7 Cheapest Caribbean Islands to Fly to

by Jon Miksis
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Are you dreaming of a tropical escape to the Caribbean? While it’s easy to think flight tickets to paradise can be expensive, that’s not always the case. Knowing the secrets to great airfare deals makes it easy to find the cheapest Caribbean islands to fly to. That way, you can book an unforgettable (and affordable) trip of a lifetime.

As a frequent flier and world traveler, I know the ins and outs of travel deals and budget-friendly dream destinations. That’s why I’ve put together this helpful guide pointing you toward the cheapest places to fly to in the Caribbean!

The Caribbean is a massive archipelago (a group of islands) in the Caribbean Sea. It’s a popular destination for cruises, honeymoons, and family vacations, thanks to the friendly, laid-back culture and beautiful terrains and topographies. From shimmering turquoise waters and white sand beaches to tropical rainforests, the Caribbean is home to some of the most beautiful islands in the world. With so much to see and do, there is no such thing as a boring Caribbean vacation! 

Each Caribbean island has its own unique culture, incredible scenery, and delicious local cuisine. And while the climate varies, most islands enjoy sunny, warm weather throughout the year. This means that every time is a good time for a Caribbean vacation. Ready to plan your next tropical escape? 

Grab your SPF and sunglasses, and check out some of the cheapest Caribbean islands to fly to!

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My #1 tip for finding the cheapest flights to the Caribbean

Want to know how to find the cheapest flights to the Caribbean? Before getting into my recommendations for cities with the cheapest airports in the Caribbean, I want to share a quick tip on saving money on airfare.

For the past 3 years, I’ve been using Scott’s Cheap Flights (now called Going) to find cheap flights to the Caribbean from the US. Last year alone, I saved THOUSANDS of dollars on airfare. This includes a trip from Boston to Puerto Rico for only a $146 roundtrip fare. On average, I save over $350 roundtrip on transatlantic flights and $200 on domestic ones from their email alerts.

Don’t take my word for it, though; try it yourself. All you have to do is type in your preferred departure airport and your dream destination, and they’ll send mistake fares and other cheap flight deals directly to your inbox for FREE!

However, if you’re a frequent traveler like me and plan to fly more than once this year, consider upgrading to a premium membership for just $49 a month. In my experience, it pays for itself after your first flight (several times over).

Best of all, if you use my discount code Jon20 to save 20% when you join!

Considerations when looking for the cheapest Caribbean islands

Ready to explore the picturesque beaches of Montego Bay? Maybe you’re looking to stay active by hiking the El Yunque Rainforest. To help you achieve your tropical travel goals, we’ve scoured data from major airports worldwide. We now bring you 7 of the cheapest flights to the Caribbean from the US.

It’s important to remember that many variables go into finding the cheapest flights, including which airports you’re departing from. To make it easier, I limited my search to only look at flights departing from major airports in the US, like Logan, JFK, and LAX. You have a better chance of finding amazing deals from larger airports with many flights and airlines. 

No matter where you’re departing, one thing is sure. The tropical destinations listed below are some of the best deals for anyone planning a Caribbean escape. More importantly, these aren’t just the cheapest tropical islands to visit. They’re also among the world’s most beautiful, enriching, and popular tourist hotspots.

Looking to save BIG on airfare? I recommend signing up for Dollar Flight Club. Thanks to DFC, I saved $5,000+ on travel in 2023…so I couldn’t recommend it more!

Cheapest Caribbean places to fly to in 2023

Below are the cheapest flights to the Caribbean from the US and around the world:

1. Trinidad and Tobago

Trinidad and Tobago are a pair of islands just off the coast of Venezuela. If you’re looking for the cheapest Caribbean Islands to fly to, these twin islands should be on your list! These islands each offer unique experiences depending on what you’re looking for in a Caribbean vacation. Trinidad’s beauty comes from pristine mangrove swamps and rainforested hills. Tobago is more of your traditional Caribbean island, with palm trees and white sand beaches. 

The Island of Trinidad

Trinidad and Tobago is one of the cheapest Caribbean destinations
Trinidad is known for its boisterous carnival and bird species

The Piarco International Airport (POS) in Trinidad is the primary and cheapest airport to fly into Trinidad and Tobago. When you arrive, you can experience this Caribbean destination in two parts. The larger island of Trinidad hosts most of the nation’s largest cities and is best for experiencing the Port of Spain nightlife. It is also home to an annual Carnival celebration considered one of the greatest shows on Earth. This festival is like a 48-hour street party, known for its colorful costumes and exuberant celebrations. Other popular Trinidad tourist attractions are the Caroni Bird Sanctuary and the Lopinot Historical Complex, a former cocoa estate now a museum. 

