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Top 7 Cheapest Warm Weather Getaways For Americans To Fly To This Winter

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Americans are getting ready to fly to warm-weather locations with tropical beaches and rich cultural experiences.

Fortunately, you don’t have to break the bank to find yourself cozying up to a cocktail on a white sand beach this winter, as there are 7 warm weather getaways that are cheap to fly to this winter.

According to a new Skyscanner report, Americans are looking for value as much as time in the sun or cultural experiences.

San Juan Puerto Rico travel happy Asian tourist woman excited with open arms in happiness at watch tower of Castillo San Felipe del Morro summer cruise vacation.

However, the study also says that 39% of American travelers are planning on spending more on travel in 2024 than in 2023. While that may sound shocking, considering that value was ranked as more important, Americans are looking to save on things like food, flights, and rental cars.

This means more money will go towards experiences, lodging, and finding their dream destination. 

According to Skyscanner, these are the top 7 cheapest destinations for Americans to fly to this winter.

San Juan, Puerto Rico

This beautiful Caribbean island is a U.S. territory, and Americans can find round-trip flights here for as low as $295. For American travelers looking for a deal, nothing beats Puerto Rico. 

However, the island is way more than just a cheap and close getaway for Americans. With its rich culture, stunning nature, delicious cuisine, and endless tropical beaches, it’s no wonder why it’s such a popular destination. 

Its largest city, San Juan, has plenty of historical charm and endless nightlife. However, the island’s off-path locations, such as beach towns like Arecibo and local hangouts such as Cabo Rojo, are also attracting visitors. 

colorful buildings dot the coast of San Juan Puerto Rico

Nassau, Bahamas

The Bahamas sit just over 100 miles off the coast of Florida and are world-renowned for their pristine tropical beaches, coral reefs, and welcoming culture. For Americans looking for an affordable warm-weather destination that’s close to the US, it’s hard to beat the Bahamas. 

Now, Americans can fly round trip to Nassau, the capital and largest city of the Bahamas, for $347. The city is not only the gateway to the islands, their beaches, and resorts, but a culturally rich destination worth experiencing. 

On top of being a budget-friendly tropical getaway, the islands are served by even more routes this year. JetBlue, Alaska Airlines, and Delta have all increased their amount of direct flights between major U.S. cities and Nassau. 

A view of Nassau Bahamas Lighthouse where JetBlue will soon fly

Cancun, Mexico

Mexico’s tropical Yucatan Peninsula has been a hotspot for American travelers this year. No matter if you’re looking for beachside, all-inclusive experiences or hiking through Mayan ruins, this destination is like nowhere else on earth.

It’s also very affordable, with airfare running around $422 round trip. This winter, Americans can fly directly to Cancun at incredibly good rates. 

Once you’re there, you can set off on the Maya Train, which will launch just in time for winter. You can board the Maya Train in Cancun and travel to UNESCO World Heritage Sites like Chichen Itza and bucket list destinations like Tulum. 

Cancun Viewed From Above

San José del Cabo, Mexico

On the tip of Mexico’s Baja Peninsula is the small city of San José del Cabo. This beautiful destination is popular for its white sandy beaches and for being the international airport serving Cabo San Lucas.

Americans can fly here and back for only $429, making it one of the most affordable warm-weather destinations. Once you're here, you can either take a bus to Cabo San Lucas or rent a car to explore the beautiful region.

Cabo San Lucas and southern Baja are famous for their incredible surf, scuba diving, and notoriously fun nightlife. Plus, it has some of the most tourists in the country, making it an easy and stress-free place to spend your downtime.

Panoramic View Of A Beach In Cabo San Lucas, Los Cabos, Baja California Sur, Mexican Pacific, Mexico

Bogota, Colombia

Colombia’s capital and largest city has some of the cheapest airfares to South America for Americans. For only $440, Americans can fly round trip to Bogota, and once you’re there, you can easily fly to many other top destinations in the region. 

Aside from being a major hub for international flights, Bogota is a city full of culture and nightlife. Travelers and digital nomads love this city for its welcoming people and non-stop energy. 

Although Bogota has cooler weather because of its high-mountain location, it’s not far away from the beautiful beaches and steaming jungles Colombia is famous for. 

botero plazo bogota colombia

Puerto Vallarta, Mexico

Jalisco’s oceanside gem is a major hub for travelers looking for cultural experiences, world-famous cuisine, and endless warm-weather relaxation. Puerto Vallarta is also a safe destination with welcoming locals and year-round warm tropical weather. 

To get to Puerto Vallarta, Americans pay as little as $460 to fly directly from many major airports in the U.S.

This makes the city the perfect destination for Americans looking to experience the rich culture of Mexico affordably without flying to Cancun. 

Aerial View Of Puerto Vallarta, Jalisco, Mexico, Latin America

Santo Domingo, Dominican Republic

The Dominican Republic is booming this year for American travelers. It offers everything from rich culture and historical charm to some of the best beaches in the Caribbean. 

What’s more is that you can fly here from many major U.S. cities for around $460. While most of the island’s famous resorts are in the stunning coastal community of Punta Cana, the DR’s capital is well worth a visit. 

With incredible colonial architecture, diverse food scene, and friendly people, this is one of the most exciting capital cities in the Caribbean. Plus, it’s the home of Merengue and some of the most popular musical acts and nightclubs in Latin America.

Tourist woman appreciating the beauty of the colonial city of Santo Domingo, Dominican Republic

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