When to Book and Fly for Cheaper Holiday Trips in 2025

Learn the optimal days to fly, when to book, and how to stretch your points for cheaper holiday travel. When is the prime time to book Thanksgiving and Christmas flights this year? How can you stretch points to cover pricey holiday trips? Hosts Sally French and Meghan Coyle discuss holiday booking windows and money-saving strategies to help you land lower fares and avoid headaches. But first, they break down the latest travel headlines, including Bilt Rewards adding Etihad Guest as a transfer partner, bigger welcome offers now available on select premium cards, and Hilton’s new Outset Collection of boutique, design-forward hotels, with bookings opening in November. Then, Meghan and Sally discuss holiday travel tactics, with tips and tricks on the cheapest days to fly, new “sweet spot” booking windows, and when to use points — especially for last-minute fares. They also discuss smart layovers vs. flying nonstop during peak season, backup plans and alternate airports, and which airlines were most on-time this year. They review when travel insurance is worth it, AI tools people say they’re using for trip planning, and utilizing the post-Thanksgiving/pre-Christmas “sandwich season” for quieter, cheaper travel. They also answer a listener's question about using points to book American Airlines flights and explain how you can get more value out of your miles this season. Card benefits, terms and fees can change. For the most up-to-date information about cards mentioned in this episode, read our reviews: Citi Strata Elite Review: Premium Perks Can Offset Its Premium Fee https://www.nerdwallet.com/reviews/credit-cards/citi-strata-elite  Chase Sapphire Reserve Review: A High-End, High-Maintenance Card https://www.nerdwallet.com/reviews/credit-cards/chase-sapphire-reserve  Citi Strata Premier: Big Rewards Across Top Spending Categories https://www.nerdwallet.com/reviews/credit-cards/citi-strata-premier  Resources discussed in this episode: Bilt Adds Etihad Guest as Latest Transfer Partner https://www.nerdwallet.com/article/travel/bilt-etihad-guest  The Best Travel Credit Card Welcome Bonus Offers Right Now https://www.nerdwallet.com/article/travel/top-rewards-credit-card-offers  The Busiest Travel Days Around Thanksgiving In 2025 https://www.nerdwallet.com/article/travel/busiest-travel-days-thanksgiving  The Best Days to Travel Around Christmas In 2025 https://www.nerdwallet.com/article/travel/flying-for-christmas-best-days  Airline Miles vs. Cash Calculator https://www.nerdwallet.com/article/travel/calculator-should-you-book-a-flight-with-cash-or-miles   Want even more tips and tricks to get the most out of your travel dollars? Subscribe to TravelNerd, our free newsletter designed to help you crack the code on spending less on your travel.   In this episode, the Nerds discuss: Bilt Rewards transfer partners, Etihad Guest miles, boosted credit card offers, premium travel cards, Citi ThankYou Points, American Airlines miles transfer, Citi transfer partners, Hilton Outset Collection hotels, boutique hotel brands, holiday airfare trends, Thanksgiving airfare prices, Christmas airfare prices, Black Friday flight deals, Christmas Eve flights, Thanksgiving Wednesday travel, flexible holiday travel dates, holiday layovers vs nonstop, alternate airports travel savings, Amtrak as flight backup, on-time airline rankings, Southwest on-time performance, Spirit Airlines on-time performance, Delta flight reliability, travel insurance for weather delays, cruise travel insurance, nonrefundable trip protection, AI travel planning tools, and sandwich season travel. Learn more about your ad choices. Visit megaphone.fm/adchoices