$108+ Cheap flights from San Jose, CA (SJC) to Massachusetts
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — BOS
Nov 20 — Nov 271
Round-trip
1 adult, Economy
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Find cheap flights from San Jose to Massachusetts with Cheapflights
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Cheapest flights from San Jose to MassachusettsExplore the most affordable flight options available from San Jose to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 21, 2026.
Explore the most affordable flight options available from San Jose to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 21, 2026.
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:25 pm -
2 stops11h 40m
Tue 11/105:00 am -
2 stops10h 15m
Deal found 10/18![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:45 am -
2 stops9h 10m
Mon 11/94:20 pm -
1 stop10h 35m
Deal found 10/19![Southwest logo]()
$299
This SmartFares deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:59 am -
1 stop9h 00m
Wed 12/97:00 am -
1 stop10h 27m
Deal found 10/18![Alaska Airlines logo]()
$302
This Alaska Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Sun 12/67:59 pm -
1 stop18h 09m
Mon 1/46:00 am -
1 stop9h 45m
Deal found 10/21![Alaska Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:50 am -
1 stop9h 55m
Tue 11/175:00 am -
1 stop8h 25m
Deal found 10/18![Southwest logo]()
$307
This Expedia deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/611:38 am -
1 stop26h 30m
Sat 1/26:00 am -
1 stop9h 45m
Deal found 10/21![Alaska Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/166:00 am -
2 stops9h 45m
Fri 1/18:25 am -
1 stop10h 30m
Deal found 10/20![Southwest logo]()
$312
This Alaska Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:39 am -
1 stop10h 19m
Thu 11/127:03 am -
1 stop13h 13m
Deal found 10/20![Alaska Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:35 pm -
2 stops11h 30m
Tue 1/511:20 am -
2 stops10h 10m
Deal found 10/21![Southwest logo]()
$317
This Alaska Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:39 am -
1 stop17h 07m
Tue 11/177:03 am -
1 stop10h 40m
Deal found 10/20![Alaska Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:50 pm -
2 stops8h 25m
Mon 11/94:20 pm -
1 stop10h 35m
Deal found 10/19![Southwest logo]()
$321
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:54 pm -
1 stop10h 26m
Wed 12/27:50 am -
1 stop12h 19m
Deal found 10/16![Delta logo]()
$323
Best flights from San Jose to MassachusettsDiscover carefully curated flight deals from San Jose to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
Discover carefully curated flight deals from San Jose to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:45 am -
2 stops9h 10m
Mon 11/94:20 pm -
1 stop10h 35m
Deal found 10/19![Southwest logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:39 am -
1 stop10h 19m
Thu 11/127:03 am -
1 stop13h 13m
Deal found 10/20![Alaska Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:38 am -
1 stop9h 21m
Wed 12/27:50 am -
1 stop12h 19m
Deal found 10/16![Delta logo]()
$325
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:45 am -
2 stops11h 55m
Sat 11/74:56 pm -
1 stop9h 03m
Deal found 10/16![United Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:14 pm -
2 stops21h 53m
Sat 11/75:36 pm -
2 stops21h 32m
Deal found 10/19![American Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:50 pm -
2 stops8h 25m
Mon 11/94:20 pm -
1 stop10h 35m
Deal found 10/19![Southwest logo]()
$321
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/810:40 pm -
1 stop9h 20m
Fri 11/1311:00 am -
1 stop7h 53m
Deal found 10/16![Delta logo]()
$340
This Southwest deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/131:40 pm -
1 stop7h 15m
Sun 11/155:00 am -
1 stop8h 25m
Deal found 10/17![Southwest logo]()
$340
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:30 am -
1 stop8h 20m
Mon 11/166:45 pm -
1 stop8h 09m
Deal found 10/20![Delta logo]()
$358
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2511:55 am -
1 stop8h 50m
Thu 12/315:00 am -
1 stop8h 25m
Deal found 10/19![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:30 pm -
1 stop8h 38m
Tue 1/57:30 am -
2 stops17h 17m
Deal found 10/21![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/611:33 am -
1 stop9h 29m
Tue 1/53:10 pm -
1 stop10h 02m
Deal found 10/21![Delta logo]()
$382
Last-minute flights from San Jose to MassachusettsDiscover last-minute flight deals from San Jose to Massachusetts. Data last updated October 21, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Massachusetts. Data last updated October 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:45 am -
2 stops9h 10m
Mon 11/94:20 pm -
1 stop10h 35m
Deal found 10/19![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:40 pm -
1 stop7h 19m
Sat 11/710:50 am -
1 stop9h 12m
Deal found 10/16![Delta logo]()
$340
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:50 pm -
2 stops8h 25m
Mon 11/94:20 pm -
1 stop10h 35m
Deal found 10/19![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:25 pm -
2 stops11h 40m
Tue 11/105:00 am -
2 stops10h 15m
Deal found 10/18![Southwest logo]()
$296
This Alaska Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:39 am -
1 stop17h 07m
Tue 11/177:03 am -
1 stop10h 40m
Deal found 10/20![Alaska Airlines logo]()
$318
This Alaska Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:39 am -
1 stop10h 19m
Thu 11/127:03 am -
1 stop13h 13m
Deal found 10/20![Alaska Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:50 am -
1 stop9h 55m
Tue 11/175:00 am -
1 stop8h 25m
Deal found 10/18![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/131:43 pm -
1 stop7h 14m
Mon 11/165:45 am -
1 stop8h 46m
Deal found 10/18![Delta logo]()
$325
This United Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/162:14 pm -
1 stop7h 32m
Mon 11/235:30 am -
2 stops10h 48m
Deal found 10/18![United Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:54 pm -
1 stop10h 26m
Wed 12/27:50 am -
1 stop12h 19m
Deal found 10/16![Delta logo]()
$323
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:00 am -
2 stops9h 45m
Wed 12/26:26 am -
1 stop8h 49m
Deal found 10/21![American Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/3011:00 pm -
1 stop10h 00m
Sat 12/53:10 pm -
1 stop8h 45m
Deal found 10/19![Southwest logo]()
$327
One-way flights from San Jose to MassachusettsSearch for one-way flight options from San Jose to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
