How to Optimize Chase Freedom, Discover it for Q1 2019

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If you don’t drive much and rarely succumb to the siren song of the drugstore candy aisle, the new 5% cash-back bonus categories for the Chase Freedom® might not exactly make your heart sing. For the first quarter of 2019, the bonus categories are:
Gas stations.
Drugstores.
Tolls for bridges, highways and roads.
You can earn 5% cash back on up to $1,500 in combined spending in these categories, after activation, through March 31, 2019. (All other spending on the card earns 1% back.)
How can you best maximize this bonus, even if gas, tolls and medicine don’t make up much of your budget? It’s all about planning ahead for future expenses — essentially setting money aside now for purchases you would make eventually anyway. (If you happen to have the Discover it® Cash Back credit card or another eligible rotating-bonus-category Discover card, your strategy is a lot simpler this quarter. Read on for more.)
Pay tolls in advance
You’ll earn 5% cash back not only if you swipe your Chase Freedom® at a tollbooth, but also if you use it to top off your balance on an electronic toll device like the E-Z Pass. Even if you don’t take toll roads often, this allows you to push your savings well into the next few months.
Why bother prepaying when you can just pay as you go? Because not every state allows you to use a credit card at toll booths. (Toll booths in New York, Maryland and on Florida's Turnpike, for example, accept only cash or an electronic toll device.) Prepaying will save you time while driving, help you avoid the inconvenience of not having enough cash on hand and, of course, get you 5% cash back.
Prep for flu season
The dark, cold post-holiday months are when illness rates spike. Load up on essentials like over-the-counter medications, hand sanitizer and tissues at drugstores this quarter. (Don’t forget the magazines — when else but a sick day can you properly catch up on celebrity gossip?)
If you normally fill prescriptions at a supermarket pharmacy, switch to a drugstore so your out-of-pocket costs earn you the bonus. While you’re waiting for the pharmacist, stock up on personal care items you can use for the next few months, too.
Another tip: If your local Walgreens or CVS sells gift cards to other retailers, those purchases can count toward the bonus, as well.
Speaking of gift-card strategies, you can also employ a similar one this quarter if you have an eligible Discover card, such as the Discover it® Cash Back. That card, too, earns 5% back in rotating quarterly categories on up to $1,500 in purchases each quarter after activation (1% on all other purchases).
For the first quarter of 2019, the Discover it® Cash Back card's bonus category is grocery stores. So use the card there, obviously, for household necessities and for any Valentine's Day or St. Patrick's Day gifts and decorations — but also keep in mind that most grocery stores also have gift card aisles, and the same strategy applies there. Stock up on gift cards to other merchants while also earning your bonus.
Save at the pump
Even if you don't drive much, you can still stack rewards by linking your Chase Freedom® to a program like Shell’s Fuel Rewards. You can save a few cents per gallon, plus get 5% cash back from Chase on the rest.
It may not add up to much, depending on how often you need to fill your tank. But it's still nice to be able to save some money without having to put in much effort.
You can also front-load your spending for the year by buying gift cards for any other retailers that might be sold inside the gas station store.
Don’t forget
With the Chase Freedom®, you must activate the bonus categories by March 14, 2019, to be eligible to receive the extra cash back. (You can receive rewards retroactively with the Chase Freedom®, but not with the Discover it® Cash Back or other eligible Discover cards.)
If you’re getting a Chase Freedom® card for the first time, it offers a sign-up bonus: Earn a $200 Bonus after you spend $500 on purchases in your first 3 months from account opening. The card also offers 0% intro APR for 15 months on purchases, and then the ongoing APR of 14.99%-23.74% Variable.
If you're new to the Discover it® Cash Back, you'll be eligible for a unique bonus that the issuer phrases this way: "INTRO OFFER: Unlimited Cashback Match – only from Discover. Discover will automatically match all the cash back you’ve earned at the end of your first year! There’s no minimum spending or maximum rewards. You could turn $150 cash back into $300." The card offers an intro 0% intro APR for 15 months on purchases and balance transfers, and then the ongoing APR of 17.24%-28.24% Variable APR.
on Chase's website
1.5%-5%
CashbackUnlimited Matched Cash Back
on Chase's website
1x-5x
Points60,000
Pointson Chase's website
1%-5%
Cashback$200
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