The Cheapest Spots to Fly to in the Caribbean this Winter

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The Cheapest Spots to Fly to in the Caribbean this Winter

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Firing up the furnace for the first time is a drag. But you can take warm, sunny, tropical solace in the fact that cheap flights to the Caribbean aren’t hard to find.

For months, my fellow Thrifty Traveler Premium flight deal experts and I have been scouring the globe for cheap flights. And we keep finding low fares to destinations around the Caribbean for the winter.

How cheap – and where? We’re talking roundtrip flights to places like the U.S. Virgin Islands for $200 or less. Getting to Turks and Caicos for less than the price of your annual Netflix subscription. Or heading to Jamaica in January for the cost of what you usually pay to fly to Florida.

We continue to find roundtrip flights to places like Turks and Caicos, Jamaica, and the U.S. Virgin Islands for the same price as your annual Netflix subscription. Here are all the destinations in the Caribbean that stand out for cheap flights this winter.


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U.S. Virgin Islands

With no passport required and no COVID-19 test required to fly back to the mainland, there are plenty of reasons the U.S. Virgin Islands are a great spot for a trip this winter. And that’s before you consider the stunning and secluded beaches of St. Croix, St. Thomas, and St. John.

In the past, flights to St. Thomas (STT) or St. Croix (STX) would regularly top $400 or more. But in the past year, we keep finding fares to the U.S. Virgin Islands under $200 – from all across the country!

We found this shockingly low fare to St. Thomas (STT) this week and sent it straight to Thrifty Traveler Premium subscribers inboxes. Go figure these fares didn’t last long at this price, but you can still nab a deal for next summer.

msp to st thomas fare 

We’ve also found St. Croix (STX) deals over the last few months that would tickle any traveler’s fancy.

Cheap flights to the Caribbean 



If Jamaica floats your boat, take a look at this deal sent to Premium subscribers last month – for deeply discounted tickets all the way through spring 2022!

Cheap flights to the Caribbean 

It’s not just major airports getting the deals, either. We love deals that get smaller airports involved: We find flight deals from 175-plus U.S. airports – and Canada too. Fortunately, Birmingham (BHM), Chattanooga (CHA), Roanoke (ROA), and Scranton-Wilkes Barre (AVP) all got in on the action with this deal connecting travelers with one of our favorite Caribbean islands.

Why stop the savings with flights? One great part of visiting Montego Bay (MBJ) are Hyatt’s all-inclusive resorts: The Ziva and Zilara Rose Hall. It’s a great option whether you want an adults-only retreat or a vacation with the whole family. Best of all, they’re easily bookable for just 25,000 points per night to make most of your vacation free.


The Bahamas

The Bahamas are an attractive destination because they’re so close to the United States, but they feel a world away. And fares to get there this winter have been tumbling, too.

Cheap flights to the Caribbean 

Lately, we’ve seen flights starting at just $198 roundtrip from the U.S. to enjoy all of these spotless skies and clear blue waters.

Cheap flights to the Caribbean 

Have a Chase credit card like the Chase Sapphire Preferred® Card? Through the Chase Travel Portal, this deal was bookable for just 15,000 Chase Ultimate Rewards points (or less!) Can you think of a better use of those points? I’ll wait.


Turks and Caicos

A flight to Turks and Caicos is typically quite expensive, but these flight deals have changed that.

Paying $700 or more to get down to Providenciales (PLS)? Forget that. How about $225 roundtrip instead? 

Cheap flights to the Caribbean 

This deal we sent to Thrifty Traveler Premium members last week is gone now, but it included a bunch of nonstop routes from New York City-area airports (JFK, EWR), Miami airports (MIA, FLL), Atlanta (ATL) and Boston (BOS). Or you could make a quick connection from far-flung cities like Destin (VPS), Hartford (BDL), Gulfport (GPT), and Mobile (MOB).

Grace Bay in Turks and Caicos is home to one of the most pristine beaches on the planet. I haven’t been yet, but at these prices, my excuses are dwindling.

Cheap flights to the Caribbean


The Dominican Republic

The Dominican Republic has as much to offer as any Caribbean destination. It’s an island rich with culture and also features the beaches and weather any traveler would love during the winter months.

Check out this deal, featuring 11 months of low, low fares to Punta Cana (PUJ), including tons of nonstops, including Minneapolis-St. Paul (MSP).

Cheap flights to the Caribbean 

Hoping to head there this winter? Take in a Dominican Winter League baseball game. If you think American football fans or foreign soccer fans are nuts, you’ll be blown away by the atmosphere at Dominican Republic baseball games – they make baseball games in the states look sleepy.


Bottom Line

I’m losing my sympathy for anyone who complains about winter. With fares to the Caribbean this low, you can change your own fortunes and book an escape to paradise. Leave the hat and mittens at home.

From The Bahamas to the Dominican Republic, keep your eyes on your inboxes Thrifty Traveler Premium subscribers, because the next cheap flight to the Caribbean is right around the corner.

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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