I have a friend named Blake who texts me every January (once he gets tired of the cold) asking for help finding cheap flights to the beach. You know who never, ever gets a good deal on his winter escape? Blake. Don't be like Blake.
The lesson: Don't wait for the snow to fly to start thinking about your winter escape, because the best flight prices you're going to get for a sunny getaway are right now. Too often, we hear from travelers who wait until winter has already set in to book a trip to their favorite island paradise. That demand is a recipe for high flight prices.
I'll say it once and for all right here: If you wait to book your winter getaway until it's already cold out, you're way more likely to get fleeced on price. The best prices for flights to Florida, Mexico, the Caribbean and more warm-weather destinations are going to be found in the next 2-3 weeks.
October and November are what we affectionately call Booking Season, offering the best airfare prices for travel in several important times of the year, but none more so than the dead of winter. I'm talking about Delta SkyMiles sales to Mexico under 9,000 miles roundtrip, nonstop flights to the Caribbean islands in the $200s and $300s roundtrip, and even flights to Hawaii under $399 (or in lie-flat First Class for just 40k miles each way!)
If you're reading this in January (Blake…) then it's probably, too late. But if you read it in October or November, you're in the sweet spot to book your trip to paradise.
Why You Should Book Now
Late fall and winter is the off-season for most airlines. Even the biggest airlines like American, Delta, and United make their bones during the peak summer travel season. So, in an effort to fill planes and make money during those softer, quieter winter months, the airlines offer nice discounts in advance.
Right now, while most travelers are distracted by back-to-school and the impending holidays, savvy travelers are looking at booking their winter trips. Every day that we get closer to the holidays, many of these fares to places like Hawaii, Turks & Caicos, Sint Maarten, Jamaica, and more are ticking up, and up, and up …
If you look today, you'll find that the seat maps on many of these flights are still rather empty – meaning fares are likely to be cheaper. One of the routes we've seen tons of great SkyMiles fares on, for instance, is this Seattle (SEA) to Puerto Vallarta (PVR) route. So I took a quick look at the seat map … and it all of a sudden became clear why they're selling these flights for as little as 4,000 SkyMiles each way …
Our Thrifty Traveler Premium flight deal team searches for fares to PVR and dozens of other tropical destinations multiple times a day, and we've seen the same trend play out year-after-year. We've been finding some of the best deals of the year in the past few weeks for winter travel. We can't stand the idea of you overpaying for your big trip this year.
We're seeing big dips in pricing to tons of destinations, but you need to move quickly. So where should you be looking if you want a cheap flight to the beach this year?
We're so glad you asked…
Hawaii under $399 RT (Or Lie-Flat for 40k Miles!)
Thrifty Traveler Premium subscribers don't need me to tell them that Hawaii flight deals have been hot lately.
There's no bad time of year to visit the Hawaiian Islands, but the winter months when it's cold on the mainland is about as good a time as any. And if you time it right by avoiding the holidays, flights to Hawaii can be astonishingly cheap.
Here's a perfect example: We noticed several roundtrip fares to Hawaii drop into the $200s and $300s roundtrip. So we went ahead and searched from more than 200 U.S. and Canadian cities and found that you could find similar fares from coast-to-coast!
All of these fares are during the dead of winter (January-March) when you'll likely need a splash of Hawaiian sunshine the most.
And if you prefer to use your points and miles, this deal flying United nonstop to the islands is a boon, too. When you book with United's partners, you can save big, too – especially when booking with Turkish Airlines, allowing you to book these routes for just 20,000 miles roundtrip!
Finally, if you're looking for something with a little more style, this Hawaiian First Class flight deal can put you in one of these swanky suites for just 40,000 points each way! And believe us … these seats are worth every point.
Mexico under 19k SkyMiles RT (or under $397 RT)
Nothing screams winter escape like a cheap flight to Mexico, and luckily, fares have been remarkably cheap down south. These fares to Tulum (TQO) were the perfect example.
More than two dozen U.S. cities could take advantage of fares flying the major airlines down to TQO this winter, but if you'd rather head a little further north to Cancún (CUN) and its famous resorts, you might want to flex your Delta SkyMiles instead.
Those fares flying Delta to paradise are some of the lowest we've ever seen. Here's a free tip: If Delta offers you flights to CUN for just 8,000 SkyMiles roundtrip, take it!
That's also true for travelers looking to head to the west coast of Mexico to cities like Puerto Vallarta (PVR) and Cabo (SJD).
Some of these cities like Eugene (EUG), Pasco (PSC), and Oakland (OAK) never seen rates like these. This was a deal to remember.
The Caribbean
The airlines tend to guard their nonstop flights to the Caribbean with higher prices. They know most travelers will pay a premium to skip the layover. But if you book ahead of time, you can often catch the airlines selling these seats at much more affordable rates, like this long list of fares we pulled together about a week ago.
Flying American, Delta, jetBlue, and United, these nonstop flights are some of the cheapest you'll ever find to exotic islands like St. Kitts, Aruba, St. Maarten and more.
One of the safer bets for a cheap flight to the Caribbean this winter is to San Juan, Puerto Rico (SJU). The airlines serve the U.S. territory with hundreds of flights a day – giving you a great chance at scoring a fare in the $200s roundtrip like in this deal we rounded up for our members.
Costa Rica & Guatemala
Everyone wants to get to the islands, but many fail to consider going to Central America, where the weather is incredible, costs are cheap, and you can get away for less than $300 no problem.
This flight deal to Guatemala (GUA) is a great example. Wouldn't a weekend on the banks of Lake Atitlan feel pretty good after braving the winter cold?
Costa Rica is a more well-known tourist destination – with travelers flocking to the rainforests and beaches of that beautiful, welcoming nation. And while many travelers eye up Liberia (LIR) due to its proximity to the west coast, flying to San Jose (SJO) also puts you right in the center of this beautiful country … and for much, much lower prices like these.
Stay Closer to Home: Florida & Arizona, Too!
You don't have to dust off the passport to escape the cold, either. Cheap flights to Florida and Arizona have been abundant this Booking Season, too. This roundup of flights to Orlando (MCO) is a great example.
If you want to entertain the whole family and come home with some mouse ears on, you'll do a lot worse than these flight prices. But Florida's a big state, and some travelers might hope for something a little beachier than Orlando's parks. Enter: Fort Myers (RSW).
These flights to RSW airport all fell under $195 roundtrip during the peak winter season, giving you the beach, golf, or poolside getaway you know you're going to want come the dregs of February.
Finally, for those who want a to visit the desert instead, there's Phoenix (PHX), a favorite of many U.S. travelers who need a visit to the Valley of the Sun … all for less than $198 roundtrip, of course!
Bottom Line
If you wait for the snow to fly before you book your winter trip, you're putting yourself behind the eight ball – and possibly costing yourself thousands extra on your warm weather getaway.
You can escape the cold weather for some unbelievably cheap rates this winter, but to get the best prices, the savviest travelers are already looking and booking their flights. Don't get caught waiting and having to skip your trip entirely. Start searching for your winter escape flights now!
