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Cheap, Easy Flights to Help You Escape the Winter Cold


For the sake of full transparency, this is a little bit of a self-serving story, because as a company based in the cold, dark north of Minnesota, the Thrifty Traveler team has sunny, warm escapes on the mind lately.

Luckily, our team of flight deal analysts at Thrifty Traveler Premium have successfully hunted down plenty of options to get you out of your parka and into a swimsuit this winter. One theme that we’ve noticed about the warm weather destinations we’re finding cheap flights to is how easy and convenient most of them are.

We’re not sending you on a long-haul odyssey to a far-flung island with these deals. Instead, with one or two quick flights, we can get you beachside for a few days, a long weekend, or a weeklong escape without much hassle, and without even having to dig out your passport in some cases.


Varadero beachVaradero beach


Some travelers love the piece together big, complicated trips. Some travelers like a headache-free nonstop flight and an all-inclusive. Most travelers are a little bit of both, and in this story, we’re going to focus on the latter.

As Jay-Z once said in his hit song “Song Cry”: “We used to use umbrellas to face the bad weather, now we travel first class to change the forecast.” Here are some of our easiest (and cheapest!) flight deals to help you change the forecast in 2024.


Cheap Flights to Florida

Nearly every U.S. airline flies to Florida, and that’s not a coincidence. It’s in demand – always has been and always will be. For travelers from the East Coast and the Midwest, a quick and easy Florida escape is a time-honored tradition.

Why? Because finding a cheap flight to one of Florida’s beaches isn’t too tall of a task.


Tampa Florida flight dealTampa Florida flight deal


This flight deal to Tampa (TPA) is a perfect example. Flying nonstop from many cities and with one quick connection from the rest, this deal could you have you beachside on the Gulf of Mexico the same day you fly out!


Nonstop to TampaNonstop to Tampa


On the other side of the state, facing the Atlantic Ocean, are the South Florida beaches of Miami (MIA) and Fort Lauderdale (FLL). Miami is a cultural hub of the U.S., offering travelers both big city trappings and a beachy, warm escape.


Miami Florida flight dealMiami Florida flight deal


Even more so than Tampa, Miami (MIA) and Fort Lauderdale (FLL) are both insanely well-connected hubs, allowing travelers from all over the U.S. and Canada a straight shot to South Beach.


Miami flight dealMiami flight deal


Cheap Flights to California

On the other side of the country, Southern California offers the same thing for West Coasters and Mountain West dwellers that Florida does for the East Coast: Cheap flights.

Los Angeles (LAX) is a quick and easy winter escape for most travelers on the left side of the map, offering picture-perfect weather almost any day of the year.


Los Angeles, California flight dealLos Angeles, California flight deal


Thankfully, LAX is a mega-hub airport, meaning dozens of airlines operate hundreds of routes to get you to the beach or the hills in no time.


Los Angeles flight dealLos Angeles flight deal


It’s still California and it still has the pristine weather, but Palm Springs is a much different trip than Los Angeles.

A laid-back pool day, a slow afternoon on the golf course, or a gentle hike in the mountains of Palm Springs offers a more unplugged, leisurely California vacation.


Palm Springs flight dealPalm Springs flight deal


Lately, flight prices to Palm Springs (PSP) have been stellar, including all of these sweet nonstop routes to the desert for a trip this winter.


Palm Springs flight dealPalm Springs flight deal


Passport-Free Island Escapes

The Caribbean is right on our front porch here in the U.S. We’re all lucky to have so many world-renowned destinations within six hours of flying for most Americans.

And for some of those islands, you don’t need to clear customs, get a visa, or even bring your passport to enter.


USVI flight dealUSVI flight deal


The U.S. Virgin Islands are one great example of this, offering a stress-free escape to a place that feels a world away, but with the convenience of getting off a flight that could’ve just landed in Cleveland instead.

We scour for St. Thomas (STT) deals like this one all the time, and we always send alerts when fares go down. We do the same for nearby St. Croix (STX), too.


St. Thomas flight dealSt. Thomas flight deal


Puerto Rico is in the same boat. A paradise of adventure, beaches, surf, and beautiful Caribbean weather is just a short flight away while your passport stays in the drawer back home.


