Podcast Summary: Smart Travel – "When to Book and Fly for Cheaper Holiday Trips in 2025"
Hosts: Sally French & Megan Coyle (NerdWallet Travel)
Episode Date: October 15, 2025
Episode Overview
In this episode of Smart Travel, hosts Sally French and Megan Coyle dive into the art of booking affordable holiday travel for the 2025 season. With a mix of NerdWallet insights, personal anecdotes, and data-driven tips, they break down when and how to book, which travel tools and strategies really help, and offer practical, timely advice on maximizing both points and dollars during one of the most chaotic travel periods of the year.
Key Discussion Points & Insights
1. Holiday Travel Spending and Data [09:45]
- Americans will collectively spend approximately $311 billion on flights and hotels this holiday season, according to NerdWallet's annual study.
- 45% of Americans plan holiday travel, with average expected spend at $2,586 (up $200 from the previous year).
Quote:
"What is even $300 billion? I feel like that's not a real number." – Sally [09:56]
2. When to Book for Best Prices [10:54, 11:44]
- Christmas & New Year’s: Prices trend lowest about 51 days before departure. For Christmas, that's around November 4th this year.
- Thanksgiving: Lowest average prices at 35 days pre-departure. For 2025, this suggests booking by October 23rd for the best fares.
- Price drops for holidays are occurring later in the year (about a week later than last year for Christmas, 10 days later for Thanksgiving).
Quote:
"PSA, you're welcome for listening to Smart Travel. If you want to travel for Thanksgiving, book now." – Sally [11:55]
3. Date Flexibility: The Cheapest (and Nicest) Days to Fly [12:14]
- Actual holidays (e.g., Thanksgiving Day, Christmas Day) are consistently the cheapest and least crowded days to fly.
- Other good options: Christmas Eve, Black Friday, or as far from the holiday as you can manage (e.g., flying the Saturday before Thanksgiving for savings).
- Traveling on the holiday often means still arriving in time for dinner and encountering friendlier airport atmospheres.
Quotes:
"People at airports are nicer on the actual holiday." – Sally [12:52]
"There's some camaraderie going on with the holiday travelers." – Megan [12:55]
4. Strategic Use of Layovers [14:03]
- While layovers typically introduce risk (missed connections, delayed bags), they can significantly reduce costs for holiday travel.
- Choose layover cities strategically: Prefer those near your final destination (e.g., Philly for DC-bound travelers, to allow for an Amtrak backup).
- Opt for airports with frequent connecting flights in case of disruptions.
Quote:
"Layover at your own risk. But I do agree often layovers are so much cheaper. So this is like big time gamble energy." – Sally [14:22]
5. Airports & Routes Flexibility [15:38]
- Sometimes flying into or out of a slightly farther airport is substantially cheaper—keep your options open.
- During holidays, typical patterns of flight pricing and availability may shift, so frequent comparison is crucial.
6. Using Points, Miles, and NerdWallet Tools [15:56]
- Cash fares spike at the holidays, so check for mileage redemptions, which are sometimes especially competitive for last-minute bookings.
- NerdWallet offers calculators to determine the current value of points/miles for different airlines and hotels.
Quote:
"Don't overlook looking at points now if you're not sure what your points are worth…" – Sally [16:15]
7. Other Savvy Savings & Trends [16:59]
- Over a quarter of travelers plan to stay with loved ones rather than pay for accommodation.
- About 30% of holiday travelers will use AI tools to help plan trips—a growing trend even if the tools aren't always pricing-accurate.
Quote:
"I feel like I'm seeing so many trend pieces these days about, you know, this being the first AI Christmas…" – Sally [17:15]
8. Dealing with Delays and Cancellations [17:46]
- Have backup plans (alternative airports, trains, flexibility in plans).
- Arrive early at airports; being present can help you jump onto alternative flights in case of delays.
- Plan for chaos, as full planes mean bigger knock-on effects with any disruption.
9. Most Reliable Airlines for Holidays [18:51]
- 2025 On-Time Standouts:
- Southwest (best reliability, not counting Hawaiian)
- Spirit performed unexpectedly well, even surpassing Delta over the summer.
- Hawaiian Airlines is the most on-time, but benefits from good weather and a small sample size.
Quote:
"Spirit beat Delta. It's something. Oh, my God." – Sally [19:38]
10. Travel Insurance Tips [19:42]
- Highly recommended for complex trips (especially cruises or those with significant nonrefundable outlays).
- Double-check what your credit card already covers, and pay attention to policy details (e.g., how 'lost' baggage is defined).
11. International & Off-Peak Travel [21:43]
- The "sandwich season" (between Thanksgiving and Christmas) is a mini shoulder season—less crowded, cheaper, even for international travel.
- Trending festive-season international destinations: Rio de Janeiro, Saint Lucia, Marrakech, Curaçao, and always-popular Hawaii.
12. Listener Q&A: Best Ways to Book American Airlines Flights with Points [23:14]
- Via Citi: Citi ThankYou points now transfer 1:1 to American Airlines. Recommend the Citi Strata Elite or Premier cards for this avenue.
- Via Chase/Amex: Can book AA flights through their travel portals, but not as transfer partners.
Notable Quotes & Memorable Moments
- “Is this these people's first day on earth? Like, sorry. Then you add the outrageous cost of holiday travel. No way.” – Sally [09:22]
- “One of my best redemptions ever was actually a points deal during the holidays. It was 11,000 American miles...LA to Hawaii because I was going there for New Year's Eve and a wedding of course.” – Megan [16:29]
- “I love the chaos. And I also love a good airport lounge. So I'm like, yo, this is just an excuse to go to an extra lounge.” – Sally [18:08]
- “Let's coin that term. I have not heard sandwich season before.” – Sally [22:23]
- “If there is an American Airlines lounge at your home airport, Bob, maybe consider that [Citi Strata Elite Card].” – Sally [24:11]
Timestamps for Key Segments
- Holiday travel spending data: [09:45] – [10:14]
- Best time to book Christmas/Thanksgiving: [10:54] – [11:44]
- Cheapest days to fly & date strategies: [12:14] – [13:50]
- Layover debate: [14:03] – [15:38]
- Points, miles, and last-minute tricks: [15:56] – [16:40]
- AI and holiday travel planning trends: [16:59] – [17:38]
- Tips for delay/cancellation readiness: [17:46] – [19:41]
- Most reliable airlines: [18:51] – [19:41]
- Travel insurance nuances: [19:42] – [21:40]
- International/sandwich season travel: [21:43] – [22:44]
- Listener Q&A: AA flight booking with points: [23:14] – [24:22]
Conclusion
This episode is packed with practical, up-to-the-minute advice for booking smart—and sanely—during the 2025 holiday travel rush. From pinpointing the best booking windows, leveraging points, and navigating travel chaos, to new trends like AI trip planning and evolving transfer partners, Sally and Megan offer frank, data-backed, and personal guidance for travelers looking to make the most of their holiday journeys—budget and all.
Find more:
- Follow Sally (@SaveWithSally) and Megan (@MilesWithMeganCo) on social for travel hacks
- Relevant NerdWallet holiday travel articles and points calculators linked in the show notes
- Subscribe to Smart Travel for more Nerdy travel strategies