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Cheap Flights to the Caribbean: 9 Islands, Starting at $52 Each Way

Caribbean Airports + Flying
by Matador Creators Oct 5, 2023

It seems like hotel, food, and travel prices in the last two years have gone through the roof, but that doesn’t mean budget flights to the Caribbean are a thing of the past — it just means you may need to be a bit more flexible with when and where you go.

Below are nine of the best places to visit in the Caribbean this year or next, along with some exceptionally cheap flight fares we found. Note that flight prices usually follow a pattern: they generally climb over time, then get cheaper within a month or two of take off. So it may look like the cheapest prices for destinations below are all coming up soon, but in reality, there’s probably a good chance you’ll be able to find a similar fare at multiple times throughout the year. So check prices frequently before you book.

Tips for finding cheap flights to the Caribbean:

  • Fly midweek: This one isn’t a surprise, but most flights are much cheaper if you do a midweek trip, or even something like Monday to Saturday. Trips that are Friday through Sunday, or Saturday to Saturday, will always be the most expensive
  • Be flexible: If your goal is to hang out on a beach for a few days, you can head to just about any Caribbean island. But you may be surprised to learn what some islands have to offer. For example, while Bonaire and Curaçao are known for scuba diving, you can actually find amazing scuba diving in St. Maarten. And yes, Cuba and Puerto Rico may be most known for salsa dancing, but you’ll find find plenty of lively dance nights at bars and clubs on Barbados.
  • Fly to a cheaper airport: You can save potentially hundreds of dollars but flying to a different airport and leaving from there. Many cheap flights to the Caribbean are least expensive from nearby airports like Miami and Atlanta. So if you can fly to one of those airports (which you often can on budget airlines for under $100), you may still have a huge net savings. Just be sure to give yourself enough time to go out and back into security (TSA Precheck can help).
  • Check multiple websites: Skyscanner is an excellent tool for comparing what months and days a flight is the least expensive, so we’ve included Skyscanner links below. However, Google Flights and Kayak Explore are also two useful tools for finding great deals on flights. So shop around if you’re super price-conscious.

We hope you love the flights and destinations we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a flight. Listed prices are accurate as of the time of publication.

Cheap flights to Aruba: from $52 each way

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Great deals on cheap flights to Aruba:

Aruba is an island in the southern Caribbean Sea, off the coast of Venezuela. It’s part of the group called the “ABC Islands,” along with the nearby islands of Curaçao and Bonaire. Of the three, Aruba is generally the least expensive and has the most variety for hotels, activities, and restaurants. It’s also known for beaches with powdery white sands and and some of the most crystal-clear water in the Caribbean, making it ideal for snorkeling. Eagle Beach is the largest beach on the island, and Palm Beach has plenty of places for everything from beachside cocktails to snorkel and kayak rentals.

And if you like national parks, look more into Aruba. It’s one of the best cheap flights to the Caribbean you can book to do on-land exploring, with a landscape adorned with cacti and divi-divi trees, shaped by centuries of trade winds. Arikok National Park showcases this rugged beauty, with hiking trails leading to natural wonders like the Fontein Cave and Natural Pool. Aruba also offers a taste of history in its capital, Oranjestad, where colorful Dutch colonial architecture stands proudly alongside modern boutiques and restaurants.

Slow season in Aruba is December to April, which makes that the cheapest time to visit. But you can visit year round, including in October, as Aruba is well removed from the region’s Hurricane Belt.

Taking a trip to Aruba?

Cheap flights to Puerto Rico: from $87 each way 

old town san juan cheap flights to the caribbean

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Great deals on cheap flights to San Juan:

Puerto Rico will forever be one of the most attractive cheap flights to the Caribbean for a few reasons: first, Americans don’t need a passport, so it’s an extremely easy last-minute destination. It’s also warm when the mainland US is quite chilly, and since the vast majority of people speak both English and Spanish, it’s a pretty easy place to visit for travelers just starting to step out of their comfort zones.

One of the defining features that sets Puerto Rico apart is its rich cultural heritage. Influenced by a fusion of Indigenous Taíno, Spanish, and African traditions, the island has a vibrant arts scene, lively music (salsa!), and tantalizing cuisine that reflect its diverse roots. It also has quite a lot of variety in terms of terrain and ecosystems, from pristine white-sand beaches to lush rainforests; specifically, El Yunque National Forest. You can also kayak in a bioluminescent bay, explore centuries-old historic forts, bar hop through historic San Juan, or go spelunking in Rio Camuy Cave Park.

But it’s not all about San Juan. You can head to the southern part of the island to Ponce, called the “Pearl of the South.” It’s the island’s second-biggest city and is a little less touristed, with tons of museums, great food, and the popular Hacienda Buena Vista Coffee Plantation. And if you want to surf (or just like sitting on sunny beaches), head to the lower key town of Aguadilla. It’s not overly touristy (yet).

If you want the convenience of visiting the States with the adventure (and great food) of visiting the Caribbean, you’ll want to book a cheap flight to Puerto Rico ASAP — and they’re pretty cheap.

