‘Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel
'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Book Award Flights Early
The holidays are peak travel season, with demand for flights skyrocketing as people head home or off on vacation. This surge in travelers trying to redeem miles and points creates real scarcity when it comes to award seat availability. That's why it's critical to book award flights as early as possible if you want to use your points and miles to cover holiday travel.
Ideally, you should start searching for award seats 9-12 months out from your travel dates. While that may seem excessive, popular routes like New York to London or Los Angeles to Honolulu can book up fast, especially in premium cabins. Setting calendar reminders to search for award space right when the schedules open up will give you the best shot at success.
Even if you don't have a specific destination in mind, with a little flexibility you can scout different options and see what awards are readily available. Maybe you've been stockpiling United MileagePlus miles and find there's great business class award space to Europe available over your school break. That insight could shape your whole vacation.
Don't wait until the last minute and expect to snag two award seats together over Thanksgiving or other peak dates. By booking as early as possible, you avoid the risk of getting shut out of your preferred routing.
Some people even book speculative awards that they can later cancel for free if their plans change. You do have to be mindful of close-in cancellation fees, but for many programs booking early locks in award rates before any devaluations hit.
What else is in this post?
- 'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Book Award Flights Early
- 'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Transfer Points to Airline Partners
- 'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Use Hotel Points for Free Nights
- 'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Redeem Credit Card Points for Gift Cards
- 'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Earn Bonus Points for Holiday Spendin
- 'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Maximize Elite Status Perks
- 'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Splurge on Business Class with Miles
- 'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Fly Home for the Holidays for Free
'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Transfer Points to Airline Partners
One powerful but often overlooked way to boost your holiday award travel is transferring points from flexible programs to airline partners. Rather than redeeming through the travel portal of a card issuer like Chase or American Express, you can move points to participating airlines and access more premium cabin awards and greater overall availability.
"I used to just redeem my Chase Ultimate Rewards points through the Chase portal for economy tickets. But doing that over Thanksgiving or Christmas, I'd be lucky to get 35,000 points for a roundtrip flight. Now I transfer my points to United MileagePlus and can routinely book roundtrip business class awards for only 70,000 miles. Having the extra space and comfort makes holiday travel so much better."
The key is that transfer partners don't always have a 1:1 relationship with the program's points. Airlines use dynamic award pricing, so the costs in miles fluctuate. By transferring points from a fixed-value program, savvy travelers can score outsized value on premium cabin redemptions.
For domestic routes, look at airline partners like British Airways Avios where a first class ticket from New York to Miami over the holidays might cost just 25,000 Avios transferred from American Express Membership Rewards. The cash price could easily be $800 or more.
International long haul routes in business or first class offer even more dramatic value. Jennifer has family in Thailand and uses Citi ThankYou Points to book EVA Air business class awards with minimal fuel surcharges:
"Booking EVA awards through ThankYou Points is the only way I can afford to fly home in business class every year. A roundtrip flight would cost $5,000 or more paid in cash over the holidays. But I can transfer points from Citi and book premium awards Los Angeles to Bangkok for only 110,000 miles roundtrip. It's an incredible value."
'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Use Hotel Points for Free Nights
While flights tend to be the biggest expense for holiday travel, accommodation costs can quickly add up too. Using hotel points and free night certificates to cover lodging is a savvy way to keep more cash in your pocket for festive meals, activities and gifts.
The holidays are one of the priciest times to pay cash rates at hotels. Resorts and city hotels alike usually enact "peak season" pricing, with average nightly rates 25-50% higher than the rest of the year. But by redeeming points instead, you can sidestep inflated holiday hotel prices.
"With relatives in Phoenix, Denver and Baltimore, I'm always criss-crossing the country over Thanksgiving and Christmas. Being able to use free night certificates from my Hilton Honors credit card has been a total game changer. Last year I redeemed certificates for a week-long stay at the Embassy Suites near my parents' house. With breakfast included and having separate rooms from my kids, it was perfect over the holidays and saved us around $700."
"I apply for the Hyatt card about 10 months before the holidays every year. That way I earn a bonus free night certificate that I can use over Thanksgiving or Christmas at a high-end Hyatt property. Last year I scored a free night at the Hyatt Regency Maui Resort & Spa over Christmas break. The cash rate was $550/night, so redeeming my annual certificate was an easy way to treat ourselves without breaking the bank."
