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Cheap flights to Caribbean from $33 One Way, $61 Round Trip

$61 return flights and $33 one-way flights to Caribbean were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.


Top places to visit in Caribbean

Deals For This Weekend's Flights

Origin Destination Travel Dates Flights From*
EWR San Juan Sep 27 - Sep 29 $81
JFK San Juan Sep 27 - Oct 9 $119
FLL Oranjestad Sep 26 - Oct 3 $197
BOS Nassau Sep 26 - Oct 3 $312
JFK Oranjestad Sep 26 - Oct 19 $381
JFK Oranjestad Sep 26 - Oct 19 $381
EWR Nassau Sep 26 - Oct 1 $382
MIA Oranjestad Sep 26 - Oct 2 $419
JFK Kingston Sep 27 - Oct 5 $461
EWR Licey al Medio Sep 26 - Oct 2 $489
EWR Licey al Medio Sep 26 - Oct 2 $489
EWR Santo Domingo Sep 27 - Oct 3 $514
LGA Punta Cana Sep 26 - Oct 10 $545
EWR Punta Cana Sep 27 - Oct 1 $605
JFK Punta Cana Sep 27 - Oct 1 $631
*Prices include taxes and fees

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Why You Should Take a Flight to the Caribbean

Whether you are after sun, sea, and sand, or rainforests, rum and reggae the glittering islands of the Caribbean offer something for everyone.

Stretching from the Bahamas down to Trinidad and Tobago near Venezuela, the Caribbean is made up of 26 countries, scattered across 7,000 islands.

The region is a cultural melting pot with a rich history and each of the islands has its own identity – you just need to choose one.

When to Book Flights to the Caribbean

With its year-round sunshine there is no bad time to visit the Caribbean, but demand for flights to the islands is at its highest between November and May. This is peak season as people head south from the US and Europe for some winter sun and prices rise accordingly.

The winter months are the driest, although it can get relatively cold in the north.

July to October is hurricane season. It can be hot and sticky at this time of year and it rains, but the chances of being caught up in a major storm are minimal. Some islands, like Aruba and Curacao, lie away from the main hurricane paths.

For the best of both worlds the ideal time for a cheap flight to the Caribbean is in May or September, when there are fewer tourists and the weather is balmy.

How to Find the Best Flight Deals to the Caribbean

With so many island destinations to choose from it should be easy to track down cheap flights to the Caribbean. And there are many ways to find the best deal with Orbitz.

Flexibility on dates and destinations can pay huge dividends. There are flights from all over the US to the nations of the Caribbean and using the ‘Nearby airports’ option beneath your departure and arrival points can help track down a bargain.

The ‘Show flexible dates’ option allows you to compare prices on different days and can open up different routes to your chosen island.

You can filter your results by clicking ‘Show options’ and using the buttons on the left of the results page. You can list flights by price, duration and time of day, compare direct and connecting flights and filter by ticket type or by airline.

Main Airports in the Caribbean

Luis Munoz Marin International Airport (SJU)

The biggest airport in the Caribbean, in terms of passenger numbers, is Luis Munoz Marin International Airport in Puerto Rico. It is a major hub that deals with 9 million people each year. There are flights to and from dozens of US cities and onward services to many of the islands of the Caribbean. Several regional airlines including Air Sunshine are based here.

Punta Cana International Airport (PUJ)

Punta Cana International Airport in the Dominican Republic handles more than 7 million passengers a year. It opened in 1983 as the world’s first privately owned airport. Many flights from North and South America and Europe arrive here.

Jose Marti International Airport (HAV)

The main gateway into Cuba is Jose Marti International Airport, nine miles from the capital Havana. For more than 40 years there were no flights to and from the US, but services resumed in 2016.

Sangster International Airport (MBJ)

Sangster International Airport (MBJ) is the main airport on Jamaica and it handles more than 4 million passengers a year but has the capacity for many more. It lies just a few miles from Montego Bay and there are flights from many US cities.

Which Airlines Fly to the Caribbean?

Major US airlines flying to multiple destinations in the Caribbean include:

  • American Airlines
  • Delta Air Lines
  • JetBlue Airways
  • Southwest Airlines
  • United Airlines

How to Get to and Around the Caribbean

The easiest way to hop from island to island is by plane, and unless you are staying one of the islands with a major international airport you are likely to take a connecting flight to your destination. There are many regional airlines that fly around the region.

Another way to get from one island to another is by boat. There are ferries between some, like the British and US Virgin Islands. You can also live the dream by island-hopping on a chartered yacht.

Once at your destination there are various options for getting around. Hiring a car is one possibility, but be prepared for potholes and stray animals and remember to drive slowly.

Most islands have buses, but they can be crowded and reliability varies. Cycling is also an option depending on where you are (some islands are flatter than others).

Places to Visit in the Caribbean

Harbour Island in the Bahamas has possibly the most breathtaking beach in the Caribbean, with pink sand and azure seas. But there are plenty of rivals around the region. Treasure Beach on Jamaica stretches for six miles and is dotted with archetypal Caribbean beach bars selling cool drinks.

The Caribbean has a long and colorful history. San Juan in Puerto Rico was founded in 1521 and has some spectacular forts and architecture. Just mentioning Havana conjures up romantic images of plazas and brightly colored colonial buildings. Brimstone Hill Fort on St Kitts and Nevis dates to the 17th century and is a UNESCO World Heritage Site.

If you can drag yourself away from the beach its worth exploring the rugged island interiors. Dominica has an aerial tram that runs through rainforest, or you can zipline through the trees in St Lucia.

Tips and Tricks for Traveling in the Caribbean

Talk to the locals, but don’t assume that everyone will speak English. Many places have French, Dutch or Spanish heritage and local dialects can be hard to understand.

People visit the Caribbean to unwind, so slow down and learn to operate on ‘island time’.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.