When I woke up this morning, it was -21 degrees Fahrenheit. My car won't start. My dog won't even go outside to pee. So let me tell you, this roundup of the cheapest flights we've found to the beach…is an extremely selfish exercise…
Lucky for us, in the past week, our team of Thrifty Traveler Premium flight deal analysts have sent six awesome flight deal alerts to some of the best beaches the world over for trips this winter.
Whether you want a first class flight to Hawaii, to use your Delta SkyMiles to fly to Mexico, or a cheap escape to the Caribbean under $400 roundtrip, we've got something for you to get through this frigid weekend.
It's not going to break the budget to fly you and your group chat or even the whole family to a locale with full of sun and sand in 2026. Take a look.
U.S. Virgin Islands Under $399 RT
The U.S. Virgin Islands have all the sunny, warm vibes you're looking for in the Caribbean, but you never have to pull out your passport or clear customs on your trip!
We rounded up all the fares we could find to St. Thomas (STT) – searching from more than 200 U.S. and Canadian airports (see if yours is one of them!) to dig up this impressive list of fares in the $200s and $300s, roundtrip down to STT this winter.
Feeling warmer, already, right?
First Class to Hawaii for 40k Points
A trip to Hawaii is the antidote to warm your soul, but there is a single best way to fly to Hawaii: Hawaiian Airlines First Class on the 787 Dreamliner.
(Disclaimer: I just booked this deal for later this winter, and the thought of it is the only thing that's keeping me warm today!)
Using your Hawaiian/Alaska Atmos Rewards points, you can book these seats on certain dates for just 40,000 points each way! That includes some short connections on Hawaiian Airlines to other islands, too. (I booked SEA-HNL-OGG for two passengers for 80,000 miles. Amazing!)
Seattle (SEA) is where the brand-new Dreamliner planes can be found, but you can fly lie-flat on the older A330 airplanes from several other West Coast airports, too.
Cabo San Lucas, Mexico from $297 RT
Mexico's West Coast – specifically the southern tip of the Baja Peninsula – is a massively popular warm weather destination…and for good reason. The pristine weather and beautiful coastline landscapes make it one of the more scenic Mexican locales.
The popularity of the destination means airlines often compete to be the ones to fly you there, which is why prices on these nonstop routes dropped into the $400s, $300s, and even $200s roundtrip this winter!
Puerto Vallarta from 8,000 SkyMiles RT
You've been stacking up those Delta SkyMiles for a reason, right? Well…this is that reason.
Puerto Vallarta (PVR) flights don't often get cheap, but we found a workaround using your SkyMiles this winter!
This isn't even the full list of fares – including several below 20,000 SkyMiles roundtrip! And if you fly from Los Angeles (LAX), it's an astoundingly cheap 10,000 miles!
San Juan, Puerto Rico under $399 RT
Puerto Rico flight deals are becoming more and more common. At this point, you should never settle for anything under $396 roundtrip, which is exactly what we found with this flight deal.
This impressive list of fares from all over the United States down to San Juan (SJU) can fuel your travels this winter.
Spend some time in Old San Juan, hit up El Yunque National Forest, and enjoy the sunshine and beaches!
Fort Myers, Florida from $127 RT
A cheap flight to the Florida Gulf Coast is the easy button of beach flights. No passport required and a quick flight from most airports, a trip to or through the Gulf Coast can and should start in Fort Myers (RSW)!
This low fare from New York (JFK) is a great example, but you can find low fares from cities big and small down to RSW, too.
Bottom Line
Book a flight to the beach in 2026 – because you deserve it!
As we hit the coldest days of the year, we rounded up six options for you to book your beach escape. Fly to Mexico, the Caribbean, Florida, or Hawaii using cash or your points and miles this year.
