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Insider’s experts choose the best products and services to help make smart decisions with your money (here’s how). In some cases, we receive a commission from our our partners, however, our opinions are our own. Terms apply to offers listed on this page.
The holiday shopping season is one thing that’s sure to up your heart rate — whether you love to shop or you’re feeling anxiety from all the obligatory money you’re about to spend, it’s an adrenaline-inducing experience.
If you’ve got the right strategy, you can quite easily save 30% or more on just about anything you’re trying to buy. It takes a bit of patience (and the right rewards credit cards), but once you’ve done it a few times you’ll be a pro.
I’ll demonstrate the power of stacking deals by saving 40% on an office chair I’ve been wanting.
We’re focused here on the rewards and perks that come with each card. These cards won’t be worth it if you’re paying interest or late fees. When using a credit card, it’s important to pay your balance in full each month, make payments on time, and only spend what you can afford to pay.
Yes, I’m in the market for an office chair. Mine has become tattered from all the intense sitting I perform during a work week.
There are myriad strategies you can use to stack deals. You don’t have to follow the below steps in this particular order — it’s just the process that works best for me.
Several cards offer a form of targeted rebates when making purchases at select merchants. American Express cards publish Amex Offers**, Chase cards issue Chase Offers, Citi cards issue Citi Merchant Offers, etc. These offers reward you after you’ve made your purchase. They aren’t a discount, promo code, or anything of the sort. Once your qualifying transaction posts, you’ll receive a statement credit as a reward.
Some offers are extremely niche (earn 15% back at the Aroma Cafe in Equatorial Guinea!), so the key is to locate an offer with a store that sells all kinds of things. For this example, we’ll use Chase Offers. As you can see, my Chase Freedom Flex℠ currently offers a 10% rebate at Overstock.com, with a maximum of $45 in rebates. In other words, I can get 10% back on up to $450 in purchases.
If at all possible, you should begin every online shopping trip with a shopping portal. Shopping portals will give you bonus rewards simply for clicking through to a merchant’s website via their link. They will track your activity during a shopping trip, note how much you spent, and award you a specific percentage or bonus points back. The shopping experience is identical to navigating straight to the merchant’s site.
There are a few things to be aware of with shopping portals. For example, cash equivalents such as gift cards usually are excluded from earning rewards. Some portals also may not accrue rewards if you use certain promo codes at checkout. Read the terms and conditions of the shopping portal you’re eyeing before you use it.
MaxRebates is currently offering 10% back at Overstock.com. That’s a higher return than other portals at the moment, so we’ll shop through this portal.
Cashback Monitor is an excellent resource to find which shopping portals are offering the highest return for your specific purchase. Simply enter the store at which you’re shopping, and it’ll give you the earning rates of dozens of shopping portals — so you don’t have to waste hours visiting different sites for the best offer.
There are often loads of promo codes with websites like Overstock.com. Browser extensions such as Capital One shopping and Honey can auto-search these for you. Alternatively, you may receive a special coupon directly from the merchant.
I received a 15% coupon on my first order from Overstock.com — more generous than any other code I could find. I’ll stack that with my order at checkout.
The card I’m using to leverage my Overstock.com Chase offer is the Chase Freedom Flex℠. It comes with an excellent return rate, especially for a $0-annual-fee credit card:
The current 5% rotating bonus categories are Walmart and PayPal. These categories are exceptionally easy to maximize — particularly PayPal. That’s because PayPal is a very common payment method when online shopping — Overstock.com being a perfect example. As long as you can pay with PayPal, you’ll get 5% back with the Chase Freedom Flex℠ up to spending limits through December 31, 2022, once activated.
The office chair I want costs $605. That’s a lot of money — significantly more than I’m willing to pay.
The 15% off coupon I received for being a new Overstock.com customer brings the price down to $514.25. This is the price that the shopping portal, Chase Offer, and bonus points for spending will use to calculate my return.
You can see the PayPal option just below the “Check Out” button. I’ll click that so I can use my Chase Freedom Flex℠ 5% bonus category.
It’s worth noting that my Chase Offer stated the following stipulation to receive the 10% rebate (up to $45):
“Payment must be made directly with the merchant. Offer not valid on third-party services.”
Data points show that PayPal almost always passes along the merchant information to Chase when making a purchase. There should be no issue when paying through PayPal — but if I don’t receive it, Chase has an out.
I’m confident I’ll get the 10% Chase Offer, however, so I’ll click PayPal as my payment method and then confirm the Chase Freedom Flex℠ as my payment option.
Many stores have a loyalty program that rewards you for every purchase. Overstock.com will provide you with 5% in rewards for every purchase. If you shop at a store often, you may consider these credits as good as cash. This is another layer you can add to your deal stacking.
The best card to use for large purchases is always the one with which you’re trying to meet a minimum spending requirement to earn a welcome bonus. There are many credit cards that offer welcome bonuses of 100,000 points or more right now. Some of these can be worth $1,000 or more in cash.
The Chase Freedom Flex℠ offers $200 after spending $500 on purchases in the first three months from account opening. With my above office chair purchase, that’s just enough to earn this bonus from a single swipe.
If all things go the way they should, and all bonuses and statement credits post, you can save the following on the above office chair purchase:
That’s a grand total of $238.60 in savings, or about 40% off — making my $605 office chair a much more palatable $366.40 out-of-pocket (and that’s not counting earning a welcome bonus offer from the Chase Freedom Flex℠ if you’re a new cardholder). You probably won’t be able to earn credit card welcome bonuses and new-customer merchant coupons with every purchase — but the rest of these strategies are easily recyclable.
Editorial Note: Any opinions, analyses, reviews or recommendations expressed in this article are those of the author’s alone, and have not been reviewed, approved or otherwise endorsed by any card issuer. Read our editorial standards.
Please note: While the offers mentioned above are accurate at the time of publication, they’re subject to change at any time and may have changed, or may no longer be available.
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