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Panoramic view of Lima from Miraflores.
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Cheapest Places to Fly This Winter (2020)


Holiday travel is notoriously pricey. But if you’re heading somewhere outside of the late-December date window, there are usually great winter vacation deals to snag—even in warm-weather destinations. December, January, and February are the low season in many places, and are often the most underrated months to get away for a lot less.

Have your pick of sunny beaches and wintry wonderlands with these far-flung destinations that are surprisingly affordable compared to how much the journey cost just last year. Here are the cheapest places to fly for a winter vacation in 2019, according to airfare experts and pricing data.

Editor’s note: All prices are the average for one round-trip flight unless otherwise specified. Special thanks to SkyscannerKAYAKTravelocity, Scott’s Cheap Flights, and Airfarewatchdog (SmarterTravel’s sister site) for sharing pricing data and commentary.

Lima, Peru

Aerial view of miraflores town, cliff and the costa verde high way. in lima
Christian Vinces/Shutterstock

Looking for a fare war to capitalize on? Consider a winter vacation to the Peruvian capital for ceviche, art, and beaches. Getting there is made easy thanks to the many airline options fighting a giant Lima newcomer: Delta. According to Airfarewatchdog pricing data, Lima airfare is dipping as low as $540 round-trip this winter; 35 percent lower than the usual average.

“When Interjet launched its ‘ultralight’ fares back in July, it had some incredible deals to destinations all over Latin America,” Airfarewatchdog analyst Peter Thornton says. “This included $220 round-trip flights to Lima from nearly all of its U.S. gateways. Spirit Airlines is also flying to Lima daily this winter … This combined with the big shakeup in Latin America due to Delta buying a major stake in LATAM has caused several fare wars to the region. Flights are cheaper on all airlines, including Aeromexico, American, Avianca, Copa, Delta, and JetBlue.”

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Jackson Hole, Wyoming

Ski slopes in jackson hole with panorama of vintage houses.

If you’re more of a skier or snow lover, winter is one of the most beautiful times of year to see the national parks and monuments in and around Jackson Hole, Wyoming. And it’s a winter vacation that’s not only cheaper in winter, but also 19 percent cheaper to fly to this year, according to Travelocity data.

Jackson Hole is busiest in summer when school is out and families overwhelm the area, but it’s still lively in winter months for skiing and snowshoeing, and for the numerous luxury spas in the area (think mountain-ridge hot tubs and cozy cabin-style massage rooms), which are typically on sale outside of the holiday season. Travelocity data shows that January is the best time for savings.

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Coast-to-Coast U.S. Flights

Palm springs, california residential desert architecture stephanie braconnier
Stephanie Braconnier/Shutterstock

Domestic travel that’s still far-flung makes for an affordable winter vacation this year. West Coasters can head east for a winter wonderland, while East Coasters can take to sunny L.A. and Palm Springs for cheap thanks to cross-country flight deals during the low season: Alaska, American, Delta, JetBlue, and United are all offering consistent deals, Airfarewatchdog’s Thornton says. And data from Travelocity, Skyscanner, and KAYAK confirms the trend.

“In the past, we would occasionally see coast-to-coast flights dip below $200 round-trip for winter travel, but this was only a few short unadvertised sale periods in past years. This year, it seems prices are remaining fairly steady at $197 round-trip on several popular coast-to-coast routes for nonstop flights between January and early March. Think New York, Boston, and Washington, D.C. to/from San Francisco, L.A., and Seattle,” Thornton says.

Palm Springs is also in on the action, with airfares that are about 20 percent lower than usual, according to Travelocity data. Los Angeles fares are down 12 percent to about $250 round-trip, according to Skyscanner. And February is the cheapest time to go with fares as low as $216, according to KAYAK data.

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San Juan, Puerto Rico

Puerto rico - street of san juan

Snowbirds flocking to the Caribbean in winter months can find a steal in the colorful capital of Puerto Rico—which also happens to be a great jumping-off point for smaller islands like Vieques and Culebra. During January and February, after Three Kings Day celebrations have died down, median airfare to San Juan is around $300 round-trip, according to KAYAK pricing data. That’s about 10 percent lower than recent years.

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Southern and East Africa

Crossing zone - serengeti national park tanzania, africa

If your bucket list includes a safari, consider January or February for lower airfare than you might expect. Scott Keyes, Chief Flight Expert of Scott’s Cheap Flights,  agrees that winter vacations don’t have to be expensive, and says this year, African air hubs offer some of the best new options.

“Aside from three weeks around Christmas and New Year’s, winter is the cheapest time of year to fly, even if you’re traveling somewhere warm,” Keyes says. “Some of the biggest drops in airfare this upcoming winter compared to last year include Africa. Typically one of the most expensive places to fly to, airfare all over the continent has fallen in a big way recently. Whereas fares underneath $1,000 were rare last year, there have recently dropped as low as $550 round-trip to places like Tanzania, South Africa, and Kenya.”

