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 around the holidays can get pricey very quickly.

Luckily, I can help you get some of what you spend back in the form of free travel (or cash back). At the very least, I can show you how to save on the big travel necessities and avoid blowing your points on a low-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 onto a new card and earn its welcome bonus, which can be worth thousands of dollars in travel. This way you can hit the minimum spending requirements quickly without having to change your spending habits.

This logic applies to the holidays, too.

While you might not have a singular big purchase (like a fridge or a laptop), you’ll probably have a ton of small to medium expenses. If you’re flying home for the holidays, buying presents, cooking a huge dinner, or even going out for a meal 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 new card, like the Capital One Venture Rewards Credit Card, for instance, is an excellent idea. By spending $4,000 within three months of opening the Venture card you’ll earn 75,000 miles. Those are worth at least $750 in travel, but can easily be worth over $1,500 if you transfer your miles to one of Capital One’s travel partners. On top of that, you’ll be earning 2x miles on every spending category, so your rewards will rack up quickly no matter what you’re buying.

It’s also a good opportunity to open a card that you might not typically be able to reach the spending requirements for. The Platinum Card® from American Express, for example, might normally be a little out of reach for some. But with the added expenses of the holidays on top of your normal day-to-day purchases, a big points haul could be in sight. You can earn 80,000 Membership Rewards® Points after you spend $8,000 on purchases in your first 6 months of card membership.

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 on all these events.

If you’re out for dinner with friends, pay the bill yourself and earn a ton more points with a card like the American Express® Gold Card or the Chase Sapphire Preferred® Card, both of which are some of the best cards for dining purchases. Have your friends Venmo or Zelle you for their portion of the bill, as a hefty check could actually result in you flying somewhere amazing.

Here’s a hypothetical. The Amex Gold card earns 4x points at restaurants worldwide (on up to $50K in purchases per year) and 4x points on groceries at U.S. supermarkets (on up to $25,000 in purchases per year). If you paid for a $1,200 dinner tab with the Amex Gold, you’d have 4,800 Amex points. With another $300 in groceries on the same card, you’d have 6,000 points total—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 and airlines have shopping portals of some description which allow you to earn bonus points or airline miles for purchases you were already going to make (and this is on top of your credit card points). 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 Nike has a 10x points per dollar deal, your little cousin better enjoy his new shoes.

This is a simple way to maximize things. Remember, if you’ve opened a new card, too, you’ll be earning the welcome bonus offer, the bonus points from the shopping portals and points from your regular credit card spend. That’s a great way to triple dip!

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 account can be a great move. Even if your partner has a rewards card of their own, they might not be using the best card, leaving a missed opportunity to maximize rewards. 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 award pricing, the points rates can also inflate.

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 award availability low, you may need to be way ahead of the game when booking travel.

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 pricing 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 amount of points needed goes up in direct correlation.

While this won’t get you outsized value, it’s hard to get bad value from your points. I always recommend opening one of Southwest’s co-branded cards. This saves you from transferring bank points (i.e. Amex, Chase or Citi points) which could go further elsewhere. Open the card, hit the spending requirement to earn the welcome 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 than points, miles, and credit cards can represent a lifeline.

If you have points available, you can redeem them for cash back, gift cards, or online purchases. While neither of these options will get you the best value for your points, they will provide you direct savings and spare you from opening your wallet.

The point

The holidays are an expensive time for everyone. Using one or more of these strategies can help you recoup some what you spent in the form of free travel or cash back. 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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