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Cheap Flights to The Caribbean

Crystal-clear water and white sand beaches — without the premium price tag

Flight Deals to The Caribbean

The Caribbean islands offer some of the most accessible tropical getaways from the US East Coast, with flight times as short as 2-3 hours from Miami and 4-5 from New York. Competition between airlines keeps fares low, especially during the off-season. From all-inclusive resorts in the Dominican Republic to boutique hotels in St. Lucia, there's a Caribbean deal for every budget.

Best Time to Fly to The Caribbean

Late April through November is off-peak season with the cheapest flights. August and September offer the deepest discounts but carry some hurricane risk.

This Week's Picks

See What You're Missing

Real deals from this week - subscribers get these and more, every Friday.

Los Angeles from £572? Yes, from London
🇬🇧From London

Los Angeles from £572? Yes, from London

This week: direct flights to LA from £572, New York from £623, San Francisco from £588 - plus premium cabin deals for subscribers. Save up to 25% vs typical prices.

May 30
New York to Tel Aviv for $2614?$2614
🇺🇸From New York

New York to Tel Aviv for $2614?

JFK to Tel Aviv is 37% below its typical price this week - plus direct flights to Cancun from Newark under $400 and a Dubai deal flying Emirates nonstop.

May 29
57% off Washington DC → Paris ($1048)$1048
🇺🇸From Washington DC

57% off Washington DC → Paris ($1048)

Paris for $1048 round-trip from Dulles - 57% below the typical median price - plus direct flights to London from $880 and Frankfurt from $1234. Summer Europe deals are here.

May 29
Boston to Reykjavik for $478?$478
🇺🇸From Boston

Boston to Reykjavik for $478?

Icelandair is offering BOS to Reykjavik at 53% below typical prices this week - plus direct flights to Barcelona for $587 and Miami for just $157 round-trip.

May 29
UK Regional Airports to Dublin for £30?

UK Regional Airports to Dublin for £30?

MAN to Dublin for just £30 return - 79% below the typical £140 fare - plus Copenhagen for £36 and Faro for £43, all direct from Manchester.

May 29
68% off Asia-Pacific → London Heathrow ($1271)$1271

68% off Asia-Pacific → London Heathrow ($1271)

Cape Town to London Heathrow for just $1271 round-trip - 68% below the typical median price of $3,923 - plus SIN to Tokyo for $345 and HKG to Tokyo for $193.

May 29

Want more deals like these?

Tips for Finding Cheap Flights to The Caribbean

Fly to The Caribbean From

🇺🇸Miami→🇺🇸New York→🇺🇸Boston→🇺🇸Philadelphia→🇺🇸Washington DC→🇺🇸Atlanta→🇺🇸Chicago→

Frequently Asked Questions

What is the cheapest Caribbean island to fly to?

The Dominican Republic (Punta Cana and Santo Domingo) and Puerto Rico (San Juan) consistently have the cheapest flights from the US, with roundtrip fares often under $200 from East Coast cities.

When is hurricane season in the Caribbean?

Official hurricane season runs June through November, with peak activity August through October. Flights are cheapest during this period, and travel insurance is recommended. Many travelers find September and October offer the best risk-reward balance.

Which US cities have the most Caribbean flights?

Miami and Fort Lauderdale have the most Caribbean routes and cheapest fares. New York (JFK), Charlotte, and Atlanta also have extensive Caribbean service with competitive prices.

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