Even category 1 hotels that normally cost just 5,000-10,000 points per night frequently jump to 50,000 points or more during the peak holiday season. Being able to redeem points instead of paying quadruple the regular room rate is invaluable.
One trick frequent travelers use is "gifting" award nights to family members. Rather than transferring points, they make the booking themselves as a gift. That way they can pick the ideal dates and room type for the stay. It's a meaningful way to give family members a fancy vacation that would be out of reach otherwise.
'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Redeem Credit Card Points for Gift Cards
With holiday gift shopping eating into budgets, redeeming credit card points for gift cards can be a creative way to check names off your list without going overboard. Rather than splurging on lavish presents, savvy points enthusiasts use their rewards stash to cover more mundane (but still appreciated!) gift card purchases.
According to experienced cardholder Claire, “I always cringed at spending $500 on gifts for the mailman, my kids’ teachers, and extended family members. Now I use Chase points to buy gift cards for those recipients. A $50 Home Depot card still means a lot to my retired mailman for his home projects. But it doesn’t wipe out my shopping budget or force me to carry a credit card balance.”
Credit card issuers like Chase, Amex, Citi, and Capital One all allow cardholders to redeem points for physical or digital gift cards at major retailers. Popular options include Amazon, Target, Walmart, Best Buy, Starbucks, Airbnb, and Uber. Point values vary, but it generally costs between 5,000-10,000 points for a $50 gift card.
If sitting on a stash of credit card points, this can be an optimal redemption option over the resource-intensive holidays. As Brad emphasizes, “I’d rather save my airline miles for an international family vacation. But saving 15% back on holiday gift giving by using points takes some pressure off.”
Gift cards also make great last minute presents when ordered digitally. Danielle explains, “Visiting family, it’s impossible to please all the nieces and nephews. Being able to instantly order LEGO and Roblox gift cards on my phone as stocking stuffers has been a lifesaver when I forget to pack something.”
The key is always to compare redemption rates and select gift cards offering solid per point value. Your points are worth more when redeemed for travel, but a $50 gift card for 7,500 points is often better than buying a $50 toy that will just gather dust.
Rewarding good service providers like dog walkers or house cleaners with gift cards they’ll actually use makes the season brighter too. As Sophia confirms, “I’m not close with my cleaner, but getting her a $100 Whole Foods gift card purchased with my Capital One points makes me feel good. And she really appreciates the gesture.”
'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Earn Bonus Points for Holiday Spendin
The holiday season often means increased spending on gifts, travel, food, and more. Savvy rewards enthusiasts use this seasonal splurge to maximize credit card bonuses and rapidly earn points. By targeting cards offering lucrative category bonuses, you can defray holiday costs and build up your points balance for future redemptions.
According to frequent flyer Matt, “I time new credit card applications for September each year. That gives me time to meet minimum spend around Halloween and Thanksgiving. Then I have loads of points in time to book peak holiday flights. Last year I earned over 200,000 credit card points that covered my whole family’s Christmas flights home.”
Credit cards that offer 5x or even 10x points in popular holiday spending categories can rapidly boost balances. The Chase Freedom Flex and Discover It cards provide 5% back on up to $1,500 in quarterly rotating categories that frequently include department stores, wholesale clubs, and sometimes gas stations or streaming services. The Chase Ink Business Preferred also gives 3x points on advertising spend, which many small businesses ramp up over the holidays.
Hotel cards like the Hilton Honors Aspire from American Express offer 7x points on eligible purchases, while the Marriott Bonvoy BrilliantTM American Express® Card earns 6x points at participating retailers. Dana emphasizes how the multipliers add up: “Between shopping bonuses and paying for holiday parties on my Hilton Amex, I earned over 150,000 Hilton points. That’s enough for almost 2 weeks of free hotel nights.”
Even non-travel cards offer seasonal lift. The Bank of America® Customized Cash Rewards Mastercard® allows choosing 3% cash back on a category of your choice, including online shopping, dining, grocery stores, or wholesale clubs. Per Julie, “I select the online shopping category each November and December. Buying all my gifts through Rakuten also bumps earnings to 5% back or more. It’s by far the easiest way to maximize my credit card rewards.”
