Cheap Flights From Philadelphia to Caribbean

Active Caribbean deals departing Philadelphia.

4 active deals

Santo Domingo

Philadelphia → Santo Domingo

$295 USDRoundtrip

✓ $295.33 USDchecked 17 days ago

Jan 19 – Jan 27, 2027 · American Airlines

Found 19 days agoSee deal

Providenciales

Philadelphia → Providenciales

$475 USDRoundtrip

✓ $481.13 USD+$6.13 · checked 18 days ago

Dec 6 – Dec 10, 2026

Found 25 days agoSee deal

Grand Cayman

Philadelphia → Grand Cayman

Multiple sources

$515 USDRoundtrip

✓ $515.01 USDchecked 17 days ago

Dec 7 – Dec 11, 2026

Found 1 month agoSee deal

St. Maarten

Philadelphia → St. Maarten

$343 USDRoundtrip

$509.71 USD+$166.71 · checked 18 days ago

Jan 8 – Jan 11, 2027 · American Airlines · Nonstop

Found 1 month agoSee deal

Other regions from Philadelphia