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Baby it’s cold outside. In some places anyway. But not in the tropics. Not in Baja. Not in most places near the equator. So you could get on a plane and be somewhere sunny and warm in a few hours. You could look at cheap flights to warm places and plan your getaway accordingly.
If that’s your main goal, be flexible and you could find a terrific deal. If you don’t have your heart set on one certain place, you can see where the bargains are and use that as a guide.
How to find cheap flights to warm places from your city
Finding great flight deals is far easier than it used to be for the average traveler, but if you want to let someone else do all the research, that’s an option too. Join up with Going.com (formerly the better-named Scott’s Cheap Flights) and they’ll alert you on deals from your own airport in the USA.
If the hotels or Airbnb apartments are a bargain too—or you can find a good package deal—then you hit the purchase button and go on an adventure! With the right destination, you might even need to dig out your bathing suit and flip-flops.
There are different guides out there on where the cheap flights are each month of the year, so you can start there to get an idea of which destinations are on sale, but really the best bet is just to use the free tools at your fingertips to sleuth around for flight deals from your own airport.
In general, the routes with the most competition are going to show the lowest prices, so you’re more likely to find deals to Orlando, Tampa, Las Vegas, Puerto Vallarta, and Cancun than you are to some obscure island in the Caribbean.
Many Central American countries like Belize and Costa Rica have higher flight capacity in the winter than they do in the summer, so there are actually better deals in the high season sometimes. Because of heavy competition, flights to Colombia are often cheaper than anywhere else south of Mexico.
But overall trends don’t necessarily tell you what’s a deal from your airport. To drill down more on that you can check Skyscanner (leave the destination blank) or Google Flights, which has a handy map showing prices from your home airport.
On my phone I usually use Kayak because I like the interface and now they’ve added a “search from anywhere” function where you can specify how many stops you’ll put up with. It automatically puts in NYC so switch it to your city before searching.
Just remember that they always make you work at it to get rid of flights where the fees will double the price. It’s a huge bait-and-switch scam that all the flight sites and airlines are in on to make prices look cheaper than they really are.
Sample prices on cheap flights from the north
Since the following cities have temperatures below freezing as I write this, I’m going to use them as examples to show you what kind of deals are out there to escape the cold in winter. I pulled up mid-February, a few weeks from the date I’m writing this, for a round-trip flight returning a week after departure.
I used the search to anywhere functions of both Google Flights and Kayak, using the maps to see where the cheap flight deals were. On the latter, I unchecked the dreaded “basic economy” options, so these are all real flights with a seat selection on a legacy airline or a budget one adding a checked bag each way.
Here are some warm places you can get to for not a whole lot of money.
Cheap Boston Flights to Escape Winter
Tampa Bay $231
Ft. Lauderdale $184
San Antonio $276
Cancun $289 (Spirit with checked bag) to $436 (American main cabin)
Puerto Vallarta $415 on American w/carry-on
Costa Rica $380
Guatemala City $344
Escape from Toronto to Warm Places
Merida, Mexico $412
Puerto Vallarta $395
Los Cabos $431
Jamaica $295
Belize $408
Medellin $361
Cartagena $364
Ecuador $390
Portugal $525
Hawaii $423
From Minneapolis Ice to Tropical Sun
Tampa $288
Orlando $312
Miami $270
Phoenix $173 (Allegiant w/checked bag)
San Diego $226
Cancun $350
If you’re willing to fly on Frontier, Allegiant, or Sun Country, there are lots of deals to Florida. the Caribbean, Central America, and Colombia from Minneapolis. Just be advised you’ll pay extra fees for everything, including a carry-on bag. Here’s my take on going with just an underseat bag as a personal item if you can pull that off.
Keep in mind that all of the above are for a relatively spontaneous vacation booking—only a few weeks before departure. If you plan ahead a bit more, you can sometimes find even better deals.
Kayak says the ideal time to book for North America, South America, or the Caribbean is around one month ahead. For Central America they advise three months ahead. That seems a bit excessive to me, but if you are planning a distant vacation, take a look then and see how prices are panning out.
What about Asia and Africa flights?
Alas, it’s really difficult to find a cut-rate deal on a really long-haul flight. That’s part of the reason you’ll see far more Europeans in the Canary Islands or Phuket than you will North Americans—and why there are far fewer Europeans in western Mexico or Colombia.
If you’re going to be in the air for 12 hours, burning fuel that whole time in a jumbo jet, the airlines’ cost structure is much higher. It’s hard to find a sub-$600 flight from North America to Australia, New Zealand, southern Africa, or most of Asia.
So there are three strategies to use for long-haul flights: 1) Wait patiently for a rare sale. 2) Suck it up and pay. 3) Do some travel hacking and cash in frequent flier miles.
I’m a big fan of the third approach and when I took my family to Southeast Asia, we paid for most of our flights with mileage. When I went to Thailand on a business trip and my wife wanted to join me, we got her there by cashing in frequent flier miles. It’s also how I got down to Argentina and back three different times.
I’m sitting on enough miles on Delta right now that I could fly anywhere in the world and back (in economy class anyway). This was done through some flying, yes, but more from getting and using the right credit card.
Often the sign-up bonus alone from an airline card will give you enough points to fly to Asia or Africa. Or get one from Southwest and that can at least get you to a sunny place in Mexico or Central America. For more on that, see this post:
The Basic Strategy Guide to Free Flights and Hotel Rooms
Do you really want to fly to Asia and back for a short vacation though? It’s much better if you have 10 days or less to stick to a region where you won’t be struggling with jet lag. Otherwise the first two days there and the days after you get home may be days where your body is still trying to catch up and adjust.
It’s better to save the long-haul places for slow travel times or when you have the freedom to work from anywhere. There are plenty of warm places in your own hemisphere to choose from. For some you don’t even need to pull out your passport if you’re American.
Happy hunting, and enjoy the sunshine!
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