Taking a trip to Puerto Rico?

Cheap flights to the US Virgin Islands: from $90 one way

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Great deals on cheap flights to the USVI:

It’s no secret that passport processing has been moving slowly recently, so if you’re still waiting on yours, head to the US Virgin Islands. It’s one of the best cheap flights to the Caribbean you can book where just a drivers license is enough, as the USVI is an unincorporated territory of the United States.

The main islands are St. Thomas, St. John, and St. Croix. Each of these islands boasts its own individual character and attractions. St. Thomas is the most populous and developed and known for its bustling capital, Charlotte Amalie, with a lively downtown districts and a busy marina and port. St. John, on the other hand, is renowned for its unspoiled natural beauty; Virgin Islands National Park covers much of the island. And St. Croix has the most history, with Danish colonial architecture in towns like Christiansted and Frederiksted, along with beautiful beaches.

The main airport is on St. Thomas, but in terms of travel between the islands, there are several convenient options available. Regular ferry services operate between St. Thomas and St. John, given their close proximity, making it relatively easy to explore both islands in a single trip. There are regular inter-island flights connecting the islands, too, providing a convenient way to move between them on one trip.

Taking a trip to the US Virgin Islands?

Cheap flights to the Dominican Republic: from $111 each way

cheap flights to the caribbean - punta cana beach

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Great deals on cheap flights to the DR:

The Dominican Republic, which shares Hispaniola Island with Haiti, is known as the “Birthplace of the New World.” If you’re looking for cheap flights to the Caribbean where you can enjoy the outdoors and take in historical sites, the DR is a good choice.

The historic capital, Santo Domingo, has a beautifully preserved colonial zone that holds the distinction of being a UNESCO World Heritage site. You can take walking tours past sites like the Columbus Lighthouse and the Alcazar de Colon, or spend the evening tasting cocktails at historical bars like Pat’e Palo European Brasserie. Supposedly, it was a pirate hangout in the 1600s.

You’ll find pristine beaches stretch along both the Atlantic Ocean and the Caribbean Sea. Punta Cana, on the eastern coast, is famous for reasonably priced and luxurious all-inclusive resorts, so it’s a great destination if you just want a quick and relaxing trip to a warm-weather island this winter. But other good beach destinations include Puerto Plata, Samaná, and La Romana.

Outdoor-focused travelers can check out rainforests, soaring mountains, and unique attractions like the Cordillera Central mountain range. Or you could hike Pico Duarte, the highest peak in the Caribbean. Also leave time to check out the El Limón waterfall in Samaná and Los Haitises National Park. Music and dance are integral to Dominican life, and visitors can explore the local music scene along Santo Domingo’s Malecón, with merengue and bachata bars easy to find. And traditional Dominican Republic dishes are delightful fusion of flavors, offering traditional dishes such as sancocho (spicy beef stew) and mangu (mashed plantains).

Peak season for tourism is December through April, when it tends to be the least rainy. But the rainy season (summer) also tends to be cheaper.

Taking a trip to the Dominican Republic?

Cheap flights to Jamaica: from $112 each way

jamaica cheap flights to the caribbean

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Great deals on cheap flights to Jamaica:

Jamaica’s culture and history is rooted in African slavery and European colonialism, resulting in a vibrant and distinctive culture unlike any other island in the Caribbean. More recently, Jamaica has become renowned for reggae music, and the legacy of legendary musician Bob Marley is deeply ingrained in the island’s identity. So it’s one of the best cheap flights to the Caribbean to book if you’re looking for a cultural, musical, and generally lively vacation.

However, the island offers a wide range of natural attractions, including dozens of waterfalls the world-famous Blue Mountains. You can also tour coffee plantations or visit Dunns River Falls, where they filmed the James Bond Movie “Dr. No.”

Jamaica is also known for mouthwatering cuisine, with dishes like like jerk chicken and ackee and saltfish. Jamaica also has an excellent street food culture and local markets, which add to the island’s culinary charm.

Most people start their trips in Kingston, the capital, with attractions like the Bob Marley Museum and the National Gallery of Jamaica. Montego Bay, known for its beautiful beaches and vibrant nightlife, is also a popular destination. Ocho Rios boasts attractions like Dunn’s River Falls and Mystic Mountain, while Negril is famous for its stunning Seven Mile Beach and breathtaking sunsets. All have great hotels and budget-friendly Airbnbs.

High season in Jamaica ends in April, and Hurricane season doesn’t really get started until July, so April and May can be great months to visit.

Taking a trip to Jamaica?

Cheap flights to St. Maarten: from $112 each way

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Great deals on cheap flights to St. Maarten:

In the Caribbean, Saint Maarten stands out for its unique blend of Dutch and French influences, breathtaking scenery, and vibrant culture. The island blends two European cultures in a one tropical paradise. The Dutch side is known as Sint Maarten, and the French side is called Saint-Martin. The Dutch side is known for its bustling casinos, duty-free shopping, affordable hotels,  activities like sunset tours and kayaking, and vibrant nightlife in places like the capital Philipsburg. The French side offers a more laid-back, European ambiance with charming villages, boutique shops, and a strong culinary scene. Fortunately, it’s easy to move between the two.

