
Cheap flights from Massachusetts starting at
Popular airlines from Massachusetts
American Airlines
United
JetBlue Airways
Delta
Alaska Airlines
Air Canada
Southwest Airlines
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 30% on select hotels after you book a flight*
Cheapest flights from Massachusetts
These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,088 Return, found 2 days ago
RM1,088
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,129 Return, found 2 days ago
RM1,129
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,185 Return, found 2 days ago
RM1,185
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,195 Return, found 2 days ago
RM1,195
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,226 Return, found 2 days ago
RM1,226
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,236 Return, found 2 days ago
RM1,236
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,252 Return, found 2 days ago
RM1,252
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,273 Return, found 2 days ago
RM1,273
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,283 Return, found 2 days ago
RM1,283
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,293 Return, found 2 days ago
RM1,293
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,300 Return, found 2 days ago
RM1,300
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,312 Return, found 2 days ago
RM1,312
Return
found 2 days ago

Sat, 4 Jul - Sun, 12 Jul
BOS
Boston
LAX
Los Angeles
RM1,313 Return, found 5 days ago
RM1,313
Return
found 5 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,314 Return, found 2 days ago
RM1,314
Return
found 2 days ago

Sat, 4 Jul - Sun, 12 Jul
BOS
Boston
LAX
Los Angeles
RM1,315 Return, found 5 days ago
RM1,315
Return
found 5 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,316 Return, found 2 days ago
RM1,316
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,334 Return, found 2 days ago
RM1,334
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,353 Return, found 2 days ago
RM1,353
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,355 Return, found 2 days ago
RM1,355
Return
found 2 days ago

Thu, 16 Jul - Mon, 20 Jul
BOS
Boston
MCO
Orlando
RM1,454 Return, found 2 days ago
RM1,454
Return
found 2 days ago
Explore a world of travel with Expedia
- 3 Star Hotels in Boston
- 4 Star Hotels in Dunstable
- 5 Star Hotels in Cambridge
- 5 Star Hotels in Lynn
- Apartments in Agawam
- B&B in Amesbury
- B&B in Boston
- Budget Hotels in Boston
- Motel One Hotels in Boston
- Boston Hotels
- Bridgewater Hotels
- Brimfield Hotels
- Cohasset Hotels
- Hilton Hotels in Hanson
- Hotels with Swimming Pools in Haverhill
- Hotels with Swimming Pools in Marlborough
- La Quinta Inn & Suites Hotels in Medway
- Hostels in Taunton
- Budget Hotels in Tewksbury
- Four Seasons Hotels in Wakefield
- Flights to Boston
- Flights to Essex
- Flights to Harvard
- Flights to Leicester
- Flights to Northampton
- Flights to Plymouth
- Flights to Salem
- Flights to Uxbridge
- Flights from Tyngsboro
- Flights from New Bedford
- Flights from Millis
- Flights from Rowe
- Flights from Southborough
- Flights from Swampscott
- Flights from North Attleboro
- Flights from Nantucket
- Flights from Ashfield
- Flights from Athol
- Flights from Cuttyhunk
- Flights from Lunenburg
- Flights from Merrimac
- Flights from Millville
- Flights from Pepperell
- Flights from Royalston
- Flights from Ayer
- Flights from Windsor
- Flights from Ludlow
- Flights from Swansea
- Flights from Ashland
- Flights from Wilbraham
- Flights from Holyoke
- Flights from Mattapoisett
- Flights from North Grafton
- Flights from Shelburne Falls
- Flights from Grafton
- Flights from Somerset
- Flights from Brookline
- Flights from Danvers
- Flights from Billerica
- Flights from Haverhill
- Flights from Lee
- Flights from Methuen
- Flights from Chelsea
- Flights from Westford
- Flights from Randolph
- Flights from Westport
- Flights from Saugus
- Flights from Tewksbury
*Available to Expedia members.