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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.

🇬🇧From London

San Francisco from £596? Yes, from London

Direct flights to the US West Coast from under £600 return, plus Business Class deals to New York and LA - and 22 premium cabin deals unlocked for subscribers.

Jun 6

$1518

🇺🇸From Boston

Boston to Tel Aviv for $1518?

That BOS-TLV fare is 58% below its typical median price - plus direct flights to Rome from $665 and Nassau from $371 are turning heads this week.

Jun 5

UK Regional Airports to Budapest for £97?

Manchester to Budapest is 74% below typical right now at just £97 return - plus direct flights to Berlin for £50 and Copenhagen for £40 from MAN.

Jun 5

🇬🇧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

$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

$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

Want more deals like these?

Tips for Finding Cheap Flights to The Caribbean

JetBlue and Spirit dominate Caribbean routes with competitive fares
The Dominican Republic and Puerto Rico typically have the cheapest flights
Remember: no passport needed for Puerto Rico or US Virgin Islands
Consider all-inclusive packages — sometimes cheaper than flights + hotel separately
Miami and Fort Lauderdale are the cheapest departure cities for Caribbean flights

Fly to The Caribbean From

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

Other Popular Destinations

🌏Flights to Asia→🌎Flights to South America→🇹🇭Flights to Thailand→🇮🇹Flights to Italy→🇨🇷Flights to Costa Rica→🇪🇸Flights to Spain→

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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