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 they're cold to book a trip to their favorite island paradise. That demand is a recipe for high flight prices.
Instead, take advantage of the best flight prices of the year and get ahead of booking a winter trip this year. Right now is when you're going to find the some of the lowest fares of the year for winter trips, so consider this your official warning: If you try to book your warm-weather winter trip around the holidays or after, the likelihood that you're going to get fleeced for your fare is much, much higher.
You might be looking at closer to $800-$1,000 roundtrip on many of the routes you'll see below $399 roundtrip below. Here's why.
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 going to be cheaper, too. The airlines want your butt in that seat, and they'll give you a nice discount if you book it right now. But as the fall rolls on, that seat map will get more and more crowded until, thanks to demand, the suckers booking in January are paying $1,000 roundtrip for seat 35B.
Our Thrifty Traveler Premium flight deal team searches for fares to all of these 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 $296 RT
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.
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This is just the latest flight deal we found, flying travelers from all over the Midwest, the Great Plains, and the West Coast out to the Hawaiian Islands starting at just $200 roundtrip.
Seat maps on flights to Hawaii are still light, but they're filling up fast. Make sure you snag those seats before it's too late.
Passport-Free Spots: Puerto Rico and the Virgin Islands
I know the feeling: You want something sunny, warm, carefree, and most of all, easy for your winter getaway. What you don't want is the paperwork and hassle of customs and immigration. But you also don't want to settle for Florida again.
In the United States, we're beyond blessed to have the U.S. Virgin Islands and Puerto Rico just a quick flight away!
A few weeks ago, we rounded up all of these sweet fares to St. Croix (STX) in the Virgin Islands, with the best availability in January from most cities.
If you're a traveler in Allentown, Pennsylvania (ABE), Milwaukee (MKE), or Providence, Rhode Island (PVD), I think you'd trade a dark, wintry weekend at home for one of these cheap flights to paradise, instead, right?
While cheap flights to the Virgin Islands aren't always easy to come by, Puerto Rico flights have been more of a sure thing lately. Why? The airlines are honing in on the island – big time.
Airlines big and small have been adding flights to San Juan (SJU) like crazy. Two airlines in particular – Frontier and JetBlue – have even established crew bases there to help increase service. Ten U.S. airlines will fly to Puerto Rico this year, including all the major U.S. carriers. As a result, there was an almost 40% increase in flying to Puerto Rico compared to pre-pandemic.
Forty percent more flights means that many more seats, which the airlines have to sell to someone. Let's make that someone you.
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This latest San Juan (SJU) deal featured more than 100 U.S. and Canadian airports flying down to SJU this winter, making for an ideal winter escape.
JetBlue to the Caribbean (and Lie-Flat, Too!)
JetBlue is one of the airlines that has laser-focused on Puerto Rico flights as part of a strategy overhaul. Also part of that strategy overhaul? Flying nonstop from the East Coast to wintertime leisure destinations all over the Caribbean and Mexico.
This latest sale on nonstop flights to the Caribbean and Mexico featured only peak winter season flying from November to February. It was an unbelievable sale of flights under $400 roundtrip, made even more insane by the sub-$300 and sub-$200 fares on here, too!
But that's not all. JetBlue is also flying its famous lie-flat JetBlue Mint seats to a few destinations down south this year, too.
If you are trying to fly from New York (JFK) to Aruba (AUA) or San Juan (SJU) this winter, you'd be hard-pressed to find a better way than in a lie-flat seat for just 26,000 British Airways or Qatar points!
You can turn points from any of the major banks to British Airways Avios or Qatar Avios. Or if you've got JetBlue TrueBlue points (or Amex, Chase, or Citi points you can transfer to JetBlue), you can also snag these flights for between 28,000 and 35,000 points each way, too.
JetBlue wants to be the one to take you from the East Coast to the beach this winter. So let them.
Sint Maarten from $300 RT
The Dutch island famous for its airport-adjacent Maho Beach is known for many things, but cheap flights is not typically one of them. Sint Maarten (SXM) flight deals are rare…but not impossible.
Just last week, we dug up some nonstop flights to SXM for our subscribers in six different North American cities, all for less than $437 roundtrip. While there were some sub-$400 fares on this deal, too, the rarity and nonstop nature of these fares are impossible to ignore if you live in any of these departure cities.
Plus, if you could secure one of these flights on Delta, they were eligible for the Delta Companion Pass you get with credit cards like the *delta skymiles platinum card* and the *delta reserve card*. That means you can fly your companion down with you for just the taxes and fees. We heard from a Thrifty Traveler Premium subscriber who did just that to make their romantic winter escape a reality this February.
Cayes of Belize from $329 RT
Look, I'm taking a few liberties on this one…because Belize is not an island. But just outside of Belize City (BZE), where these cheap flights will take you, are the renowned Cayes of Belize. These tiny island paradises are as idyllic a winter escape as you'll find in this hemisphere.
Our Chief Flight Deal Analyst Jon booked this nonstop flight from Minneapolis (MSP) to BZE last winter and had a chill retreat to Ambergris Caye. (He even wrote a Thrifty Tip for our subscribers based on his time down there.)
While Jon had to turn to some points and miles to make this trip affordable last year, our Thrifty Traveler Premium subscribers this year were able to take advantage for cheap in 2024 and 2025.
Punta Cana, Dominican Republic from $272 RT
The Dominican Republic and its many, many all-inclusive resorts is another great option for winter weary travelers who just want to get away this winter.
With fares dropping into the $300s and $200s roundtrip, an all-inclusive pool and beach getaway is well within reach for almost any traveler in one of these cities below.
If you've been saving up Marriott, Hilton, or Hyatt points, an all-inclusive getaway like this might be your cheapest vacation in years!
Read Next: How to Book Hyatt's Incredible All-Inclusive Resorts with Points
Montego Bay, Jamaica from $295 RT
Practically synonymous with the warm weather getaway is the island of Jamaica. You can practically hear the steel drums and taste the daiquiris through this photo.
With flights under $396 roundtrip, those are not the only reasons Jamaica should be on your list this year.
A flight to Montego Bay (MBJ) puts you straight in the heart of beach-goer territory in Jamaica. A roundtrip flight to MBJ is possible for way less than you may think, too.
With so many airlines offering service to MBJ, there's no wonder these seat maps are still looking empty for your 2025 winter trip.
Or Use Your Delta SkyMiles Under 29K RT
The Delta SkyMiles in your account aren't getting more valuable – they're not collector's items or keepsakes. Watching your collection of SkyMiles tick up and up and up is a bad travel strategy in general, because your points will never be more valuable than right now.
If you want to fly to the Caribbean this winter, that's never been more true.
These fares are long gone – join Thrifty Traveler Premium to get the next Delta SkyMiles deal in your inbox!
These Delta SkyMiles rates down to Nassau, Bahamas (NAS) are some of the best we've ever seen. All of the airports below benefitted from fares below 19,000 SkyMiles roundtrip!
We thought it couldn't get better than that, but then Delta slashed SkyMiles rates to the ever-expensive Turks & Caicos (PLS), too!
Turks & Caicos flights are routinely $800 roundtrip (or much, much more from some of these smaller airports), so these SkyMiles fares are a steal. When Delta runs one of these SkyMiles Flash Sales, take full advantage by flying somewhere you otherwise couldn't afford.
Bottom Line
If you wait for the snow to book your winter trip, you're putting yourself behind the eight ball and possibly costing yourself thousands 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, and don't settle for Florida! Start searching for your winter escape flights now!
