50 bonus
4. Transferring points to Chase Sapphire Preferred or Sapphire Reserve for better travel value

So you’re essentially getting paid in points to do your holiday shopping. Those points can cover flights, hotel stays, or upgrades on your next trip.

If you haven’t signed up for Rakuten yet, now’s the time. Between the $50 welcome bonus and the holiday shopping you’re already planning, you could easily rack up enough points for a free flight.

Cheers to your next adventure ✈️🎄