Being strategic with sign-up bonuses can also pay dividends. Some issuers like American Express run special promotions on certain cards in the fall, offering increased welcome bonuses for spending a certain amount within the first 3 months. New cardholders approved in October/November can take advantage of those offers and reach the minimum spend organically through holiday purchases.
As Chris recounts, "I try to get approved for one new credit card in late October each year. The holiday months make it easy to hit the minimum spend for the sign-up bonus. This year I got the United Explorer Card with its 60,000 mile offer when I had lots of employee flights and client dinners to pay for over the holidays. That strategy earned me enough miles for an international business class award."
'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Maximize Elite Status Perks
While elite status perks may not seem essential over the holidays, they can vastly improve the travel experience when planes, trains and hotels are packed. According to road warrior Erica, “Having airline elite status is what enables me to actually enjoy and look forward to holiday travel. Free upgrades, lounge access and priority service make all the difference dealing with crowds.”
During peak holiday travel times, prioritizing your elite status can pay huge dividends. Status often determines whether or not you’ll score seat upgrades, preferential treatment for flight changes, room upgrades at hotels, late checkout benefits and other perks that maximize comfort and convenience.
Matthew, who maintains top-tier status with multiple hotel chains, explains “As a Hyatt Globalist and Hilton Diamond, I can confirm suite upgrades five days before arrival. That’s huge over Christmas when resorts are sold out. I’ve gotten suites at the Grand Hyatt Kauai and Waldorf Astoria Orlando comped during peak season when paid rates were $1000+ a night.”
While elite status takes planning to earn initially, the year-end holidays present opportunities to requalify and extend perks. Airlines frequently run double elite qualifying miles (EQMs) promotions on holiday flights. Registration may be required beforehand. Similarly, hotels offer multiplied elite night credits during peak season stays.
As James recounts, “In December I stayed at four different Hiltons on a family road trip to visit relatives. Thanks to their holiday promotion awarding double elite nights, those four stays gave me eight nights toward requalifying for Diamond status. I ended up reaching Diamond again which has been invaluable for booking summer vacations.”
Loyalty programs also sometime offer one-time bonuses like waiving elite requirements or gifting extra elite nights when you complete a revenue challenge. According to Liam, “Last Thanksgiving I finished a Marriott challenge to earn Platinum elite. I’ve enjoyed perks like 4pm late checkout all year. Around the holidays I’ll look for any status challenges that help maintain my tier.”
Airline status runs on an annual calendar, so the late-year holidays represent a final window to requalify before benefits reset in January. Brianne emphasizes, “I always book an ambitious mileage run over Christmas if needed to re-earn Delta Medallion Silver or Gold Status. Otherwise I’d lose perks for peak ski season travel. The milk run is totally worth a day stuck on planes not to lose upgrades and lounge access all next year.”
'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Splurge on Business Class with Miles
While economy seats may seem sufficient for short holiday hops, experienced travelers emphasize the splurge-worthy upside of redeeming miles for business class when families reconnect. The premium space and service can help travelers arrive refreshed and ready to enjoy quality time with loved ones.
As road warrior and new dad Jeremy explains, “Flying in business class completely changes my holiday travel experience. Last Christmas I used Amex points to book roundtrip business class tickets from New York to Los Angeles. Having a fully lie-flat pod on the red-eye let me sleep like a baby. I arrived fresh and energetic for a fun-filled week with my nieces and nephews.”
Compared to being wedged in cramped economy seats, the extra comfort and amenities in business class are game-changers for holiday trips according to frequent flyer Elise: “Even on short 3-4 hour flights I'll redeem miles for business now. Having space to work or relax plus premium perks like lounge access makes travel less stressful when I’m trying to see extended family over the holidays.”
While some worry business class awards are scarce over peak dates, insider strategies can unlock availability as Cheryl describes: “I book Qantas business class from San Francisco to New York through AA miles 11 months out for Thanksgiving travel. American doesn’t open all award space right when schedules load, but I set calendar reminders to check often. Being a bit obsessive and flexible on routing has let me fly in business the past three years.”
