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4 Cheap Winter Vacation Destinations For U.S. Travelers

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If you haven’t yet visited these cheap winter travel destinations, what are you waiting for?

You don’t have to travel far (or spend tons of money) for a remarkable getaway. Are you looking for somewhere new to go for a winter getaway? We calculated some of the cheapest flights from cities across the U.S. that you can travel to this winter.

Factoring in a combination of flight prices, accommodation, food prices and free things to do, here are some of the best cheap winter vacation destinations for U.S. travelers this year.

panoramic view of Carambola Beach, St.Croix, US Virgin Islands

Cheap Vacation Destinations To Travel To This Winter

From what to do and where to stay, here are our recommendations for your affordable vacation this winter.

San Juan, Puerto Rico

Travelers can get one-way tickets for less than $100. Direct flights to the cultural capital of the U.S. territory of Puerto Rico available from Fort Lauderdale, Philadelphia and more. You can also score cheap flights here from Miami, Atlanta, Chicago, Cincinnati, Dallas and other major cities in the U.S.

Get to know this U.S. territory in the Caribbean a little better this winter. Start by exploring the Old Town and the San Juan National Historical Site to learn about Puerto Rico's history.

Colorful house facades along a street in Old San Juan, Puerto Rico.

For a nature escape, head 25 miles east to the gorgeous El Yunque National Forest. You can get there by taking a tour from San Juan, which will allow you to explore the rainforests, waterfalls, caves and so much more. Puerto Rico is a cheaper winter travel option compared to other destinations in the Caribbean, but it still offers amazing experiences.

Don’t have your passport updated yet? No problem, U.S. citizens do not need a passport to visit Puerto Rico.

Three people walking on a path at El Yunque National Forest in Puerto Rico. El Yunque is the only tropical rainforest in the U.S. National Forest system

U.S. Virgin Islands

One-way flights to St. Croix Island can be found for less than $100 from Fort Lauderdale, Chicago, Washington DC, New York, Atlanta and more.

Another U.S. territory in the Caribbean, there are so many reasons why the U.S. Virgin Islands make for an affordable getaway in the winter months. This is the place to relax and immerse yourself in nature.

Visit the Salt River Bay National Historic Park and Ecological Preserve and experience the mango forests, coral reefs and more. History buffs will love the Christiansted National Historic Site, where you can explore some well-preserved structures from when the Danish conquered the islands from the 1700s until 1917.

For more information, see our guide on our top reasons to visit the U.S. Virgin Islands this winter.

woman in black bikini relaxing in a hammock at a tropical beach at Maho Bay, St.John, US Virgin Islands

Guadalajara, Mexico

Flights to Guadalajara from major U.S. cities cost between $100-200. There are direct flights from Los Angeles, Houston, Miami, Chicago, Las Vegas and Atlanta, just to name a few.

The capital city of Mexico’s Jalisco state, Guadalajara is lesser-known than Cancun or Puerto Vallarta, but still lots to offer any type of traveler. Guadalajara is an easy walkable city so you can wander the Centro Historico and the local markets for free.

Travelers will find plenty of cheap and delicious street food and colorful neighborhoods to explore. Jalisco is where all of Mexico’s tequila is made, so there are plenty of affordable tours to the tequila region from the capital.

Guadalajara Cathedral (Cathedral of the Assumption of Our Lady), Mexico, Guadalajara Cathedral.

Cartagena, Colombia

Flights to Cartagena go for less than $250 round-trip. Non-stop flights are available from Orlando and Fort Lauderdale and cheap flights can be found from Durham, New York, Philadelphia, Washington DC and more.

Where Latin America meets the Caribbean, Cartagena has a little something for everyone. It’s right along Colombia’s north coast, so there’s more Caribbean culture here than other destinations in South America.

Head to the neighborhood of Getsemani if you’re on a budget, as this area is more affordable than the Old Town. Here you’ll find endless choices for funky cafes, art, clubs and cheap boutique hotels. Go on a self-guided tour to explore the colorful murals scattered across the city, and pop into every coffee shop to sample some Colombian cafecito.

sunset in cartagena colombia

What Are The Entry Restrictions For U.S. Travelers?

At the time of writing, Colombia and Mexico don’t have any entry requirements for U.S. travelers. Remember to always double check for the latest travel restrictions before jetting off somewhere new this winter.

Puerto Rico Beach

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