Cheap Flights to the Caribbean: Your Antidote for Winter Blues is Here

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cheap flights to the caribbean

Cheap Flights to the Caribbean: Your Antidote for Winter Blues is Here

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We're in the depths of winter. Some of us are about to be covered in snow. And that means it's the perfect time to scheme up an escape to the Caribbean.

I'll level with you: There's a ton of snow in the forecast and my snowblower won't start, so this roundup of the best cheap flights to the Caribbean is as much about my own sanity as it is about your next vacation. Nothing cures my winter blues like looking through the best flight deals to the Caribbean our Thrifty Traveler Premium team has found lately. And trust me: There's plenty to look at.

Whether you're looking for a passport and hassle-free trip to the U.S. Virgin Islands for $270 or less, an exotic escape to the beaches of Turks and Caicos or Curaçao for $277 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's this or trying to fix my snowblower.


Caribbean Classics

When it comes to the Caribbean, nothing's easier than the U.S. Virgin Islands. Why? Because you don't need a passport to visit either spot – getting there and back is as easy as traveling to Chicago.

And if you time it right, it can be as cheap as flying to Chicago, too.

Syracuse to St. Thomas fare 

This fare was from a flight deal we sent Thrifty Traveler Premium subscribers just a few days ago. It could get you to St. Thomas for less than $300 from more than a dozen U.S. cities, including some availability for a last-minute spring break trip. Just a few days earlier, we found a similar deal to neighboring St. Croix (STX) with availability this fall.

New Orleans St. Croix fare 

If you're willing to dust off the passport, there are some other Caribbean hot spots that are ripe for cheap flight deals. And in some cases, all you need to pay are the taxes and fees.

That's right: With just a few thousand Delta SkyMiles, you could book your dreamy beach getaway and save that cash thanks to one of our favorite Delta SkyMiles flash sales.

SkyMiles deals from NYC 

Only our Thrifty Traveler Premium+ members get these award alerts to use their points and miles!

Whether it's a quick jaunt to the Bahamas for 14,000 Delta SkyMiles roundtrip or a trip to Santiago or Santo Domingo in the Dominican Republic for under 18,000 SkyMiles roundtrip, there were some great nonstop SkyMiles options for New Yorkers in this one.

The Cayman Islands, another Caribbean favorite, is well within reach for most of us. Seven-Mile Beach on Grand Cayman is one of the most famous beaches in the Caribbean. And whether you live in Providence (PVD), Kansas City (MCI), or all the way on the west coast in San Diego (SAN), you could get there for as low as $297 roundtrip with one of our latest finds.

Cayman Islands flight deal 

And finally, we'll take it slow in Jamaica. Montego Bay (MBJ) is another great Caribbean destination for cheap flights year in and year out. Luckily, 2023 is no different.


Philadelphia to Jamaica deal 

With fares like this one from Philadelphia (PHL), you can see why Jamaica has made this list, too.


The Most Unique Caribbean Destinations

Let's get off the beaten path with some exotic destinations where cheap flights may not be the norm … but where we've found some awesome deals nonetheless.

We'll start with the island nation of Curaçao, a stunning island covered in beaches and coves. It's the kind of out-of-the-box adventure that can cost a small fortune … but with fares as low as $349 roundtrip, it doesn't have to.

Curacao flight deal 

You can file Trinidad and Tobago in the same category. I'll cop to not knowing how beautiful these islands were until we found this deal. Now it's rocketing up to the top of my bucket list.

Cheap flights to the Caribbean 

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

Then, there's the so-called “Spice Island of the Caribbean” in Grenada. This is one of the most far-flung Caribbean destinations and certainly one of the quietest if you're looking for a true escape. And American Airlines wants to take you there on the cheap!

Grenada flight deal 

I'll let this photo do the talking for our next destination: St. Lucia.

Cheap flights to the Caribbean 

Getting from the west coast to the Caribbean for cheap is notoriously hard, but this flight deal we sent to Thrifty Traveler Premium members to St. Lucia (UVF) included both Los Angeles (LAX) and Las Vegas (LAS) with sub-$385 fares. And St. Lucia isn't just a beach trip, either: As you can see, it's a mountainous country, with tons of incredible hiking in the Pitons. It's bucket list fodder of the highest order, and deserves a spot on your list.

I may have saved the best for last, but I'm biased because I booked this latest flight deal to Cuba myself.

Havana Cuba flight deal 

If you're thinking, “Wait, can I go to Cuba?” The answer is yes! Thrifty Traveler co-founder Nick took a fantastic trip down there a few years ago, and he has a full guide on why you can – and should – visit Cuba.

I might just see you there! The first mojito is on me.


Bottom Line

This isn't just a list of the cheapest destinations in the Caribbean for a trip in 2023, it's also an exercise in sanity to plan a sun-splashed beach getaway during the depths of winter in North America.

Whether it's an off-the-beaten-path getaway to Cuba, a quick escape to the Bahamas using points and miles, or an easy-peasy hop down to the Virgin Islands, there's a cheap Caribbean flight to be found for every traveler.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.

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