Panoramic view of Guatape from the Rock (La Piedra del Penol), near Medellin, Colombia.

10 Stylish—and Affordable!—Places to Fly This Winter

Winter is coming, and with it is a handful of holiday fares and warm-weather getaways. Spend Thanksgiving on the beach in Puerto Rico or ring in the New Year in Tokyo. No matter what your travel style is, from a safari in Tanzania to the sugary sands of Tahiti, there’s a destination deal for your next affordable winter vacation. Get packing!

Note: All prices were accurate when published, but are subject to availability.

Chelsea is Brooklyn-based travel writer, editor, and photographer. When not home eating her way through NYC, she's gallivanting across the globe, sailing the coast of Croatia or hiking the peaks of Peru. Her superpowers include booking flight deals and sleeping in small plane seats.

See recent posts by Chelsea Bengier

St. Thomas, USVI. Heavensight cruise ship dock in Charlotte Amelie.

St. Thomas, USVI

We always suggest escaping to the Caribbean during winter for some fun in the sun. This year, there are flights via Spirit, JetBlue, and United to St. Thomas starting at an insane price of $161 round-trip from Orlando, Fort Lauderdale, New York, Washington, D.C., Dallas, Boston, Dallas, Los Angeles, and Chicago. You must travel before Christmas though, as fares skyrocket during the holidays.

See flight deals to St. Thomas (STT) via Airfarewatchdog >

Book Hotels in the U.S. Virgin Islands


All eyes are on Tokyo for the 2020 Summer Olympics, but if you want to get a preview of the Japanese city before the crowds descend, there's no better time than now: we found flights to Narita International Airport in January for as low as $560 round-trip from Philadelphia, New York City, and Miami. Can't swing a January departure? Impossibly, there are also fare drops in April, during cherry blossom season.

See flight deals to Tokyo (NRT) via Airfarewatchdog >

RELATED: JS Travel Diaries 2019: Just Back from Japan

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'A small group of African Elephants in different ages is moving in the plains of Serengeti.Location: Serengeti National Park, Tanzania. Shot in wildlife.'


It is extremely rare for far-flung destinations like Dar es Salaam, a coastal city in Tanzania and an excellent jumping-off point for those wanting to see the Big Five on a safari in the Serengeti, to be affordable. However, if you book now, it'll only cost around $600 round-trip—half off the typical ticket—from Atlanta, Denver, New York City, or San Francisco.

See flight deals to Tanzania (DAR) via Airfarewatchdog >

Book Hotels in Tanzania


Hop across the pond to the city of canals for a bargain-bin rate of $450 round-trip. This is one of this season's best deals because there are flights from almost every state (and even smaller, regional airports like Allentown, Aspen, Destin, Kauai, Mobile, Rochester, etc.). Search basic economy seats on American and United for travel between November (including Turkey Day) and March.

See flight deals to Amsterdam (AMS) via Airfarewatchdog >

Book Hotels in Amsterdam
Volcan Arenal rises out of the jungle and dominates the landscape near the town of La Fortuna, Costa Rica.

Costa Rica

Adventure junkies should make a beeline for this Central American country, whose hot springs are the perfect antidote after all that rainforest canopy walking, waterfall rappelling, and horseback riding. All major U.S. carriers can send you to San José for as low as $206 from cities such as Atlanta, Boston, Chicago, Houston, Las Vegas, New Orleans, Providence, Cleveland, Tampa, and New York City, among others. Dates are scattered by the departure point, but we found the best availability in October, November, and January. Note: Copa also has cheap rates, but those come with the possibility of a long layover in Panama.

See flight deals to Costa Rica (SJO) via Airfarewatchdog >

Book Hotels in Costa Rica


If you’re based in San Francisco, then Tahiti should be your next exotic escape. Just picture black-sand beaches, overwater bungalows, crystalline lagoons. Tickets usually charge more than a grand, but are currently clocking it at $525 for dates between November and January. The caveat: you’ll be using budget carriers French Bee or Air Caraïbes, so you’re not likely to rack up any frequent flyer points.

See flight deals to Tahiti (PPT) via Airfarewatchdog >

RELATED: Island-Hopping in French Polynesia: What to See in Bora Bora, Moorea, and Tahiti

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Puerto Rico

This is one of the most flexible deals we’ve seen for the winter. JetBlue is offering multiple round-trip routes from almost every major airport to San Juan through February at around $150 to $300. Alternatively, you can skip around the country by flying into San Juan and out of a different airport like Ponce or Aguadilla (on the western side of the island, close to Rincon—a famed surf spot). Bonus: some airlines, such as American, Delta, and United, are also offering Thanksgiving sales from certain cities.

See flight deals to Puerto Rico (SJU) via Airfarewatchdog >

Book Hotels in Puerto Rico

Buenos Aires

In the cold winter months, head down to the southern hemisphere, where it’s summertime in Argentina. This tango town is seeing discounts on seats from New York City and Los Angeles, beginning in the $500 range for round-trip reservations between October and February 2020.

See flight deals to Buenos Aires (EZE) via Airfarewatchdog >

Book Hotels in Buenos Aires
Kuala Lumpur skyline overlook, Malaysia

Kuala Lumpur

The capital of Malaysia isn’t often on sale, so snag it while you can. The great part is that because Kuala Lumpur has affordable access to nearby destinations such as Bali, Singapore, and Bangkok, you can even extend your stay and see more of Asia. The best way to get there is via United or ANA from New York City (all three major airports), Seattle, and Chicago for $475 round-trip.

See flight deals to Kuala Lumpur (KUL) via Airfarewatchdog >

Book Hotels in Kuala Lumpur


Between coastal Cartagena and mountainside Medellín, Colombia has a little bit of something for everyone. You’ll find the most routes to the capital of Bogotá (starting at $344) as well as a few to Cartagena from Atlanta, Chicago, New York City, Philadelphia, and most major cities in Florida. Medellín, meanwhile, is rarer with only two options from New Orleans and Portland, Maine. You’ll have the most luck searching on Avianca, Copa, JetBlue, and American.

See flight deals to Bogotá (BOG) via Airfarewatchdog >

See flight deals to Cartagena (CTG) via Airfarewatchdog >

Book Hotels in Colombia

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