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When You’re Cold, It’s Too Late: Book Your Cheap Flights to the Caribbean Soon

Attention Thrifty Traveler Premium members:

Attention Thrifty Traveler Premium members:

You’ve likely already received these deals. If not, log into your Premium deals hub to see every recent alert we've sent.

By the time it's miserably cold out where you live, it's too late to book a winter escape on the cheap. Lucky for you, me, and everyone else who's dreading winter weather, getaways to some of our favorite destinations in the Caribbean are cheap right now.

This roundup of the best cheap flights to the Caribbean is about preserving our collective sanities. Nothing cures winter blues like having a tropical trip on your calendar. And our Thrifty Traveler Premium team has found plenty of options for you recently.

Why? Well, airlines have beefed up their Caribbean routes in a big, big way this year. That means there are thousands more seats flying to some of our favorite destinations, and those seats are being discounted as a result.

Whether you're looking for a passport and hassle-free trip to Puerto Rico from $151 roundtrip, an exotic escape to the beaches of Turks and Caicos on a brand new route from 20,000 points roundtrip, or a honeymoon-ish jaunt to an island you've never heard of for cheap, there's no shortage of great spots for a warm-weather escape that won't break the bank.

So let's look at some cheap flights to paradise! It beats raking leaves.


No Passport, No Problem

Besides being so close to home, one of the best parts of Caribbean travel is how easy it can be for U.S. travelers. And there are no two easier destinations than the U.S. Virgin Islands and Puerto Rico … because you don't need a U.S. passport to reach these U.S. territories.

So if you're one of the many Americans waiting for the government to return their passports to them amid long wait times, I've got an idea for you. All you need is $198 – or less.

Puerto Rico flight deal 

We sent this flight deal to Thrifty Traveler Premium subscribers just a few weeks ago for travel to Puerto Rico this winter, and the fares were dazzling! Just$151 would get you a roundtrip flight from New Orleans (MSY). Even the most expensive fare on the list was from Little Rock (LIT), which was still just $198 roundtrip.

The U.S. Virgin Islands are high on many travelers' lists, too. Lately, cheap flights to St. Croix (STX) have been easier to find than usual.

St. Croix flight deal 

The beauty of this deal was how many airports were featured on the list. Cities like Cedar Rapids, Iowa (CID), Charleston, West Virginia (CRW), and Gainesville, Florida (GNV) all got in on the action down to St. Croix this winter.

USVI flight deal info


Caribbean Classics

The classics are the classics for a reason. The beaches of the Bahamas, Jamaica, and the Dominican Republic have beckoned Americans for decades, and that hasn't changed in 2023.

Because people love those Caribbean hotspots so much, the airlines have made big adjustments in the number of seats they fly there every day during the peak winter season. The end result? More cheap fares.

Bahamas flight deal 

The Bahamas aren't going to give your wallet much of a break when you get there, but the journey down to Nassau (NAS) doesn't have to be expensive.

NYC to Bahamas fligth deal 

These fares are gone now – get the next deal in your inbox with Thrifty Traveler Premium!

The same goes for Jamaica's Montego Bay (MBJ), which has a big network of nonstop flights throughout the U.S. And we've seen those fares drop recently, too.

Montego Bay flight deal 

And finally, the Dominican Republic – particularly the beach haven of Punta Cana (PUJ) – can also be ripe for inexpensive winter fares. This winter could be no different if you book soon.

Dominican Republic flight deal 

The cheapest fares on this recent find for our Thrifty Traveler Premium subscribers started at $233 roundtrip. But as you can see, a number of other airports were available for a just a few bucks more.

PUJ flight deal


Use Points & Miles for a Caribbean Getaway

Cheap flights are great, but I'll do you one better: Flights where you only pay the taxes and fees.

Using your points and miles to get to the Caribbean is always a great idea and can get you some fantastic value, too.

For instance, this brand new nonstop flight from Minneapolis-St. Paul (MSP) to Turks and Caicos (PLS) debuted at about $700 roundtrip and about 50,000 Delta SkyMiles roundtrip. Ouch…

But if you used a crafty workaround and booked that nonstop Delta flight with Virgin Atlantic Flying Club miles instead, it would only cost you 25,000 points total – maybe even less! Those points are easy to earn: You can transfer points to Virgin from all the big banks like American Express, Chase, and Capital One, among others.

MSP to Turks and Caicos 

These 25,000-point award seats were available on a number of dates in January, February, and March of 2024. Thrifty Traveler Premium members who were on top of things when they received this email got a fantastic redemption on this new, nonstop route.

MSP to Turks and Caicos 

Delta isn't the only airline running robust networks down to the Caribbean this year, though. JetBlue would like a word…

JetBlue points deal to the Caribbean 

JetBlue ran a huge, 20% off sale on their flights booked with TrueBlue points. Here's the result:

JetBlue Caribbean info 

From Aruba (AUA) to Barbados (BGI) and even the likes of Guadeloupe (PTP), this JetBlue sale was your ticket for peak winter Caribbean travel if you had some points to throw around.

Lie-Flat Business Class to the Caribbean?!

Let's see if we can't make this Caribbean escape even more luxurious. Have you ever thought about a lie-flat seat to the Bahamas?

You have now.

JetBlue Mint to the Bahamas 

Earlier this month, we found JetBlue Mint Business Class seats from Los Angeles (LAX) to Nassau (NAS) on sale for just $963 roundtrip, making for a dreamy beginning to a perfect winter escape.


Bottom Line

In a few months, you'll be dreaming of a sun-splashed beach getaway during the depths of winter in North America. But by then, it's going to be too late to get a good flight deal. Get ahead of your winter blues and put something on the books while prices are cheap.

Whether it's a passport-free jaunt to the Virgin Islands or Puerto Rico, a business class trip to the Bahamas, or an easy-peasy hop down to Jamaica or the Dominican Republic, there's a cheap Caribbean flight to be found for every traveler.

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