Visitors can work on their tans at Maho Beach. It’s famous for its proximity to Princess Juliana International Airport, and airplanes swoop down directly over the beach before landing. Orient Beach, on the French side, is another beloved spot, known for its lively atmosphere and water sports.

Adventure-seekers can explore Saint Maarten’s natural beauty through hiking trails, zip-lining, and snorkeling excursions. The Loterie Farm Nature Reserve on the French side provides a lush escape into the island’s interior, offering hiking trails, a treetop zip line course, and a serene pool area. And the Flying Dutchman, on the Dutch side, is the steepest zip line in the world, offering great views of nearby islands like St. Barth.

St. Maarten also has excellent scuba diving and snorkeling, and is especially known for wreck diving. It’s also the hub for many of the best ferry route in the Caribbean. So if you know you want cheap flights to the Caribbean, but don’t know which island you want to visit, pick St. Maarten. Ferry service will take you to St. Barts, Anguilla, or even Saba.

Taking a trip to St. Maarten?

Cheap flights to Barbados: from $125 each way

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Great deals on cheap flights to Barbados:

Barbados is sometimes called the “Little England” of the Caribbean due to its long history as a British colony. This colonial influence is still evident in large aspects of the culture (its parliamentary system) and smaller aspects, too (its love for cricket). Barbados also has a distinct accent and a strong sense of national identity, making it different from other Caribbean nations that may feel more alike.

One notable feature is Barbados’ geography. Unlike many other Caribbean islands, Barbados is relatively flat and lacks the volcanic or mountainous terrain found elsewhere. This results in a unique landscape characterized by rolling hills, limestone caves, and beautiful coral beaches with calm, clear waters. Barbados is famous for its vibrant festivals and celebrations, such as Crop Over, which showcases the island’s rich cultural heritage and love for music, dance, and colorful costumes. Its bustling capital, Bridgetown, is a UNESCO World Heritage site and offers a blend of historical sites like the Parliament Buildings and modern amenities. So if you’re more into lounging, cultural activities, or culinary travel, booking a cheap flight to the Caribbean island of Barbados may be a good idea.

Oh, and Barbados is known for one other thing: rum. Between distilleries, tasting rooms, and walking and factory tours, you’ll have no shortage of places to find the island’s most well-known spirit.

Taking a trip to Barbados?

Cheap flights to the Turks and Caicos: from $175 each way

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Great deals on cheap flights to Turks and Caicos:

Turks and Caicos is considered part of the Caribbean, but it’s not actually in the Caribbean Sea. It’s in the Atlantic Ocean, to the east of the Bahamas, so it has a more arid climate compared to the lush and humid tropical landscapes of many other Caribbean destinations.

Turks and Caicos is home to the third-largest coral reef system in the world, so look for cheap flights to this Caribbean island if you’re an avid snorkeler or diver. Most hotels are on the islands of Providenciales, North Caicos, and Grand Turk, so the other islands are mostly undeveloped. On them, you’ll find extensive cave systems, lush landscapes, and historical sites like the plantation ruins at Wade’s Green.

Food aficionados shouldn’t miss traditional dishes using conch, readily available on the island. You’ll find lots of various preparations, though cracked conch is probably the most popular. In terms of hotels, you’ll find everything: luxury resorts that feel like you’re on St. Barths (with the prices to match) or more budget-friendly dive hotels with open-air bungalows and easy access to reefs.

Low season is June to November, mostly because that’s when hurricane season is. Since the islands are solidly in the Hurricane Belt, you may not want to plan for those months (or may at least want to wait and book last-minute based on how the weather is looking).

Taking a trip to Turks and Caicos?

Cheap flights to Dominica: from $199 each way

dominica waterfall in the caribbean

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Great deals on cheap flights to Dominica:

Don’t confuse Dominica with the Dominican Republic — they’re two totally different countries. Dominica is often referred to as the “Nature Island of the Caribbean,” with much of the country undeveloped. Unlike in the DR, you won’t find many all-inclusive, budget-friendly resorts for a quick long weekend. But what you will find if you book a cheap flight to the Caribbean destination is an abundance of eco-adventures.

With more than 300 miles of hiking trails, it’s a haven for outdoor enthusiasts. A must-visit attraction is the Morne Trois Pitons National Park, a UNESCO World Heritage site home to Boiling Lake, Titou Gorge, and Trafalgar Falls. The island’s volcanic activity also created lots of natural hot springs, like the ones found at Wotten Waven and Soufrière, where the warm and mineral-rich waters are an ideal place to relax surrounded by jungle.

Dominica’s natural beauty continues below the surface, making it a very popular snorkeling destination. Good sites you won’t want to miss include Champagne Reef, named for the bubbles that rise from the geothermal vents on the seafloor; the Salisbury Marine Reserve, known for clear water and very healthy reefs; and Scott’s Head Pinnacle, so named for the unique underwater shape of the reef.

Taking a trip to Dominica?

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