Skip to Content

These 2 Trending Caribbean Islands Are The Cheapest For A Winter Getaway

Share The Article

Last Updated


Are you looking for the ultimate Caribbean getaway that won’t break the bank this winter?

These 2 trending islands are the cheapest in the Caribbean, and there are tons of deals on both flights and resorts to these destinations.

Punta Cana, Dominican Republic Areal view of Bavaro beach in Punta Cana, Dominican Republic

Jamaica and the Dominican Republic are both setting new tourism records this year.

More American travelers than ever before are flocking to both Jamaica and the Dominican Republic, and it’s not hard to see why. Both islands have some of the best beaches in the world, a variety of hotels and resorts for every budget, and are easily accessible from the United States.

Here’s what you need to know about planning a cheap getaway to Jamaica or the Dominican Republic this winter.

Aerial view of beach in Dominican Republic

Getting To Jamaica

There are nonstop flights from close to 20 cities in the United States to Montego Bay, Jamaica. This is the most common airport to fly into for visiting Jamaica, offering easy access to the tourist hotspots of Montego Bay, Negril, and Ocho Rios on the north coast of the country.

For Canadian travelers, there are 7 nonstop flights to Montego Bay from major cities across Canada, many on low-cost airlines.

Blue hole waterfall in Ocho Rios Jamaica

For Americans, budget carriers like Frontier Airlines are also launching new routes to Jamaica, making it easy to find a cost-friendly flight this winter.

According to Google Flights, here are some sample round-trip flights for this winter:

  • New York to Montego Bay in December on American Airlines: $380
  • Atlanta to Montego Bay in December on Frontier Airlines: $218
  • Toronto to Montego Bay in December on Canada Jetlines: $247
Aerial view of tropical Caribbean island of Montego Bay, Jamaica

Getting To The Dominican Republic

The Dominican Republic is another destination with many affordable flights from the United States and Canada. In fact, the country ranks as the cheapest country to fly to internationally.

The biggest airports in the Dominican Republic are located in Punta Cana, Santo Domingo, and Santiago. Which airport you choose depends on where you’re staying.

Secluded beach on Saona Island, La Romana, Dominican Republic

Punta Cana is by far the most popular tourist destination, with 17 direct flights from cities in the United States and 9 direct flights from cities in Canada.

According to Google Flights, here are some sample round-trip flights for this winter:

  • Chicago to Punta Cana in December on Frontier Airlines: $376
  • Orlando to Punta Cana in December on Spirit Airlines: $219
  • Toronto to Punta Cana in December on Flair Airlines: $209
Sunset in Punta Cana, DR

Resorts In Jamaica

In addition to cheap flights, Jamaica is also known for its affordable all-inclusive resorts.

All-inclusive resorts are popular because they offer a hassle-free vacation. The rate you pay includes your room, all food and drinks, and sometimes extras like airport transfers and water activities.

According to Booking.com, here’s the cheapest price for a couple staying at an all-inclusive resort in Montego Bay for one week this December:

  • Holiday Inn Resort Montego Bay All-Inclusive, an IHG Hotel: $1,436
  • SeaGarden Beach Resort – All Inclusive: $1,564
  • Deja Resort All Inclusive: $1,643

Between flights and a resort, it’s possible for a couple to have a week-long Jamaican vacation for as little as $1,000 per person this winter.

Montego Bay Jamaica pool with ocean in background

Resorts In The Dominican Republic

The Dominican Republic is also home to numerous budget-friendly all-inclusive resorts.

Staying in an all-inclusive resort in the Dominican Republic is a great way to have a relaxing vacation where you don’t have to worry about a single thing.

According to Booking.com, here’s the cheapest price for a couple staying at an all-inclusive resort in Punta Cana for one week this December:

  • Impressive Premium Punta Cana – All Inclusive: $1,278
  • Catalonia Punta Cana – All Inclusive: $1,475
  • Catalonia Royal Bavaro – All Inclusive – Adults Only: $1,656

As you can tell, the Dominican Republic is another destination where it’s possible to spend as little as $1,000 per person on an affordable week-long getaway.

Beach vacation and travel background. Aerial drone view of beautiful atlantic tropical beach with straw umbrellas, palms and boats. Bavaro beach, Punta Cana, Dominican Republic

Read More:

Top 5 Travel Insurance Plans Starting At $10 Per Week

How To Easily Earn Points For Free Travel

↓ Join Our Community ↓

The Travel Off Path Community FB group has all the latest reopening news, conversations, and Q&A’s happening daily! 

Travel-off-Path-group-1-1
SUBSCRIBE TO OUR LATEST POSTS

Enter your email address to subscribe to Travel Off Path’s latest breaking travel news, straight to your inbox.

This article originally appeared on TravelOffPath.com