Cheap Flights to Warm Places When It’s Cold Outside

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.

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 deals are and use that as a guide. 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.

Kayak has a handy guide to 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. For January, they say Tampa and Las Vegas are the best values for the USA, Chiang Mai, Bali, and Oaxaca are cheaper than usual internationally.

For February, they highlight Puerto Escondido (one of the best beach bargains in Mexico) and the U.S. Virgin Islands as warm places on sale.

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.

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 the end of January, two weeks from the date I’m writing this, for a round-trip flight returning a week after departure. Here are some warm places you can get to for not a whole lot of money.

Cheap Boston Flights to Escape Winter

New Orleans $259 (or on Spirit $123)
Los Angeles $312
Cancun $290-$364 on American, United, Delta
Belize $301-$364 on American, United, Delta
Costa Rica $391
Cartagena $568
Morocco $522

Escape from Toronto to Warm Places

Merida, Mexico $311
Ixtapa/Zihuatanejo $354
Los Cabos $371
Jamaica $341
Belize $265-$314
Guatemala $383
Costa Rica $268-$336
Medellin $407
Ecuador $470
Portugal $445
Singapore $601

From Minneapolis Ice to Tropical Sun

New Orleans $118
Orlando $212
Miami $239
Puerto Rico $298-$375
Hawaii $554-$695
Cancun $401
Belize $604

* If you’re willing to fly on Spirit, 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.

Keep in mind that all of the above are for a relatively spontaneous vacation booking—only two 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.

Alas, it’s really difficult to find a cut-rate deal on a really long-haul flight. 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. I’m sitting on enough miles on American right now that I could fly anywhere in the world and back (in economy anyway). This was done through some flying, yes, but more from getting and using the right credit cards. For more on that, see this post:

The Basic Strategy Guide to Free Flights and Hotel Rooms

Happy hunting, and enjoy the sunshine!