When You Should Book Your Holiday Flights to Get the Best Deals (Plus Insider Hacks, Secrets, and Tips)

Ah, the holidays — that magical time of year when everyone is either rushing to book flights or scrambling to figure out how they’re going to afford getting home for the festivities. Whether you’re traveling to spend time with loved ones, exploring a winter wonderland, or jetting off to escape the cold, booking holiday flights can be expensive and stressful if you don’t plan ahead.

But guess what? It doesn’t have to be. With a few insider hacks and travel secrets, you can save yourself a boatload of cash, time, and frustration. Here’s everything you need to know about when to book your holiday flights for the best deals, and how to take your travel game to the next level with some pro tips.

When to Book Holiday Flights: The Sweet Spot

Let’s start with the big question: When should you book your holiday flights?

In a perfect world, you’d book as soon as your travel dates are locked in. But life doesn’t always work like that, and there’s actually a science to finding the best time to snag a deal. Here’s what you need to know:

1. Thanksgiving Travel:
   For domestic U.S. flights, the sweet spot to book your Thanksgiving flights is about 3–5 weeks before the holiday. That means by the end of October, you should have those flights locked in. Booking too early or too late can lead to price spikes, so mid-October to early November is your golden window.
2. Christmas & New Year’s Travel:
   For the December holidays, you want to plan a bit further out. The best time to book Christmas or New Year’s flights is 5–6 weeks in advance. By early November, you should be looking for deals and aiming to finalize by mid-November. However, if you’re traveling internationally, aim for 6–8 weeks out for the best deals.
3. Last-Minute Flights:
   If you missed the early booking window, all hope is not lost. Airlines often release unsold seats at discounted prices closer to the departure date, but these are unpredictable. If you’re a risk-taker, you can monitor prices up until 1–2 weeks before your travel dates for a potential last-minute deal. Skyscanner is perfect for this — it tracks fare drops and alerts you when prices dip. Always start your search there to make sure you’re not overpaying.

Travel Hacks to Score the Best Holiday Flight Deals

Timing is key, but it’s not the only secret to saving money on holiday travel. Here are some lesser-known hacks to help you fly smarter, without the hefty price tag:

1. Use Skyscanner to Compare and Save
   If you’re serious about scoring the best holiday flight deals, Skyscanner is your best friend. This site searches across airlines and booking platforms to find the lowest fares, and it offers flexible search options so you can compare prices on different days. Not sure if flying out on December 23rd or 24th is cheaper? Skyscanner will show you. Looking for a flight with an easy layover? You got it.
2. Tip: Use the “Everywhere” option on Skyscanner if you’re open to exploring new destinations for the holidays. You might find a hidden gem at a price that beats all expectations.
3. Fly on the Holiday Itself
   This may sound a little crazy, but flying on the actual holiday (Thanksgiving Day, Christmas Day, or New Year’s Eve) is often much cheaper than traveling the day before or after. Airports are quieter, flights are less crowded, and prices drop significantly because fewer people want to travel on the holiday itself. Think about it: arrive just in time for Thanksgiving dinner or a Christmas morning celebration, and save a ton in the process.
4. Take Advantage of the Midweek Trick
   Typically, the busiest and most expensive travel days are the Wednesday before Thanksgiving and the days immediately before Christmas and New Year’s. However, if you can be flexible and fly on Monday, Tuesday, or Thursday, you’re more likely to find cheaper fares. Midweek flights are often the least expensive — and yes, you’ll still get to your destination on time for the holiday.
5. Maximize Points and Miles with the Right Cards
   Want to save even more on holiday flights? Use your points and miles! If you’re not already earning miles with a travel rewards card, start today. I always recommend the American Express Gold Card as the best starting point. You can earn a massive 90K points when you sign up with my link. These points add up fast and can be redeemed for flights through Amex’s travel portal or transferred to your favorite airline. And once you’ve used your Gold card to its fullest, grab the American Express Platinum Card, which offers 150K bonus points — perfect for upgrading your holiday travel experience.
6. Remember: Timing matters here, too. Make sure you apply for the Gold card first, then the Platinum, so you get the full bonus for both.
7. Use Flexible Airports
   When booking holiday flights, don’t just search for your nearest major airport. Consider nearby alternatives. For example, if you’re flying to the Bay Area, don’t forget about Oakland (OAK), which often has cheaper fares than San Francisco (SFO). If you’re using Skyscanner, it will allow you to search multiple airports at once, so you can find the most affordable options within your range.
8. In the New York area? Compare flights from JFK, LaGuardia (LGA), and Newark (EWR). Sometimes you’ll find significantly better prices just by flying out of a different hub.
9. Book Round-Trip Flights Separately
   This one’s a hidden gem of a travel hack. Instead of booking a traditional round-trip ticket, try booking each leg of your trip separately. Sometimes, you’ll find a cheaper fare on one airline for your outbound flight and a better return fare on another. Skyscanner makes it easy to do this, and you can mix and match airlines to create your perfect, budget-friendly itinerary.
10. Get Nomad Health Insurance by SafetyWing
    Holiday travel can be unpredictable, and the last thing you want is to get sick or injured while you’re away from home. I always recommend Nomad Health Insurance by SafetyWing for affordable and reliable travel insurance. It’s designed specifically for travelers, so whether you’re hopping across the country or heading abroad for the holidays, you’re covered. Don’t leave home without it.