The Island of Tobago

The smaller island of Tobago has beautiful beaches and cheap flights
Tobago is known for its beautiful coastline and beaches

While Trinidad has much to do and see, the smaller Tobago is a more idyllic tourist destination with a tropical rainforest reserve in the north. The uninhabited Little Tobago Island and Main Ridge Forest Reserve are top locations for viewing the county’s famous hummingbirds. Tobago also has its own airport, the ANR Robinson International Airport, within walking distance of several beaches. There are several exciting destinations on Tobago, such as Fort King George, a 1700s-era Fort with cannons and intact barracks. Tobago also has a coral reef which can be viewed via a glass-bottom boat tour, and Argyle Falls, a 54-meter tiered waterfall.

Whether you’re looking to party at Carnival or enjoy the quiet, pristine beaches, Trinidad and Tobago is a great island destination. It’s certainly a cheapest Caribbean island to visit.

2. The Bahamas

When it comes to planning a cheap Caribbean vacation, the Bahamas is a hotspot destination. This series of islands north of Cuba is known for their size and diversity. Whether looking for a relaxing tropical escape or a heart-pounding adventure, you can find it across 100,000 square miles of the world’s clearest ocean. 

Visit Exumas to swim with pig in the Caribbean sea
Visit Pig Beach on Big Major Cay to swim with the famous pigs

Most activities in the islands of the Bahamas are water-based. This includes fishing, boating, wildlife activities (like dolphin excursions), and underwater activities like snorkeling. One of the most popular activities is swimming with pigs in Nassau or The Exumas!

The Bahamas is an international vacation hotspot 

If you want to enjoy an all-inclusive vacation after booking a cheap flight to the Caribbean, you’re in the right place. There is a heavy resort presence in The Bahamas with many on-site activities. The Atlantis Paradise Island resort in Nassau is one of the most famous in the world. Nassau also has a famous beach called Cable Beach and a natural park with ancient ruins called Clifton Heritage National Park. Another notable beach is the famous Pink Sand Beach on Harbour Island, known for its unique color. 

For the cheapest Bahamas vacation, try the seafood! Seafood is a staple of the Bahamian diet, particularly Conch (pronounced “Conk”), a kind of mollusk. It is often served deep-fried. Other island activities include scenic golfing, gambling in various casinos, the Pirates of Nassau Museum, and the Garden of the Groves

The Bahamas is one of the cheapest Caribbean islands to fly to
Abaco is the boating capital of the Bahamas

The Bahamas is one of the cheapest Caribbean islands to fly to. There is an airport on each of its 29 islands, although the cheapest airport in the Bahamas is the Lynden Pindling International Airport (NAS), formerly known as Nassau International Airport. It’s the largest airport in the country, with 22 airlines with direct flights to the Bahamas. For the best airfare prices, the cheapest time to fly to The Bahamas is in September. It’s no wonder this is one of the cheapest Caribbean islands in 2023.

3. The Dominican Republic

Of all the Caribbean Island vacation destinations, many modern travelers choose the Dominican Republic. For one, vacationers love its paradisiacal beaches with white sands and turquoise waters. It has also become popular because it’s one of the cheapest Caribbean islands to fly to.

The Dominican Republic is one of the cheapest islands in the Caribbean
The Dominican Republic is one of the most popular islands in the Caribbean

When flying into the Dominican Republic, there are three main airports: Punta Cana International (PUJ), Las Américas International (SDQ), and Puerto Plata International (POP). When looking for the cheapest airports in the Caribbean, fly into Santo Domingo via Las Américas. Santo Domingo is also currently the cheapest city to visit in the Dominican Republic. However, Punta Cana is the busiest airport in the country, and you can find many flight deals. 

One of the biggest highlights when visiting the Dominican Republic is its food. You can dine on plenty of seafood, fresh, tropical fruits, and popular street food, such as empanadas and yucca balls. While you enjoy the cuisine, be sure to visit the Colonial Quarter for premier shopping. 

