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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.

San Francisco to Las Vegas for $43?$43
🇺🇸From San Francisco

San Francisco to Las Vegas for $43?

OAK → Las Vegas for just $43 round-trip - 76% below the typical $177 median - plus SJC → LA for $38 and SFO → Dublin for $590 direct with Aer Lingus.

Oct 16
Los Angeles to Los Cabos for $376?$376
🇺🇸From Los Angeles

Los Angeles to Los Cabos for $376?

Alaska Airlines is flying LAX to Los Cabos for $376 round-trip - 58% below the typical median - and that's just the start: Seattle is as low as $102 and Vancouver hits $149 direct with Flair.

Oct 16
US Cities to San Juan for $106?$106

US Cities to San Juan for $106?

ATL → San Juan at $106 round-trip is 80% below its typical median price - plus Tokyo from SEA for $845 and Frankfurt from DEN for $977.

Oct 16
New York to Miami for $239?$239
🇺🇸From New York

New York to Miami for $239?

LGA → Miami is 36% below typical right now at just $239 - plus JFK → San Francisco for $377 and Newark → Lisbon direct for $628.

Oct 16
Washington DC to Madrid for $465?$465
🇺🇸From Washington DC

Washington DC to Madrid for $465?

Dulles to Madrid for $465 round-trip - 85% below typical - plus San Juan from $133 at BWI and Seoul from $994 at IAD.

Oct 16
Boston to Tel Aviv for $967?$967
🇺🇸From Boston

Boston to Tel Aviv for $967?

BOS to Tel Aviv at $967 round-trip is 77% below its typical median price - plus San Juan for $297 and Punta Cana for $370 are turning heads this week.

Oct 16

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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