New Year, New Travel Goals: Here’s Where To Travel In January For Less Than $500 Round Trip

Condado Beach San Juan Puerto Rico
Condado Beach San Juan Puerto Rico

It’s a new year, which means new travel goals. There’s no better way to set the tone in the new year than by starting with a vacation.

A recent YouGov study shows people are prioritizing their happiness in 2024, with Traveling as a top New Year’s resolution. What’s excellent about January is it’s officially the start of the post-holiday season. Many destinations are on sale until Spring Break begins in March. If you’re ready to hop on a flight, here’s where to travel this January for less than $500 round trip.

San Juan, Puerto Rico For Less Than $200 Round Trip

Castillo San Felipe del Morro in Old San Juan, Puerto, Rico
Photo credit: Parker Diakite

For travelers who need a break from January’s bitter cold temperatures, you will find sun and warmth in Puerto Rico. Even during its peak winter month, San Juan’s average temperatures hover in the 70s.

Keep in mind that many parties are happening in January. At the beginning of the month, Fiesta de los Reyes Magos, or “Three Kings Day,” is celebrated in Puerto Rico with parties and parades across the island. Another big day in January is Fiesta de la Calle San Sebastián, which officially ends the festive holiday season in Puerto Rico. It’s a street festival that honors Saint Sebastian in the Catholic faith. Celebrations are happening across multiple stages in Old San Juan. The streets are filled with local arts and live music during the day, followed by concerts and parties at night.

According to Skyscanner, flights from Fort Lauderdale, Philadelphia, Orlando, Tampa, Boston, Detroit, New York City, Chicago, Atlanta, Dallas, Fort Myers, Cleveland, Washington, D.C., Charlotte, and New Orleans can be purchased for less than $150 round trip.

The cheapest flight leaves from Miami, according to Expedia. Use January 17th through the 24th as your travel dates for a round-trip for less than $100.

Managua, Nicaragua For Less Than $200 Round Trip

colorful buildings in Leon, Nicaragua
Photo credit: Hermes Rivera

Nicaragua has two seasons: wet and dry. There’s no better time to visit this hidden gem destination in Central America than January because it’s the dry season and affordable. Known as “The Land of Lakes and Volcanoes,” Nicaragua has a backdrop that very few places rival with its natural beauty.

Nature lovers will find Nicaragua has a diverse landscape thanks to its volcanoes, lakes, and rivers.  It’s a playground for people who love spending time outdoors. Aside from exploring the outdoors, Nicaragua has a vibrant arts and culture scene outside its capital city, Managua.

Travel to Granada and Leon to explore the oldest cities in the Americas with unique architecture to explore.  Both towns have art galleries and crafts to purchase from local artisans.

According to Skyscanner, you can travel to Nicaragua for less than $200 round-trip from Miami, Fort Lauderdale, Charleston, Philadelphia, Chicago, Nashville, Boston, New Orleans, and Dallas this January.

The cheapest option is from Fort Lauderdale. Plug in January 16th through the 22nd into Expedia to purchase a round-trip ticket for less than $200.

Montego Bay, Jamaica For Less Than $300 Round Trip

Photo credit: Brighton Pereira
Photo credit: Brighton Pereira

Montego Bay is perfect year-round, but locals know snowbirds especially travel during the winter months to find solace, so January is an excellent time to travel to Montego Bay.

Montego Bay is hosting its annual Winter Xscape in mid-January. 2024 marks the 15th year of this event, which brings young professionals from all over the world to rest and “escape” from their busy lives. With its tagline of “Sometimes Happy Hour Isn’t Enough,” it’s an excellent event for relaxing, partying, and networking.

Round-trip flights from Fort Lauderdale, Philadelphia, Atlanta, Nashville, New Orleans, Memphis, Miami, Pittsburgh, Charlotte, Cleveland, Tampa, New York City, Dallas, and Chicago can be purchased for less than $300 round trip on Skyscanner.

Orlando is the cheapest city to fly to Montego Bay this January. Plug in January 27th through the 30th as your travel dates into Expedia to purchase a round-trip ticket for $201.

Port of Spain, Trinidad For Less Than $400 Round Trip

aerial view of Port of Spain in Trinidadq
Photo credit: LIAO XUN

Don’t miss this rare deal to Trinidad. According to Google Flights, the average round-trip flight to Port of Spain, Trinidad is around $645. Travel Noire found flights for nearly half of the price this January.

Once in Port of Spain, Trinidad’s largest and capital city, check out the National Museum and Arts Gallery. The national museum explores the island’s past and present through artifacts and exhibits.

A great way to relax in Trinidad is by visiting Maracas Beach. It’s a beach loved by locals and residents alike. One of the best parts of the beach is the drive to get there because the journey takes you through its iconic and scenic rainforest. Once there, you’ll be immersed in the landscape that Caribbean vacation dreams are made of, including blue waters, powdery sand, and coconut trees.

A trip to Trinidad isn’t complete without good food. The best way to try the best of the island is through a food tour to explore island favorites such as doubles, stewed chicken, oxtails, macaroni pies, and more.

According to Skyscanner, round-trip flights from Fort Lauderdale, Atlanta, Philadelphia, Washington, D.C., New York City, Charleston, South Carolina, Orlando, Chicago, Houston, Dallas, Charlotte, Las Vegas, Tampa, New Orleans, and Austin can be purchased for less than $450.

People leaving from Miami have the cheapest flight option, according to Expedia. Use January 18th through the 24th as your travel dates for a round-trip ticket priced at less than $280.

Mexico City, Mexico For Less Than $450 Round Trip

square in Mexico City - Best Urban Adventures in Latin America
Photo Credit: John Coletti

Mexico City is the perfect destination for people looking to explore a different side of Mexico outside of the ever-so-popular Cancun, Tulum, and Cabo. Mexico City is the capital of the Aztec empire, so it’s home to various cultural and historical sites.

While one of the new seven world wonders, Chichen Itza, is located near Mexico’s Yucatán Peninsula and provides insight into the Mayans’ wealth of knowledge, the ruins near Mexico City highlight another influential Mesoamerican civilization: The Aztecs. The towering pyramids known as the Temple of the Moon and the Temple of the Sun are the best places to witness Aztec history up close.

For culture lovers, the Condesa, Roma, and Nápoles neighborhoods are best for exploring cafes, art, music, and more.

This January, people leaving from San Antonio, Chicago, Dallas, Los Angeles, Miami, Orlando, Denver, and Fort Lauderdale can travel to Mexico City for $350 round trip or less, according to Skyscanner.

The cheapest flight leaves from Houston. Use January 16th through the 22nd as your travel dates in Expedia for a round trip for less than $290.

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