Puerto Rico flight dealPuerto Rico flight deal


Flight prices to San Juan, Puerto Rico (SJU) have dipped in recent months, bottoming out with this $213 roundtrip fare from Pittsburgh (PIT) just last week!


PIT to SJU flight dealPIT to SJU flight deal


Cheap, Easy International Flights to the Dominican Republic and Mexico

If your passport is in good standing and you don’t mind using it, there are two more perfect warm-weather getaways right under our noses: The Dominican Republic and Mexico.


Dominican Republic flight dealDominican Republic flight deal


Punta Cana (PUJ) has long been a favorite of American travelers, and that hasn’t changed. The flight deals to PUJ are hit-or-miss, but this one hit…big time!


Dominican Republic flight deal infoDominican Republic flight deal info


From Ottawa (YOW) down to Lubbock, Texas (LBB), travelers all over the continent could take advantage of these fares to the beaches of the Dominican.

While Punta Cana flights typically require a connection somewhere, Cancún (CUN) flights seldom do.


Cancun flight dealCancun flight deal


This latest nonstop flight deal to Cancún was a sizzler, connecting airports all over the country to the Yucatan Peninsula without any layovers whatsoever!

When we sent this deal a few weeks ago, you could even book it for a trip over Christmas. Don’t worry: Santa will know where you find you.


Cancun flight dealCancun flight deal


Travelers love Cancún because of its luxurious all-inclusive resorts and its proximity to the town of Tulum. Just a 90-minute drive south of the CUN airport, Tulum has long been a favorite among travelers.

And now, Tulum lovers have an even better option: a Tulum Airport (TQO).


Tulum, Mexico flight dealTulum, Mexico flight deal


That’s right! Starting this April, U.S. airlines will be able to fly directly to Tulum (TQO), giving flyers a way around the long drive down. So far, American, Delta, Spirit, and United have all announced Tulum service, so it was only a matter of time until fares dropped.

And drop they did.


Tulum flight dealTulum flight deal


Use Your Points and Miles For a Winter Escape

If you’ve been stockpiling points and miles, stop! Our best advice for travelers is not to hoard points. They only get less valuable over time. Redemptions don’t need to be perfect, they just need to help you save money on travel.

And in some cases, a flight to the beach will barely put a dent in the points in your account anyway!


Southwest Rapid RewardsSouthwest Rapid Rewards


This sale from Southwest Airlines using Southwest Rapid Rewards points was a memorable one. In some cases, you only needed 6,000 points for a roundtrip (I repeat: roundtrip) flight to Mexico this winter.


Southwest Rapid Rewards dealSouthwest Rapid Rewards deal


You could easily transfer points from Chase to book, too.

Points and miles are phenomenal ways to book flights you otherwise couldn’t afford. That’s how I use my miles, and that’s where this amazing Key West, Florida (EYW) sweet spot comes in.


Key West, Florida flight dealKey West, Florida flight deal


Flights to Key West are normally around $500 or more roundtrip per person, but if you use American Airlines miles, those flights are priced just like any other domestic flight. That means 10,000-15,000 miles are all you need to book that dreamy Florida Keys getaway.


Key West, Florida flight dealKey West, Florida flight deal


Finally, we’ll let you in on one more special sweet spot: Booking Delta flights with Virgin points.


Virgin Delta nonstopsVirgin Delta nonstops


If you’ve read Thrifty Traveler before, you can probably tell we’re obsessed with this workaround for booking Delta flights, which can get pricey, especially to the Caribbean.

By transferring flexible points like Amex Membership Rewards, Chase Ultimate Rewards, or Capital One Venture Miles to Virgin Atlantic, you can book Delta nonstops at much cheaper rates. Even after a recent devaluation, it still worth saving your Delta SkyMiles and booking through Virgin for fewer points.


Virgin delta dealVirgin delta deal


This is just the list of flights from Atlanta (ATL), too. This works for hundreds and hundreds of Delta routes flying all over the world. Even after a recent devaluation, it’s still often a much better deal than booking directly through Delta.


Bottom Line

It might be getting cold outside, but cheap, easy flight deals to some of our favorite destinations are heating up!

You don’t have to fly across an ocean or break the bank to get out of the winter cold this year. Instead, choose travel on easy mode this winter and plan your escape now.



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