← Boston Deals / Caribbean

Cheap Flights From Boston to Caribbean

Active Caribbean deals departing Boston.

7 active deals

Grand Cayman

Boston → Grand Cayman

$391 USDRoundtrip

✓ $390.65 USDchecked 16 days ago
Dec 3 – Dec 7, 2026
Found 17 days agoSee deal

San Juan

Boston → San Juan

$257 USDRoundtrip

$418.96 USD+$161.96 · checked 18 days ago
Oct 23 – Oct 26, 2026 · Delta Air Lines
Found 1 month agoSee deal

Nassau

Boston → Nassau

$328 USDRoundtrip

$435.43 USD+$107.43 · checked 18 days ago
Dec 4 – Dec 11, 2026
Found 25 days agoSee deal

Providenciales

Boston → Providenciales

$372 USDRoundtrip

$442.73 USD+$70.73 · checked 18 days ago
Dec 9 – Dec 16, 2026
Found 25 days agoSee deal

Punta Cana

Boston → Punta Cana

$339 USDRoundtrip

$481.83 USD+$142.83 · checked 16 days ago
Jan 23 – Jan 26, 2027 · JetBlue · Nonstop
Found 17 days agoSee deal

Aruba

Boston → Aruba

$424 USDRoundtrip

$572.69 USD+$148.69 · checked 18 days ago
Nov 8 – Nov 15, 2026
Found 1 month agoSee deal

St. Maarten

Boston → St. Maarten

$305 USDRoundtrip

$701.52 USD+$396.52 · checked 18 days ago
Oct 27 – Oct 31, 2026 · United Airlines · 1 stop
Found 23 days agoSee deal

Other regions from Boston

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