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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 Taipei for $258?$258
🇺🇸From San Francisco

San Francisco to Taipei for $258?

SFO to Taipei at $258 round-trip is 100% below typical - plus London for $283 and Cancun for $344 direct from SFO.

Aug 28
Los Angeles to Seattle for $248?$248
🇺🇸From Los Angeles

Los Angeles to Seattle for $248?

LAX to Seattle for $248 round-trip - 100% below the typical median price - plus Paris for $397 and Los Cabos for just $266 direct from LAX.

Aug 28
US Cities to San Juan for $100?$100

US Cities to San Juan for $100?

Miami to San Juan just hit $100 round-trip - 100% below typical - plus Atlanta to Cancun for $225 direct and Seattle to Amsterdam for $594.

Aug 28
Washington DC to Paris for $672?$672
🇺🇸From Washington DC

Washington DC to Paris for $672?

IAD → Paris for $672 round-trip - 100% below typical - plus San Juan from $137 at BWI and Madrid from $444 at Dulles this week.

Aug 28
Boston to Tokyo Narita for $814?$814
🇺🇸From Boston

Boston to Tokyo Narita for $814?

Round-trip to Tokyo for just $814 - 100% below typical prices from Logan - plus Zurich from $281 direct and Punta Cana from $316 this fall.

Aug 28
UK Regional Airports to Athens for £259?

UK Regional Airports to Athens for £259?

MAN to Athens for just £259 return - a remarkable fare for a direct November flight - plus Alicante from £29 and Toronto from £331 direct with Air Canada.

Aug 28

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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