Search for one-way flight options from San Jose to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:58 pm -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![American Airlines logo]()
$108
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am -
2 stops10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$113
This Travelocity deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/173:30 pm -
1 stop10h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Alaska Airlines logo]()
$119
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:00 am -
2 stops9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$122
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2411:00 pm -
2 stops12h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![United Airlines logo]()
$124
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2511:38 am -
1 stop9h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Delta logo]()
$129
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/241:40 pm -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$130
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/266:00 am -
1 stop7h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$134
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/271:00 pm -
1 stop9h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$135
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:25 pm -
2 stops8h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Southwest logo]()
$143
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:00 am -
1 stop7h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1711:10 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$155
Find flight deals from San Jose to Massachusetts
Keep the following information in mind while searching for San Jose to Massachusetts flight deals. Data was last updated October 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $296 (Southwest) |
One-way from | $108 (American Airlines) |
Popular in | April |
Cheapest in | August |
Average price | $448 |
Good one-way deal | $289 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 21, 2026.
Use the filters below to find and compare flights from San Jose to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoseBoston
SJC San Jose - BOS Boston Logan Intl
SJCBOS
San Jose
Tue 1/5
8:40 am-7:50 pm
1 stop8h 10m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$108
San JoseBoston
SJC San Jose - BOS Boston Logan Intl
SJCBOS
San Jose
Sat 12/12
1:02 pm-11:45 pm
1 stop7h 43m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$108
San JoseBoston
SJC San Jose - BOS Boston Logan Intl
SJCBOS
San Jose
Tue 2/9
7:50 am-8:50 pm
2 stops10h 00m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$113
San JoseBoston
SJC San Jose - BOS Boston Logan Intl
SJCBOS
San Jose
Thu 12/3
9:00 am-9:55 pm
2 stops9h 55m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$113
San JoseBoston
SJC San Jose - BOS Boston Logan Intl
SJCBOS
San Jose
Wed 11/18
1:26 pm-5:40 am
1 stop13h 14m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$124
San JoseBoston
SJC San Jose - BOS Boston Logan Intl
SJCBOS
San Jose
Mon 1/11
5:45 pm-6:33 am
1 stop9h 48m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$163
San JoseBoston
SJC San Jose - BOS Boston Logan Intl
SJCBOS
San Jose
Mon 12/28
6:12 pm-5:28 am
1 stop8h 16m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$163
Quickest round-trip
San JoseBoston
SJC San Jose - BOS Boston Logan Intl
SJCBOS
San Jose
Tue 1/12
10:30 am-8:50 pm
1 stop7h 20m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$163
San JoseBoston
SJC San Jose - BOS Boston Logan Intl
SJCBOS
San Jose
Wed 11/18
6:30 am-6:57 pm
2 stops9h 27m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$168
San JoseBoston
SJC San Jose - BOS Boston Logan Intl
SJCBOS
San Jose
Mon 11/2
5:10 pm-6:25 am
1 stop10h 15m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$178
Showing 1-10 of 30 resultsSorted by cheapest first
Best time to book a flight from San Jose to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from San Jose with our price prediction graph.
SJC-BOS
SJC-ORH
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Jose to Massachusetts
SJC-USMA
SJC-BOS
SJC-ORH
What is the cheapest month to book a flight from San Jose, California to Massachusetts?
Currently, August is the cheapest month in which you can book a flight from San Jose, California to Massachusetts (average of $338). Flying from San Jose, California to Massachusetts in April is currently the most expensive (average of $522). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from San Jose, California to Massachusetts?
Airfare is below average for this route at the moment.
San Jose, California to Massachusetts flights typically cost between $319 and $574 in November.The cheapest round-trip price found within the last 5 days was $296 on Southwest (Nov 7-Nov 10).
How far ahead should I book a flight from San Jose, California to Massachusetts?
The price you pay for your flight from San Jose, California to Massachusetts may vary depending on when you book. For the best chance of a lower fare, look to book 46 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated October 21, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from San Jose to Massachusetts by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from San Jose to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for San Jose to Massachusetts
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Complete your trip
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Find flights from San Jose to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Jose and Massachusetts flights
Browse other San Jose and Massachusetts flight options. Last updated on October 21, 2026.
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Top 6 airlines flying from San Jose to Massachusetts
Discover the top 6 airlines that operate flights from San Jose to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$367 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$368 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$462 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$280 | Average$426 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$284 | Average$481 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$304 | Average$384 | FlexibilityNo cancel fee | On-time69% |