My family (25 of 32 people) just got back from a glorious Christmas trip to Costa Rica. We had a blast surfing, snorkeling, going on a catamaran, playing games together, and just enjoying each other’s company. My favorite part? Watching cousins hanging out together!

We gifted the Airbnb (expensive at Christmastime) to everyone, and almost everyone used points/miles to get there. We almost decided not to go during Christmas because the flights (just like the Airbnb) were about twice the cost. The families persevered and found flights they were willing to take. Did it mean they left super-early? Yes. Did they have to spend the night at a positioning location? Yes, again. Two families even had to come home a day earlier than everyone to get flights for better redemptions. It wasn’t as easy; it took work and sacrifice, but it worked out, and they all felt it was worth it.

Here are some examples of how using points for family holiday-season travel can help make a big trip happen, and what tricks can make a real difference.

 

Alex’s Example

When my mom first brought up the idea of a family trip to Costa Rica over Christmas, I was really excited. That is, until I saw the prices. Of course, traveling during the holidays means prices are super-inflated. We were looking at almost $12,000 for all six of us round-trip because it is such a busy time to travel. But thanks to points, we were able to make it work.

Because we have two Southwest® Companion Passes in our family, it made the most sense to fly Southwest Airlines®. I was not having much luck with our dates at first, but after talking to my sister, who had just booked her flights on Southwest, I decided to check flights for the day before our original departure.

Bingo. I found flights.

They were not cheap, but they were manageable. We paid 30.5K points per person for our flights there and around $500 per person for our flights home. To bring the price down even more, I used the 10% and 15% off coupons that come with select Southwest® credit cards each cardmember anniversary. These cannot be used on Basic fares, but they can be applied to points-and-cash bookings.

Unfortunately, our flight there included an overnight layover in Phoenix. I booked Home2 Suites by Hilton Phoenix Airport through the Chase Travel℠ portal and received $50 off by paying with my Chase Sapphire Preferred® Card, which comes with a $50 annual hotel credit. I also bought a bunch of snacks for my kids in the hotel lobby, and those were essentially free thanks to paying with my Hilton Honors American Express Surpass® Card, which includes a $50 quarterly Hilton credit.

On the way home, we ended up with another overnight layover in Denver due to a schedule change. I booked The Westin Denver International Airport, which is connected directly to the airport. This hotel is definitely not cheap, but since we were arriving after midnight, convenience was everything. Luckily, I found it in the Chase Travel℠ portal bookable with Points Boost, so I only paid 24,000 points.

On top of that, I contacted Southwest® to let them know how inconvenient the schedule change was. They ended up sending each of us a $50 Southwest® flight credit, totaling $300 to use toward future Southwest flights.

They were long travel days, but it was 100% worth spending a whole week in Costa Rica with almost all of my family. 

 

 

Kelly’s Example

We took our family of six to Costa Rica for Christmas. My husband and I both have the Southwest® Companion Pass and we were each able to bring a kid for free. Then I used points for another son and purchased one ticket for the 6th person. I also used a 20% off discount code for that ticket. In total, I spent:

• Points – 77k plus $84.98 in taxes, round-trip per ticket
• $752.01 for one ticket with 20% discount code

Total points and cash was $1,176.91 plus 231K points.

We had to leave at 6:05 am on Christmas Eve to get there and landed at home at 12:15 am on New Year’s Eve on the way back. We had layovers both ways at Hobby Airport in Houston. It was an early morning and a late night, but it was totally worth it, and we would do it again!

 

 

Using Points and Miles for Holiday Travel: What to Expect

Holiday travel can get expensive FAST! Flights sell out, hotels fill up, and prices climb. That is where points and miles can really shine if you know how to use them.

The biggest key is planning early. Airlines and hotels release a limited number of award seats and rooms for peak travel times. Once those are gone, the price of points usually jumps. Booking early gives you more options and better value.

 

Flights

Flexibility also matters more than ever during the holidays. Flying a day earlier or later, choosing a nearby airport, or even changing your departure time can unlock award space that wasn’t there before. A slight adjustment can save you a lot of points. I was talking to a nephew today, and he is planning a trip to Maui for his family during spring break. He was surprised at how much the price of flights was. I had to remind him that that is just like holiday travel, and he is pretty late to be planning for spring break, as it is already January. We looked at flights two days later, and there were a lot more options.

It is also normal to use more points for holiday travel than you would during slower travel seasons. Holiday demand is high, so award pricing often reflects that. The win is avoiding high cash prices, not chasing perfect redemptions. If a flight costs hundreds of dollars but a reasonable number of points, that is still a solid use.

 

Hotels

Hotel points are often a hidden advantage during holiday travel. Cash rates can skyrocket, while points pricing may stay more stable. Add in perks like free breakfast or late checkout, and hotel points can make busy travel days easier.

One more thing to expect is change. Weather delays, schedule shifts, and packed airports are common this time of year. Booking with points often gives you more flexibility to adjust plans, but it is still important to know your change and cancellation rules ahead of time.

Used the right way, points and miles can take much of the stress out of holiday travel. A little planning goes a long way, and your points can help you get where you need to go without overspending.

 

Points Talk Squad Holiday Travel Checklist

• Start planning early; award space disappears quickly

• Stay flexible with travel dates, times, and nearby airports

• Compare points prices to cash prices before booking

• Check airline partners for better award options

• Use hotel points on nights with the highest cash rates

• Review the change and cancellation policies before you book

• Keep some points available in case plans change

• Monitor your reservations for schedule updates

 

Bottom Line

It’s not impossible to travel with a family for the holidays and use points and miles. You do need to be more flexible, and that means being flexible with your expectations. Holiday travel is just more expensive.  

 

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