It’s last call for finding cheap flights to the Caribbean for this winter…unless you’re cool paying $800 or more per ticket, that is.
In the past 10 days, we’ve seen some of the lowest airfare of the year for flights down to places like the Cayman Islands, Sint Maarten, Aruba, Puerto Rico, and more, but we’ve already seen the best fares start to dwindle, and these lowest prices (think under $400 roundtrip) might not last the week.
According to data from Google Flights, the best time to book Caribbean flights to get the best deal is between 26 and 68 days before travel, with that 44-days-out mark being the sweetest spot. Depending on exactly when you hope to travel, that puts us squarely into that window right now.
The reality is that window is probably a lot narrower and a lot further out than Google’s data suggests, because many of the lowest prices have been on coveted nonstop routes or to islands that only have once-a-week service in many cases. That’s not a lot of seats the airlines need to fill, and once they sell the cheap tickets, it’s on to the $800 ones…or worse.
Don’t give up on that Caribbean escape just yet, though. There’s good stuff out there if you know where to look. And we do!
Where You Can Still Fly For Cheap
Flight prices fluctuate based on how many tickets on each plane have been booked, how close-in to travel we are, and a million other little factors the airlines build in. That means not every one of the fares below may be exactly the same as they were when we sent these deals to our Thrifty Traveler Premium flight deal alert subscribers, but all of these deals were sent within the last 17 days, with most of them coming in the last week or so.
That means there’s ample opportunity to make one of these fares yours if you get moving.
Aruba from $282 RT
One Happy Island, Aruba’s appropriately simple and beautiful moniker, can’t wait to have you. One of the furthest away Caribbean islands is not a slam dunk for U.S. flyers, especially if you want to fly nonstop…usually.
This year is different! Look at that list of nonstop flights to Aruba (AUA) on sale for at least half off in all of these cases. Miami flights to the Caribbean are always cheap, but even from New York City (LGA), you could snag these for just $299 roundtrip! (Yes, the price of this flight actually dropped by a few bucks since we sent this Thrifty Traveler Premium flight deal alert.)
Sint Maarten or Turks & Caicos Under $395 RT
You can’t go wrong flying to the islands of Turks & Caicos or a place like Sint Maarten, either. The two dreamy destinations are favorites among U.S. travelers looking for some sun, so when flight prices to both of them plummeted, we rounded them up for our Premium members in a matter of minutes.
Like the Aruba deal, this flight deal to SXM and PLS was stunning because it was the sought-after nonstop routes that were on sale for the best prices. It’s unusual for these routes to be so cheap, but when the airlines slash prices, I’d recommend you just take the cheap flight and run!
Providenciales (PLS) is the main airport in Turks & Caicos, but this February, another airport will open on the islands: South Caicos (XSC).
This tiny island with just a few resorts is the escape of all escapes, and American Airline’s new service from Miami (MIA) to XSC is putting travelers from all of these places in paradise for cheap this winter and spring, too!
Cayman Islands from $294 RT
They’re as tried and true as a Caribbean destination as it gets, and that’s because the Cayman Islands always deliver sun-soaked vacations.
Plus, Grand Cayman (GCM) flight prices have been shockingly affordable lately.
Some nonstop flights were included on this flight deal, but cities with connecting itineraries could also save big on this one. Flying from places like Nashville (BNA), Syracuse (SYR), and even Westchester County, NY (HPN) is under $400 roundtrip if you book right away.
Boston and its JetBlue hub stole the show with this sub-$300 roundtrip fare, though!
Puerto Rico Under $199 RT
No passport? No problem. Puerto Rico flights are about as easy as it gets for the U.S. traveler. The Caribbean island is just a hop, skip, and a jump away this winter…and it’s often priced like a regular domestic flight, too!
If you want to go to the Caribbean this year, you’re not going to find anything cheaper than this!
Delta to the Caribbean from 16K Points RT
If you’ve been saving points and miles for a vacation, you can do a lot worse than using them on these roundtrip, nonstop Delta flights to the Caribbean.
The trick? You’re not going to book with Delta SkyMiles, you’re instead going to transfer your credit card points to Delta’s airline partners Virgin Atlantic or Air France/KLM Flying Blue to book these Delta flights for a fraction of the cost.
Read more: This is Now the Best Workaround to Book Delta Flights for Fewer Points
I’ll admit that, despite being a flight deal expert, I did not know all of these routes even existed! And to book them for this few points is a steal. If you look at the same flights using Delta SkyMiles, you might see totals closer to 100,000 roundtrip.
Instead, take your credit card points from banks like American Express, Bilt, Capital One, Chase, Citi, and Wells Fargo, transfer them to either Virgin Atlantic or Air France/KLM’s Flying Blue program, and book these flights for way, way less.
These are the instructions we sent to our Thrifty Traveler Premium members that allowed them to book these fares this winter. We’ve heard from several members that are taking dream trips to places like Punta Cana (PUJ), Barbados (BGI), or St. Kitts (SKB) this winter, too!
Bottom Line
Unless money is no object for you, the clock is ticking on getting a good deal on flights to the Caribbean this winter.
We recommend booking your winter Caribbean flights this week to take advantage of some of these unbelievable fares to some of the world’s best islands. The deals won’t get better than they are right now.
