How to let your Holiday Spending Fly you for Free

The holidays don't need to break the bank


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There’s no getting around it. The holidays are expensive.

Whether you’re flying cross-country for an awkward post-election family meal or buying presents for each of your steadily multiplying nieces and nephews, things can get pricey damn fast. Other than just, well, not doing those things, I can’t offer a solution. 

But I can help you get at least some of that value back in the form of free travel. At the very least, I can show you how to save on the big travel necessities and avoid blowing your points on a bad value redemption.

Read on for my best points-based holiday tips.

Tip #1: Hit a new card’s bonus with your spending

One of the best ways to maximize your points and miles throughout the year is to consolidate your big expenses on a new card. By doing this, you’re able to hit the introductory offer quickly without adapting any of your other spending.

This logic applies to the holiday period, too.

While you might not have a singular big purchase (like a fridge or a laptop at other times), you’ll probably have a ton of small to medium expenses. If you’re flying home for Thanksgiving and Christmas, buying presents, cooking a huge dinner, or even going out for dinner more while friends are in town, there’s a good chance your monthly spending will be way up.

Opting to put those expenses on a card like the Capital One Venture Rewards Credit Card is an excellent idea. By hitting $4,000 within three months, you’ll earn 75,000 miles. Those are worth at least $750 but can stretch to over $1,500 if you transfer to a high-value travel partner. On top of that, you’ll be earning a bonus of 2x miles per dollar on everything you spend.

It’s also a good chance to open a card you might not typically hit the spending goal for. The Platinum Card from American Express, for example, might be a little out of reach for some. But with the added expenses on top of daily outgoings, a big points haul could be in sight,

Capital One Venture Rewards Credit Card

75,000 Bonus Miles

Offer Details:

75,000 bonus miles after you spend $4,000 on purchases in your first 3 months of account opening.

Why we like it

The Capital One Venture is an excellent go-to card for any traveler, thanks to its easy to navigate 2 miles per dollar on every purchase. With no bonus categories to consider, a reasonable $95 annual fee, and a strong intro offer worth at least $1,000 in travel rewards, Alec Baldwin might be onto something. 

  • 5 Miles per dollar on hotels, vacation rentals, and rental cars booked through Capital One Travel

  • 2 Miles per dollar on every purchase, every day

Pros

  • The Capital One Venture’s current intro bonus is worth $1,000 when spent on Capital One’s (recently revamped) travel portal or you can use your miles to cover your recent purchases.

  • A steady 2 miles per dollar on all purchases makes earning simple and lucrative. You’ll also grab 5 miles per dollar when booking through Capital One’s travel portal.

  • Its $95 annual fee is almost negligible, especially if the intro bonus is achieved.

  • Flexible miles allow for a wide array of redemption options.

  • You can enjoy two free visits to a Capital One Lounge each year.

Cons

  • Capital One lacks US-based airline and hotel transfer partners.

  • Not many major perks beyond its miles value.

Tip #2: Be opportunistic

The holidays are no time for cowardly points and miles tactics. Be bold. With so many group events, like work parties, Friendsgiving, family dinners, nights out, and family flights, you have the chance to capitalize.

If you’re out for dinner with friends, take the check yourself and earn a ton more points with a card like the Gold Card from American Express or the Chase Sapphire Preferred. If you’re comfortable chasing everyone down for the money, a big bill could fly you somewhere amazing.

Here’s a hypothetical. If you paid for a $1,200 dinner tab with the Gold, you’d have 4,800 Amex points. With another $300 in groceries on the same card, you’d have 6,000 points—enough to fly from New York to London with Virgin Atlantic.

Chase Sapphire Preferred® Card

60,000 Bonus Points

Offer Details:

60,000 Bonus points after you spend $4,000 on purchases in the first 3 months from account opening.

Why we like it

The Chase Sapphire Preferred Card is the ultimate all-around travel credit card—it fits perfectly into almost any points-earner’s wallet. Points novices can enjoy a significant intro bonus and easy to grasp spending categories with an approachable annual fee. The more experienced can utilize its high value earning potential as a secondary card and also gain access to Chase’s strong travel booking portal.

  • 5x  on travel purchased through Chase Travel℠.

  • 3x on dining, select streaming services and online groceries.

  • 2x on all other travel purchases.

  • 1x on all other purchases.

  PROS

  • Get 25% more value when you redeem for airfare, hotels, car rentals, and cruises through Chase Travel℠. 

  • The $50 dollar hotel credit for stays purchased on the Chase Travel Portal already cuts the already approachable $95 annual fee significantly.

  • A 10% annual points bonus is tacked on every year, adding a little more value.

  • A free year-long Doordash DashPass membership is also thrown in, which gives you free delivery and some extra discounts. It’s a solid perk if you order food delivery at least semi-frequently (Activate by 12/31/2027).

