Flight deals from Boston - Book cheap flights

November 20, 2025

Boston to San Juan, Puerto Rico for only $275 roundtrip

Cheap flights from Boston to San Juan, Puerto Rico for only $275 roundtrip with Delta Air Lines.

November 10, 2025

SUMMER: Boston to the Cayman Islands for only $284 roundtrip

Summer flights from Boston to the Cayman Islands for only $284 roundtrip with United Airlines.

November 7, 2025

Boston to European cities from only $361 roundtrip

Cheap flights from Boston to European cities from only $361 roundtrip with Lufthansa.

November 6, 2025

Non-stop from Boston to Jacksonville, Florida for only $111 roundtrip

Non-stop flights from Boston to Jacksonville, Florida for only $111 roundtrip with JetBlue.

November 4, 2025

Boston to European cities from only $322 roundtrip

Cheap flights from Boston to European cities from only $322 roundtrip with TAP Air Portugal.

November 3, 2025

Boston to Bologna, Italy for only $376 roundtrip

Cheap flights from Boston to Bologna, Italy for only $376 roundtrip with Iberia.

November 1, 2025

Boston to Cluj, Romania for only $389 roundtrip

Cheap flights from Boston to Cluj, Romania for only $389 roundtrip with Lufthansa and Swiss International Air Lines.

October 28, 2025

Non-stop from Boston to Toronto, Canada for only $221 roundtrip

Non-stop flights from Boston to Toronto, Canada for only $221 roundtrip with Air Canada.

October 24, 2025

Boston to Tampa, Florida (& vice versa) for only $118 roundtrip

Cheap flights from Boston to Tampa, Florida for only $118 roundtrip with JetBlue. Also works in reverse.