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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.

27 flight deals from London (from £558)
🇬🇧From London

27 flight deals from London (from £558)

LA from £558 return, NYC from £627 - plus Business Class deals and long-haul highlights for Premium members. Prices updated 8 May 2026.

May 9
San Francisco to Seattle for $89?$89
🇺🇸From San Francisco

San Francisco to Seattle for $89?

SFO → Seattle is 55% below its typical median price this week - plus Los Cabos for $179 and Dublin for $664 round-trip.

May 8
72% off Los Angeles → Doha ($843)$843
🇺🇸From Los Angeles

72% off Los Angeles → Doha ($843)

Snag a direct LAX → Doha flight for just $843 round-trip - 72% below the typical median price of $2,964 - plus direct flights to Melbourne for $555 and Auckland for $562.

May 8
Cheapest US Cities → Barcelona we've seen in months: $360$360

Cheapest US Cities → Barcelona we've seen in months: $360

DFW to Barcelona is 93% below typical median pricing - plus Seattle to Paris for $594 and Miami to San Juan for just $91 round-trip.

May 8
67% off Washington DC → Rome ($595)$595
🇺🇸From Washington DC

67% off Washington DC → Rome ($595)

Rome for $595 round-trip from Dulles - 67% below typical - plus Barcelona at $804 and Chicago for just $99 from Reagan National.

May 8
Boston to Punta Cana for $188?$188
🇺🇸From Boston

Boston to Punta Cana for $188?

Punta Cana round-trip at $188 is 62% below typical - plus Cancun for $182 and LA for $119 are turning heads this week from Logan.

May 8

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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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