Some of the most popular activities around the Dominican Republic include Kayak Limon (a Lagoon kayaking tour), Liveaboard diving trips, and weekly carnivals and festivals in February. There is a famous blue lagoon inside a limestone cave known as The Three Eyes

You can take a hike to El Limon waterfall in Dominican Republic
El Limón waterfall in Dominican Republic

If you are interested in resorts, visit Bavaro Beach. This beautiful white sand beach has several resorts spread along its banks. Another community and tourist resort is Cap Cana, featuring world-class golf courses designed by Jack Nicklaus, luxurious five-star hotels, and miles of pristine white beaches. While you can enjoy the beaches and many golf courses year-round, the most popular time to visit is between December and April. 

4. Puerto Rico

Puerto Rico is a popular vacation destination and one of the cheapest places to fly to in the Caribbean and the world. While a smaller island than most, this country/U.S. territory has three international airports. The Luis Muñoz Marín International Airport (SJU) in San Juan is the largest airport in Puerto Rico and one of the cheapest airports in the Caribbean. Many large airlines fly to San Juan, including Delta, American Airlines, United, and JetBlue. 

Puerto Rico is a popular vacation destination and one of the cheapest Caribbean islands to fly to
La Chiva Beach “Blue Beach” in Vieques, Puerto Rico

Upon arriving in Puerto Rico, one of the most popular activities is taking a stroll along Flamenco Beach. As one of the top-rated beaches in the world, it is known for its picturesque white sand and turquoise waters. To enjoy the water, you can spearfish, snorkel, or take a night boating tour of the bioluminescent bays near Fajardo and Vieques

Puerto Rico is one of the cheapest Caribbean islands to fly to

If you are a fan of rum, a great experience is the Casa BacardÍ, a historic BacardÍ distillery with tours. For a day trip, you can visit the small scenic island of Cayo Icacos off the island’s eastern side. It is surrounded by clear blue waters teeming with fish and underwater life, making it an ideal snorkeling spot. 

Puerto Rico is a beautiful country with beautiful beaches and waterfalls
The Chorro de Dona Juana Waterfall is a roadside stop and swimming hole in the Cordillera Central Mountains

Puerto Rico also possesses many historical monuments and ancient structures for visitors to learn about the culture. Fort San Cristóbal, the largest fort built in the new world by the Spanish, is a Unesco World Heritage site. Another fort worth visiting is the San Juan National Historic Site

Perhaps the most interesting attraction, however, is El Yunque, Puerto Rico’s rainforest. The forest contains extremely dense and beautiful plant life, walking trails, and exotic and endangered species. Whether you want to explore the rainforest, snorkel off the coast, or relax on the beach, Puerto Rico is an ideal destination. With so many cheap Caribbean flights, it’s a no-brainer to visit!

5. St. Thomas

The Virgin Islands remain one of the most popular destinations in the Caribbean. And when it comes to affordability, St. Thomas remains one of the cheapest Caribbean islands to fly to. There is one airport on the island, Cyril E. King Airport (STT), and the most popular resorts and destinations can be reached easily by taxi or inter-island ferry. 

Charlotte Amalie is the largest city in St. Thomas and is a popular port for Caribbean cruise ships.
Charlotte Amalie Harbor in St. Thomas

Charlotte Amalie is the largest city in St. Thomas and is a popular port for Caribbean cruise ships. There are many vantage points and resorts to view the Charlotte Amalie Harbor, which can be a great view, especially if it is crowded with boats and cruise ships. The natural deep-water harbor here is the most active in the Caribbean.

St.Thomas’s primary draw is the massive sprawl of shops, especially at St. John Brewers on the Waterfront. The island is also known for its beautiful beaches, including Magens Bay Beach, a famous crescent-shaped white sand beach. Water Island, located across Charlotte Amalie Harbor, is another popular tourist destination. Pirates used to visit this island frequently to restore their freshwater reserves.

St. Thomas is a beautiful island and is one of the cheapest places to fly to in the Caribbean
St. Thomas is known for its beautiful beaches

For families visiting the Virgin Islands, Coral World Ocean Park is a must! It has many underwater animal swimming experiences and is fun for the whole family. Located right next to this park is the scenic Coki Beach, a popular beach among visitors. St.Thomas is also one of the cheapest golf destinations, with three scenic golf courses on the island. If you wish to check out what the other Virgin Islands offer, a ferry service runs between all three.