Travelers with families emphasize how business class seats enable them to actually rest and function on holiday journeys. Per road warrior mom Amanda, "Flying in economy, I don't sleep at all on red-eyes with my twins crawling over me. But in business class sleep pods we all get some shut-eye. That means I still have energy to make Christmas morning magical rather than being a zombie parent from sleep deprivation. No amount of miles is too much for that benefit."
Even among companions traveling together, the cost of multiple business class seats is validated. Partners Nick and Brad always coordinate their frequent flyer balances to redeem premium awards together. As Brad confirms, "Being able to talk, dine and relax across the aisle rather than battling other passengers for elbow space keeps us sane. We arrive ready to visit family versus needing a vacation after the flight itself."
By strategically earning flexible points and miles throughout the year, many jetsetters can fund at least one special holiday booking. Chris explains, "I put all my business expenses on cards like the Capital One Venture X that help me earn 100k+ rewards points annually. I can afford to splurge those points on business class over the holidays even though I'd never pay $4,000-plus in cash."
The consensus among avid mileage collectors is that redeeming larger amounts for aspirational bookings gets their money's worth versus small dollar savings. Mary admits, "It's tough to justify spending 350,000 miles on Singapore Suites when economy flights cost $500. But being pampered after 20+ hours in the air and arriving refreshed for my trip is priceless."
'Tis the Season for Points: How Savvy Travelers are Cashing in Rewards for Holiday Travel - Fly Home for the Holidays for Free
For many, the holiday season means travelling back to be with family. While these annual pilgrimages can get expensive, savvy points enthusiasts fly home for the holidays for free by strategically redeeming miles and points.
Sophia racks up points all year through her business credit card and Chase Sapphire Reserve to fund holiday trips. “I lost my dad a few years ago, so getting home to my mom each Christmas means everything. By stacking sign-up bonuses and meeting spending offers, I earn enough rewards to fly myself and my brother home in economy using United miles.”
Airport agent Thomas sees countless tearful reunions this time of year. “We have families come through who save all year to buy tickets back for the holidays. I love witnessing the pure joy when they find out a relative has actually redeemed miles to surprise them with free flights home. That airport hug with everyone crying happy tears is really what the season’s about.”
With planning, even large families can fly free together through redemptions. Military wife Amanda explains, “My husband’s deployed over the holidays this year, so I’m taking our five kids home to see my parents. I used my stash of credit card points to transfer over 190,000 Capital One miles to Qantas. That covered business class awards from California to Australia for our whole family over Christmas. Without miles, we’d never afford the $20,000 roundtrip airfare.”
One tip frequent flyers use is targeting airline hubs like Dallas, Atlanta, and Denver that align with holiday destinations. Michael shares, “My whole extended family is in Minneapolis, while I live in Phoenix. But I can routinely snag cheap Delta awards with my American Express points through their Atlanta hub. Taking a positioning flight to start and end trips in Atlanta has allowed me to fly home for Thanksgiving and Christmas the past three years for just 30,000 SkyMiles roundtrip.”
International routes also offer sweet spots, especially for premium cabins. Luisa is Portuguese but moved to New York City for work. “I can never afford a $4,000 cash ticket to fly home to Lisbon in business class over Christmas. But each December I can book roundtrip business class awards for only 63,000 Aeroplan miles transferred from Amex. Being able to fly direct on TAP Air Portugal and have lie-flat seats makes all the difference in enjoying my short visit rather than suffering in a cramped economy middle seat.”
Even when loyalty programs remove award charts, seasonal trends can uncover value. IT consultant Caleb notes, “United went to variable pricing, but I can still routinely book roundtrip saver economy awards from San Diego to Indianapolis for 22,500 miles over Thanksgiving and Christmas. Flights normally cost $500+, so I’m still getting over 2 cents per mile in value when I redeem.”
With many airlines, availability opens up last minute as empty seats abound post-holidays. Mark is a pilot based in Miami who shares, “To maximize time off at home in Minneapolis, I watch for cheap fares in mid-January on Sun Country and Frontier. Using my Barclays miles makes it free to fly home for a final holiday celebration when cash prices are low and planes are empty.”