Airfarewatchdog analyst Ricky Radka says that Kenya is a perfect winter vacation for its array of airlines and equatorial weather: “Flights to Nairobi have been hovering around the $550 price range for a while, and what better time to go than in January and February that fall into Kenya’s dry season?”

Skyscanner data concurs, showing that Nairobi airfare is down eight percent in February, to about a $950 round-trip average. Airlines KLM, Air France, Swiss, and Lufthansa are common servicers of the area, and Radka says that Qatar Airways’ weekly sales “regularly include Nairobi from one of its 10 U.S. destinations.”

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woman relaxing on wooden swing under tree tropical beach, koh lao lading island, andaman sea, krabi province, thailand

A beach-centric getaway in Southeast Asia is also surprisingly cheap in January and February, Airfarewatchdog’s Radka says. Skyscanner data shows that February airfare is averaging about $740 round-trip, which is five percent down from last year’s already cheap average; and fares on Airfarewatchdog are closer to 14 percent off this year, on average. December is the only month out of the period that isn’t showing a price drop.

“Southeast Asia, in general, has been seeing some great-unadvertised fare sales, mostly to Vietnam, Indonesia, and Malaysia, but the one that continually sees the most competitive fares is Thailand. Five-star rated by Skytrax, ANA is usually your best choice as it allows passengers to stop in Tokyo on the way for only $100 extra, and has top-notch service,” Radka says. “Flights from New York, DC, Houston, and Chicago (United hubs) generally have the best prices, roughly $520 to $600 round-trip to Bangkok, but other West Coast airports regularly get deals from other carriers like EVA and Asiana.”

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Rome, Italy

Ancient square in rome, italy winter

Post-Christmas culinary adventures in one of the world’s best food cities make for a surprisingly affordable winter vacation in 2020. Rome is seeing an impressive 26 percent price drop for February, according to Skyscanner data, with airfare averages at $511 round-trip for the month—a perfectly romantic Valentine’s getaway. January is also comparably on sale, with 22 percent off the average airfare, putting flying to the Italian capital at about $544 round-trip.

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Copenhagen, Denmark

In the storget street in central copenhagen, denmark

Embrace winter with the Danish hygge lifestyle in February, when Copenhagen airfare is a whopping 29 percent off, according to Skyscanner. Pricing data shows that the average winter airfare is about $477 in February, which is the cheapest time to go in the three-month period. The downward trend in Copenhagen airfare has been fairly consistent in recent years thanks to competition sparked by budget carrier Norwegian Air, which flies direct to Denmark from the U.S. along with traditional carriers SAS and Delta.

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Miami beach tourists couple walking in south beach, miami, florida.

Snowbirds take note: It’s becoming downright cheap to reach Florida from the East Coast. “The catch is the lowest fares are for midweek travel, although there are still some good deals for weekend travel,” Airfarewatchdog’s Thornton says. “This is likely due to even more competition from budget carriers than in the past: Both Spirit and Frontier have expanded service to Orlando, Tampa, Miami, Ft. Lauderdale, and Ft. Myers, and Allegiant has added flights to some other Florida airports as well. And now that JetBlue has introduced its version of Basic Economy, it is better positioned to compete on price with these ultra-low-cost carriers.”

Bottom line: It’s very common to find flights to Florida for less than $100 round-trip on Airfarewatchdog. And other sites are seeing the trend too: Ft. Myers airfares for January are down 31 percent year-over-year, according to Skyscanner data. The median January airfare to Ft. Myers is $156 round-trip, according to KAYAK.

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Istanbul, Turkey

View of the st. sophia cathedral at sunset.
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In late 2019, political turmoil once again hit the country that straddles Europe and the Middle East, but Turkey is still a popular travel destination for its coastal Aegean historic sites by way of its bustling capital of Istanbul—which is seeing December airfares trending downward six percent, according to Skyscanner. The average price is $853, according to Airfarewatchdog, with about half of departure airports seeing at least a 10 percent drop in airfare.

KLM, Delta, and Turkish Airlines regularly appear in sale fares to Istanbul on Airfarewatchdog. If a more off-the-beaten-path area of Turkey is more your speed, the coastal city of Izmir often sees comparable fare prices, and is closer to the area’s renowned wineries, olive vineyards, and coastal historic sites like ancient ruins of the Roman city of Ephesus.

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For more ideas, see The Top Travel Destinations for 2020.

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SmarterTravel’s Shannon McMahon writes about all things travel, and finds the cheapest places to fly each season in this updating story. Follow her adventures on Instagram @shanmcmahon.

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