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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.

£471 London to San Francisco + 14 more deals
🇬🇧From London

£471 London to San Francisco + 14 more deals

This week: direct flights to San Francisco from £471, Barcelona from £65, Singapore from £659, and Business Class deals unlocked for Premium members. Up to 56% below typical prices.

Oct 10
77% off San Francisco → Las Vegas ($38)$38
🇺🇸From San Francisco

77% off San Francisco → Las Vegas ($38)

OAK → Las Vegas for just $38 round-trip - 77% below the typical $164 median - plus SFO → Cancun for $335 (75% off) and SFO → Tokyo for $708.

Oct 9
77% off Los Angeles → Seattle ($38)$38
🇺🇸From Los Angeles

77% off Los Angeles → Seattle ($38)

LAX to Seattle for just $38 round-trip - 77% below the typical $165 median - plus Tokyo Narita for $663 (64% off) and Los Cabos for $340 (50% off) direct from LAX.

Oct 9
88% off US Cities → Seattle ($47)$47

88% off US Cities → Seattle ($47)

LAS → SEA at just $47 round-trip is 88% below typical - plus SEA → Tokyo for $845 (60% off) and ATL → San Juan for $128 (61% off).

Oct 9
39% off New York → Frankfurt ($590)$590
🇺🇸From New York

39% off New York → Frankfurt ($590)

JFK to Frankfurt for just $590 round-trip - 39% below the typical $973 fare - plus direct flights to Aruba from $335 and Cancun from $409 out of Newark.

Oct 9
69% off Washington DC → San Juan ($317)$317
🇺🇸From Washington DC

69% off Washington DC → San Juan ($317)

DCA to San Juan at $317 round-trip is 69% below the typical median - plus Miami for $177 and Seoul for $994 are two more jaw-dropping deals from DC airports this week.

Oct 9

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→

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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