6. Aruba is one of the best cheap Caribbean islands to fly to

Cheapest Caribbean islands come in all shapes and sizes, and this is among the best known!

Just off the coast of Venezuela is one of the smallest Caribbean islands: Aruba. Despite its small size and singular international airport (Queen Beatrix International Airport), there is much to do and see here. For instance, Aruba is home to many famous beaches and natural water formations.

Aruba is one of the cheapest destinations in the Caribbean
Aruba is a beautiful island with famous beaches and wildlife

Two well-known and unique beaches are the Conchi Natural Pool and Baby Beach. Aruba’s other claim to fame is its natural bridges, rock formations carved by waves over thousands of years. 

The island is also home to several ancient buildings which can be toured from the island’s gold rush era, such as the Bushiribana Gold Mill and smelting station. Aruba is also home to the Antilla shipwreck, one of the largest shipwrecks in the world. Another popular destination is Arikok National Park, which has lava, quartz diorite, and limestone formations.

Arikok National Park is a popular destination in Aruba
Arikok National Park in Aruba comprises almost 20% of the island

For those interested in wildlife, there are several attractions worth visiting. There is the Butterfly Farm, a free-flying butterfly sanctuary where they will also teach you to attract butterflies to your own garden. If you are interested in larger animals, there is the Donkey Sanctuary, with over one hundred free-roaming donkeys, and an ostrich farm where you can learn how ostriches are raised. 

7. Jamaica

When looking for the cheapest Caribbean getaway, you can’t go wrong with Jamaica. It is one of the cheapest Caribbean Islands to fly to, with affordable accommodations. Even if you aren’t a Reggae fan, visiting the Bob Marley Museum is a must; Marley is undoubtedly Jamaica’s biggest icon. 

Jamaica is one of the cheapest Caribbean islands to fly to right now
Ocho Rios, Jamaica, is home to luxury plazas and world-class shopping opportunities

When visiting the island, there is a wide variety of uniquely Jamaican foods to try. They are known for their national dish, Ackee and Saltfish, and Jerk seasoned foods, the most popular of which is Jerk chicken. While Jamaican food has many meaty staples, vegans and vegetarians can enjoy Ital foods. This unique style of food is often celebrated by those in the Rastafari movement and is made with no processed ingredients.

Jamaica is a cheap Caribbean destination

If you’re looking for some outdoor adventure, Jamaica’s forests are a great place to visit. Mystic Mountain is one of the top attractions in Ocho Rios, where you can explore the forest’s rich ecosystem and sparkling river streams. You can even enjoy the spectacular views via the SkyExplorer or drive through the rainforest on sleds with the Rainforest Bobsled Jamaica attraction. In addition to fun attractions, the Jamaican rainforests are also home to many unique and rare animals, such as the Homerus Swallowtail, the world’s largest butterfly. 

Jamaica also boasts many scenic beaches known for their unique views, such as Negril Beach and Doctor’s Cave Beach, perhaps the most famous in Jamaica. It also has many famous waterfalls, such as Dunn’s River Falls, YS Falls, and Reach Falls.

Ochos Rios Blue Hole in Jamaica
Ocho Rios Blue Hole is one of the most breathtaking attractions in Jamaica

Before catching a flight home from Jamaica’s cheapest airport, Sangster International Airport (MBJ), you can play golf at the White Witch Golf Course, famous for its water views. You can also visit Floyd’s Pelican Bar, a driftwood shack built directly above the water about one kilometer out to sea. Cheap flights to Caribbean can’t touch it!

Frequently asked questions (FAQ) about the cheapest Caribbean Islands to fly to

Need more help preparing for your big trip? Here are some of the most common questions I receive about finding the cheapest places to fly to in the Caribbean. 

What is the cheapest month to go to the Caribbean?

Because airfare prices are often dictated by supply and demand, the cheapest time to go to the Caribbean is during their low season. While it may vary from island to island, the low season typically falls between May and August. The overall cheapest month to fly to the Caribbean is June. 

The Caribbean low season coincides with the start of hurricane season, and there are generally fewer tourists. Since fewer people make travel arrangements during these months, airlines will often offer flight deals to encourage travel. The other plus of planning a Caribbean vacation during low season? Fewer people on the beaches and at other popular destinations! 

If you’re concerned about hurricanes, plan your trip at the start of the season. In May and June, the Gulf of Mexico is more likely to experience hurricanes than the Caribbean region. In any case, pack a light jacket in case it rains. 