Other Secrets for Stress-Free Holiday Travel

In addition to booking your flights at the right time and using travel hacks to save money, here are a few more tips to help you enjoy smooth, stress-free holiday travel:

1. Sign Up for Fare Alerts
   If you have a specific destination and date range in mind, but you’re not ready to book just yet, sign up for fare alerts on Skyscanner. You’ll get notified when prices drop, so you can swoop in and book at the lowest fare. This is especially useful if you’re waiting for a sale or still finalizing your travel plans.
2. Consider Flying One-Way
   Don’t be afraid to break up your holiday travel into one-way tickets. Sometimes, you’ll find cheaper flights when you book two separate one-way tickets rather than a round-trip flight. Again, Skyscanner is your go-to here, allowing you to explore all of your options without restrictions.
3. Use Skyscanner for Hotels, Too
   Booking flights isn’t the only part of holiday travel that can be expensive — finding a decent hotel can also be a challenge. Luckily, Skyscanner lets you search for hotels and rental cars along with flights, so you can bundle your travel plans and potentially save even more. Pair it with Agoda to unlock crazy deals, sometimes up to 50–70% off, on luxury hotels. You’ll be traveling in style without blowing your budget.
4. Check Out Viator for Holiday Tours
   If you’re heading somewhere special for the holidays, don’t forget to check out Viator for local tours and experiences. Whether it’s a Christmas market in Europe, a Thanksgiving Day parade in New York, or a holiday light tour, Viator offers curated, high-quality tours that can make your trip even more memorable.
5. Use My Ultimate Travel Guides
   If the thought of planning all the details of your holiday trip feels overwhelming, don’t worry — I’ve got you covered. My Ultimate Travel Guides and Cheat Sheets take the stress out of vacation planning. I’ll create a seamless itinerary for you, covering everything from flights and hotels to must-see attractions and local gems. The best part? You can sit back and enjoy your trip while I do all the heavy lifting.

Final Thoughts: Let’s Make This Holiday Season the Best One Yet!

Holiday travel doesn’t have to be stressful or expensive if you know the tricks of the trade. By booking at the right time, using the right tools (like Skyscanner for flights and hotels), and leveraging your points and miles with the American Express Gold Card, you can enjoy a luxurious travel experience without going over budget.

And don’t forget — you don’t have to do it all alone. Let me handle the planning with my Ultimate Travel Guides, so you can focus on what really matters: enjoying your time with family, friends, and loved ones this holiday season.

Until next time here’s to smooth skies, good company, a journey full of happy memories. I’m your Travel Hack Guide to affordable luxury tips. Catch you later. Peace

Travel Hack Guy

ZachusTravel.com & YouTube.com/zachustravel