Summer's Over: It's Time to Book Your Cheap Flights to the Caribbean

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Summer’s Over: It’s Time to Book Your Cheap Flights to the Caribbean

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I'm just going to come right out and say it: Summer's over. You can either mope through your fall and winter, or find your own summer with a cheap flight to the Caribbean. Your choice.

For months, my fellow Thrifty Traveler Premium flight deal experts and I have been scouring the globe for cheap flights and low fares to the Caribbean keep popping up over and over again.

How cheap – and where? We're talking roundtrip flights to places like the U.S. Virgin Islands, Turks and Caicos, the Cayman Islands, and Cuba. Or heading to Jamaica for just the cost of the taxes and fees.

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, 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!

This month, we dug up these Virgin Islands fares and sent them straight to Thrifty Traveler Premium subscribers' inboxes.


Virgin Islands flight deal


We love St. Thomas flight deals, but we especially love getting St. Croix involved. It's one of Chief Flight Deal Analyst Jon Shallbetter's favorite spots, and he wrote you a handy guide to plan your trip if you can book this sweet deal.

One of the great parts of this deal is the inclusion of airports like Destin (VPS) and Syracuse (SYR). Travelers there won't get awesome Caribbean deals every day like people in New York and Miami are used to, but these fares from the smaller airports are fantastic.



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


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.

But there's an even better deal to Montego Bay (MBJ) that I want to show you.


Montego Bay SkyMiles


Yeah…that's right! Starting at just 11k Delta SkyMiles roundtrip, you can visit Jamaica for just the taxes and fees. It was a great find by our Premium team and led to some insane value for travelers.

Why stop the savings with flights? One great part of visiting Montego Bay (MBJ) is 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 the 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 $266 roundtrip from the U.S. to enjoy all of these spotless skies and clear blue waters.


Nassau Bahamas


Lots of American travelers got in on this fantastic deal, but look at all those Canadian cities, too! Thunder Bay (YQT), Toronto (YYZ), and Montréal (YUL) all were able to find fares for less than $400.

Have a Chase credit card like the Chase Sapphire Preferred® Card? Through the Chase Travel Portal, this deal was bookable for just a few Chase Ultimate Rewards points, too. 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 $280 roundtrip instead? 


Turks and Caicos fare


This fare was part of a deal we sent to Thrifty Traveler Premium members this month. It's gone now, but it included a bunch of nonstop routes from New York City-area airports (JFK, EWR) and Miami (MIA). Or you could make a quick connection from far-flung cities like Columbus (CMH), Gainesville (GNV), Providence (PVD), or San Jose (SJC).

If you're in need of a reason to get to Turks and Caicos, Grace Bay 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


Cayman Islands

Nothing screams island time like the Cayman Islands. The ultra-laid-back Caymans are known for beautiful beaches, accessible wildlife, kayaking, snorkeling, and so much more.

The Caymans haven't always had the reputation for the cheapest flights, but we've been poking holes in that idea for months now.


Cayman Islands flight deal


This Cayman Islands deal offered tons of sub-$400 roundtrip fares, including some mind-blowing deals from Allentown (ABE), Erie (ERI), Manchester (MHT), Rochester (ROC), and White Plains (HPN) among others.



This might surprise you, but you can visit Cuba. And you absolutely should.

If you follow our guide, it's really not hard to visit the stunning Caribbean island just a stone's throw from Miami. It feels a world away culturally, but it boasts those same beautiful beaches and perfect weather to which most travelers are accustomed to in the Caribbean.

And coming out of the pandemic, cheap flights to Cuba have been abundant, especially on American Airlines.


Cheap flights to Cuba


I booked this deal from Minneapolis (MSP) for next April and I couldn't be more excited. Hopefully, some of our subscribers in Cleveland (CLE), Chicago (ORD), Philadelphia (PHL), or Richmond (RIC) can join me down there!



Aruba is not a cheap place to fly. But what if I told you you could book a flight there for $90 roundtrip?


Aruba flight deal


This American Airlines AAdvantage miles deal to Aruba left our heads spinning. Just 20k miles roundtrip and $90 in taxes and fees could get you to the tropical paradise during peak winter and spring 2023.

Save your dollars for a fancy night out after a day of exploring the caves, beaches, and rock formations of Arikok National Park, which encompasses 18% of the country of Aruba.


Bottom Line

With fares to the Caribbean this low, you are running out of excuses on why you can't book your escape to paradise this year. Leave the hat and mittens at home and enjoy yourself instead of being bogged down by winter this year.

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


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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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