Cheap Flights to the Caribbean: When to Fly, When to Buy

Picture yourself on a beach surrounded by fine white sand and brilliant blue water. In your hand is a drink topped with little umbrellas and in your head is the thought that yes, this is paradise.

Let’s find deals to your favorite Caribbean island.

Caribbean Fun

When to Fly to the Caribbean

  • Cheapest season: Summer is generally a cheaper time to visit the Caribbean. An analysis of FareCompare’s airfare data shows average prices for this summer will peak around the third week in June before gradually lowering, followed by a big price drop in the third week of August. Prices begin to creep up again starting in early October and are most expensive in winter especially around the December holidays.
  • Cheapest days of week: Sundays are often the most expensive days to fly, but not always so compare fares weekends vs. weekdays to be sure of getting the best deal.
  • Best time to fly: Late August through early October.

When to Buy Caribbean Tickets

You can begin shopping about three months before departure and it’s best to have tickets purchased a month before you fly.

Where to Go in the Caribbean

Sorry, we couldn’t list all the Caribbean islands (more here) but these destinations includes popular isles that often have good prices. Learn more about Caribbean attractions, dining and shopping.

  • Click the island’s name to find the cheapest flights.

Antigua:

Antigua
Antigua

You could say Antigua is an island for everyone. Explore the secluded beaches, 18th century dockyards, twin-spire cathedral, pre-historic artifacts, casinos and restaurants – and if you like hot sauce, you’re going to love the local food.

Aruba:

Aruba
Aruba

Do you like windsurfing? Live music and dancing? You’ll like Aruba. Other attractions include the old lighthouse, a butterfly farm and the bird sanctuary and all those pretty beaches. This island is also a popular port-of-call for several cruise lines.

Bahamas:

Bahamas
Bahamas

Did you know the Bahamas is actually made up of about 700 islands spread out over 100,000 miles? But chances are you’re most interested in Nassau and Grand Bahama, with an eclectic mix of “international glamour and tropical ease” as the guide books say. This is where you can ride a horse on the beach, hit the casinos, swim the turquoise waters and tour the romantic city center.

Barbados:

Barbados
Barbados

The easternmost of the Lesser Antilles islands is Barbados sandwiched between the Caribbean Sea and the Atlantic. Looking for luxury? Stay in a world-class hotel or villa on the Platinum Coast. See Bridgetown’s Broad Street and its duty free shopping or go antiquing in buildings and squares dating from the 1600’s, then sit back, relax and enjoy some calypso music.

Bermuda:

Bermuda
Bermuda

Just 650 miles east of North Carolina is the casual and cosmopolitan oasis of Bermuda in what’s considered the northern-most edge of the Caribbean. Tourists cannot rent cars – only mopeds – but it’s the perfect transportation for exploring this charming member of the British Commonwealth. Artists adore Bermuda’s pink beaches, snug white houses and famously friendly people.

Cancun:

Cancun
Cancun

The lovely Mexican town of Cancun is considered part of the Mayan Riviera, home to ancient archaeological sites, amazing craft markets, and a large barrier reef that delights snorkelers with exotic fish and oceanic wonders.

Cuba:

Cuba
Cuba

More and more Americans are expected to learn what others have known for years – that Cuba is a great place to visit. The new FareCompare Cuba Guide has everything you need to know including how to get there.

Dominican Republic:

Dominican Republic
Dominican Republic

Hike a 10,000 foot mountain or explore Santo Domingo, the New World’s oldest city then check out the native wildlife and the incredible coral reefs of the Dominican Republic. Look for many all-inclusive resorts along the gleaming Punta Cana/Bavaro coastline.

Jamaica:

Jamaica
Jamaica

With a magical landscape ranging from tropical rain forest to soaring mountains, Jamaica is always new for visitors. Or maybe they just keep coming back for the beautiful beaches of Montego Bay.

Puerto Rico:

Puerto Rico
Puerto Rico

Enjoy the pretty beaches, stroll past the colonial architecture of Old San Juan, and visit a cathedral dating back to 1540 and do not miss the excellent island cuisine.

Turks and Caicos:

Turks and Caicos
Turks and Caicos

The beaches of Turks and Caicos are white and powdery, the cuisine is international and sophisticated, and the diving is rated ‘superb’. What more could you possibly want? They probably have it.

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Updated: September 16, 2015