To find the best flight deals, use websites like Skyscanner and Google Flights to compare airline prices to find the cheapest time to fly to the Caribbean. 

two pigs swimming in the ocean in the Bahamas
From swimming with pigs to hiking a rainforest, the Caribbean has so much to offer

Where is the cheapest Caribbean island to fly to?

The Dominican Republic is the cheapest Caribbean island to fly to and visit when considering both airfare and accommodations. Regarding airfare, I’ve found roundtrip flights from Boston to Punta Cana for under $400. If you’re flying out of NYC, you can even find roundtrip flights for under $300.

The Dominican Republic also has much to offer in terms of accommodation options, ranging from luxury resorts to low-key hotels. The major areas like Punta Cana, Samana, Puerto Plata, and Romana are the best bets for finding deals on hotels. 

The best part about visiting the Dominican Republic is that it doesn’t feel like a cheap Caribbean vacation. It’s a beautiful country that is as easy on the eyes as it is in the pocket. From swimming and snorkeling in the ocean to ziplining and hiking through the jungle, this gorgeous and affordable Caribbean destination has so much to do and see.

Which airlines fly to the Caribbean?

When planning a Caribbean vacation, you have two options for travel: cruise and flight. While Caribbean cruises are a popular way to enjoy these tropical islands, they’re not for everybody. The good news: flights to the Caribbean are very popular, and many international carriers serve the islands.

For European travel, large European airlines such as British Airways, KLM, and Air France all offer frequent service to the most popular Caribbean islands. 

From the US, major airlines such as American Airlines, Delta, JetBlue, and United fly to many of the islands daily. 

If you’re flying from the US, you can find direct flights to the Caribbean’s cheapest airports from many major cities. These include but are not limited to Boston, New York, Philadelphia, Chicago, Denver, Miami, Dallas, and Washington DC.

an overhead view of Tropical Island Beach in the Dominican Republic, one of the cheapest Caribbean islands to fly to
Tropical Island Beach in the Dominican Republic

What is the cheapest day to fly to the Caribbean?

If you’re dreaming of turquoise waters and palm-fringed beaches but don’t want your wallet to walk the plank, I’ve got some insider info for you. When it comes to sailing the skies to the Caribbean, midweek is when you will find cheap Caribbean flights.

Why, you ask? Well, many travelers prefer to start their tropical getaway at the weekend, which can push prices up. But if you can set sail on a Tuesday or Wednesday, you’re likely to find calmer financial seas ahead.

But remember, the cheapest day to fly can vary depending on your departure city, your specific Caribbean destination, and the time of year. Is this one of the top ways to find cheap flights to Caribbean? Absolutely!

How far in advance should I book a flight to the Caribbean?

When looking to book a cheap flight to the Caribbean, your timing could make or break a great deal. If you’re a spontaneous adventurer, you may have some luck finding last-minute deals on flights to the Bahamas or the Virgin Islands. However, the best way to fly to the Caribbean islands cheaply is to book your trip a few months in advance. 

Throughout my travels around the world, I have found that you can typically find the best deals on flights to the Caribbean and other destinations 2 to 6 months in advance. You’re more likely to find better deals, promotions, and discounts on a Caribbean vacation if you book in this timeframe. If you’re flexible on your travel details, I recommend signing up for Going and waiting to see what deals come your way. Think of it as practice for island life: no stress, just waiting for that perfect opportunity to arrive.

Which Caribbean island is least expensive to travel to?

Ah, the Caribbean, a kaleidoscope of islands each with its own unique charm. But which one offers the most bang for your buck? Drumroll, please… it’s often the Dominican Republic!

This cheapest Caribbean island is known for its stunning beaches, lush mountains, and vibrant culture. But what sets it apart is its affordability. With a range of accommodations from budget-friendly guesthouses to all-inclusive resorts, the Dominican Republic caters to travelers of all budgets.

Plus, it’s one of the larger Caribbean islands, which means more flights. More flights often equal more competitive prices, so you can save your doubloons for exploring everything the island has to offer, from the historic streets of Santo Domingo to the kite-surfing mecca of Cabarete.

For the cheapest Caribbean island to visit, add the DR to your wish list in 2023!

cheapest Caribbean islands to fly to text overlay of a caribbean island surrounded by water
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