Why NOW is the Time to Book Your Winter Getaway

Why NOW is the Time to Book Your Winter Getaway

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For those of us who (for some reason) live somewhere with pretty brutal winter months, a warm winter getaway is vital. Even if it’s just a weekend or a short trip, an escape makes surviving those months easier.

Though we know it’s painful to think about winter now while the weather is still gorgeous, you must think ahead. In fact, the best time to book your winter vacation is … right now. Here’s why.


Why You Need to Book Soon

Why do you need to start looking now? Because even though winter feels far away right now, you can often save on flights – especially to warm-weather and international destinations – by booking 90-plus days in advance. We often find that booking flights three to six months in advance is the sweet spot for finding cheap flights.

Starting your search three to six months in advance for a cheap winter destination also gives you some buffer time to wait for the best deal. Once it’s already winter, finding a cheap flight deal gets much more challenging. To ensure your winter getaway doesn’t break the bank, be sure to start with a cheap flight deal and build your trip out from there.


Tips for Booking a Cheap Flight for Winter

Now, don’t panic: You’ve still got plenty of time to plan!

The first rule of booking a crazy cheap winter getaway – or any cheap flight – is to be flexible! Let the cheap flight guide your destination choice and trip dates.

Instead of deciding on a location first, keep your mind and options open to whatever flight deal comes your way. Weren’t thinking of a trip to Florida, but saw us post a flight deal to the Keys? That’s your cue!



Google Flights Explore is the perfect tool to search for a cheap flight if you’re open on where to go.

Similarly, if you have the flexibility, don’t commit to exact dates or start booking hotel reservations or tours before you have a flight. It’s the most common and costly planning mistake that travelers make, often costing hundreds of dollars on flights by locking into dates too early.

Instead, let the flight deals come to you, and see which destinations match with your winter availability. You’ll be able to save more this way rather than picking dates first and being stuck to those travel dates.


How to Get a Cheap Winter Flight Deal

If you’re in the mood for an easy domestic getaway to beat the winter blues, head south.

Some of our favorite domestic winter destinations are Phoenix, Santa Ana, San Diego, New Orleans, Miami, Orlando, and Austin. Love winter and the hobbies that come with it? Keep an eye out for deals to Denver, Salt Lake City, and other places that will let you hit the slopes

Thrifty Tip: Need some ideas of what to do in these destinations? Check out our guides to Phoenix, New Orleans, and Orlando.

To get the best domestic flight deal, keep an eye on the cheap flights we post to our website each day! You can see these deals by signing up for Thrifty Traveler to get our free daily newsletter. We include which dates are available on every deal: pick which ones work best for you, and book the rest of your travel after you’ve got a cheap flight secured.

If you need to travel to a specific destination or on specific dates, we just may find a deal that works great for you! However, it’s never a bad idea to also set up a Google Flights Price Alert. You can track the prices over a few months on that specific date and destination, and book when it’s cheapest.


price alerts
Google Flights price alerts can help you zero in on the best time to book a cheap flight


Looking for something a little more tropical outside the mainland U.S.? We can help. Our Thrifty Traveler Premium service finds the hottest international (and Hawaii, Alaska, Florida Keys, and Puerto Rico) flight deals and instantly notifies our subscribers of the deal. These deals are $250-$500 off average airfare costs.

Here are some recent deals we’ve found in the past few weeks that are available during winter months:

  • 35+ cities to Turks & Caicos from $224 (Was: $550)
  • 100+ cities to Key West, Florida from $117 (Was: $450)
  • 80+ cities to Mexico City, Mexico from $199 (Was: $625)
  • 17 cities to Lisbon, Portugal from $445 (including Thanksgiving – Was: $800)
  • 30 cities to Cabo San Lucas, Mexico from $232 (Was: $575)
  • 8 cities to Curaçao from $274 (Was: $650)
  • [BIZ CLASS] 50+ cities to Havana, Cuba from $406 (Was: $850)
  • 30+ cities to Bermuda from $271 (Was: $525)


This is a great example of why being flexible can save you a ton. Let the crazy cheap flight deal guide your winter getaway choice!


Bottom Line

Winter is coming.

And it’s not too early to start planning your warm-weather getaway. In fact, this is the perfect time to start looking. Follow us and keep your eye out for a destination that catches your eye. Then book that cheap flight when you find it.


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Editorial Note: Any opinions, analyses, reviews, or recommendations expressed in this article are those of the author’s alone, and have not been reviewed, approved, or otherwise endorsed by any card issuer.

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