  • Along with all of the above, cardholders also have access to a string of travel protections like rental coverage, cancellation insurance, and purchase protection.

  CONS

  • Maximizing the value of Chase points can still be complicated for complete novices.

    Competing cards like the Capital One Venture have a better earning rate for non-bonused spend.

    It’s subject to Chase’s 5/24 rule. So, if you’ve opened five cards in the last two years, you’re most likely not going to be accepted.

Tip #3: Leave no stone unturned

Most credit card issuers have shopping portals of some description. At any time of the year, you’ll find hundreds of points-earning deals there. While it’s a good habit to check in on these regularly, I get that it can be a bit tiresome. But the holidays are the best time to push through the mundanity.

You could even be strategic and only buy gifts from stores with deals. For example, if Lululemon has a 6x points per dollar deal, guess what your sporty niece is getting? If Dicks has a 10x points per dollar deal, your little cousin better enjoy his new Nikes.

This is a simple way to maximize things. Remember, if you’ve opened a card, too, you’ll be earning the introductory offer and these bonus points.

Tip #4: Add an authorized user

If you have multiple people spending in your household, be it a partner or a responsible kid, adding an authorized user to your card can be a great move. Even if your partner has rewards cards of their own, they might not have the same ones, leaving a hole in their spending. Grabbing an extra card means they can use the same tactics mentioned above and double down on the points. Just be careful not to accidentally pay for each other’s gifts with the card. Christmas ruined.

Tip 5: Don’t blow your points on flights

Christmas and Thanksgiving are some of the busiest times of the year for travel. And that chaos means ticket prices will soar. This can be a frustrating moment for points and miles enthusiasts because, as more airlines switch to dynamic systems, the points rates can also soar.

When faced with paying an annoyingly high cash price or an equally high points rate, many will cave and go for the money-saving option. Generally, I’d advise against this, as those points could go a lot further in the future. If money isn’t an issue for you, it’s often worth just coughing up the cash. Award chart systems can work but with availability low, you may need to be way ahead of the game.

One way to combat this is to have a store of points with an airline that doesn’t work in this way, like Southwest. Southwest does operate a dynamic system, but instead of fluctuating on its own scale, the rates remain tied to the cash price. In other words, if the cash price goes up, the points go up in direct correlation. 

While this won’t get you outweighed value, it is hard to get bad value. I always recommend opening one of Southwest’s co-branded cards. This saves you from transferring general points which could go further elsewhere. Open the card, hit the bonus, and keep the points ready for a situation like this.

Southwest® Rapid Rewards® Premier Business Credit Card​

60,000 Bonus Points

Offer Details:

60,000 Bonus points after you spend $3,000 on purchases in the first 3 months from account opening.

Why we like it

The Southwest® Rapid Rewards® Premier Business Credit Card is the airline’s middle-tier business card and offers perks for flying Southwest, plus benefits like travel protections and no foreign transaction fees. It’s easy to maximize for those who fly Southwest just once a year, as benefits like the 6,000 anniversary points and two EarlyBird Check-In® per year more than cover the annual fee.

  • 3X pts on Southwest® purchases.

  • 2X pts on Rapid Rewards® hotel and car rental partners.

  • 2X pts on local transit and commuting, including rideshare.

  • 1X pts on all other purchases.

Pros

  • Earn 60,000 bonus points after you spend $3,000 on purchases in the first 3 months from account opening

  • Earn 3X pts on Southwest® purchases, 2X pts on Rapid Rewards® hotel and car rental partners, 2X pts on local transit and commuting, including rideshare, and 1X pts on all other purchases.

  • 2 EarlyBird Check-In® per year—Get automatic check-in to enjoy a better boarding position and earlier access to overhead bins.

  • You’ll get 6,000 points every year after your first cardmember anniversary. Those points are worth about $80 towards Southwest flights.

  • Lost luggage and trip protection benefits.

  • No foreign transaction fees.

Cons

  • Southwest points cannot be transferred or used with any airline partners.

  • No statement credits

Quick fixes

All of the suggestions above are applicable if you’re in good financial standing and are comfortable spending money. But not everyone is so secure. If you’re strapped for cash, points, miles, and credit cards can represent an extra lifeline.

If you have points available, you can redeem them for gift cards or online purchases. While neither of these options will get you the best value for your points, they are direct savings for you.

The point

The holidays are an expensive time for everyone. Using one or more of these strategies can help you recoup some of that spending and even save money over Thanksgiving and Christmas. Just make sure not to spend more than you can afford.

Editorial Disclaimer: Opinions expressed here are the author’s alone. This post contains references to products from one or more of our partners and we may receive compensation when you click on links to those products.

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