$153+ Cheap flights from San Jose, CA (SJC) to Massachusetts
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — BOS
Aug 18 — Aug 251
Round-trip
1 adult, Economy
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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 July 19, 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 July 19, 2026.
This Southwest deal was found by Cheapflights users on 7/15. 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 8/311:30 pm
SJC
- BOS
1 stop7h 55m
Southwest
Sat 9/55:50 am
BOS
- SJC
1 stop8h 40m
Southwest
Deal found 7/15![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 7/14. 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 8/181:00 pm
SJC
- BOS
1 stop8h 25m
Southwest
Wed 8/262:45 pm
BOS
- SJC
2 stops9h 55m
Southwest
Deal found 7/14![Southwest logo]()
$280
This American Airlines deal was found by Cheapflights users on 7/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:42 pm
SJC
- BOS
1 stop7h 42m
American Airlines
Sun 9/610:00 am
BOS
- SJC
1 stop8h 29m
American Airlines
Deal found 7/18![American Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 7/15. 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 8/297:30 pm
SJC
- BOS
2 stops10h 10m
Southwest
Sat 9/58:40 am
BOS
- SJC
2 stops12h 35m
Southwest
Deal found 7/15![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 7/18. 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 8/1012:30 pm
SJC
- BOS
1 stop8h 55m
Southwest
Tue 8/187:30 am
BOS
- SJC
2 stops16h 20m
Southwest
Deal found 7/18![Southwest logo]()
$286
This Delta deal was found by Cheapflights users on 7/14. 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 8/1611:38 am
SJC
- BOS
1 stop9h 13m
Delta
Tue 8/256:05 am
BOS
- SJC
1 stop9h 49m
Delta
Deal found 7/14![Delta logo]()
$290
This Delta deal was found by Cheapflights users on 7/15. 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 8/1411:38 am
SJC
- BOS
1 stop9h 13m
Delta
Sat 8/2210:50 am
BOS
- SJC
1 stop9h 37m
Delta
Deal found 7/15![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 7/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:55 am
SJC
- BOS
2 stops10h 10m
Southwest
Sun 8/305:55 am
BOS
- SJC
1 stop10h 20m
Southwest
Deal found 7/16![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 7/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:40 am
SJC
- BOS
2 stops9h 45m
Southwest
Tue 8/257:30 am
BOS
- SJC
2 stops9h 50m
Southwest
Deal found 7/16![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 7/14. 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.
Sun 8/166:05 am
SJC
- BOS
1 stop11h 20m
Southwest
Tue 8/187:30 am
BOS
- SJC
2 stops16h 20m
Southwest
Deal found 7/14![Southwest logo]()
$301
This Delta deal was found by Cheapflights users on 7/14. 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 7/214:30 pm
SJC
- BOS
1 stop10h 00m
Delta
Tue 7/286:05 am
BOS
- SJC
1 stop9h 30m
Delta
Deal found 7/14![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 7/15. 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 8/218:40 pm
SJC
- BOS
2 stops10h 15m
Southwest
Mon 8/245:50 am
BOS
- SJC
1 stop10h 10m
Southwest
Deal found 7/15![Southwest logo]()
$309
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 July 19, 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 July 19, 2026.
This Delta deal was found by Cheapflights users on 7/14. 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 9/1811:36 am
SJC
- BOS
1 stop9h 15m
Delta
Tue 9/223:10 pm
BOS
- SJC
1 stop9h 12m
Delta
Deal found 7/14![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 7/15. 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 9/298:40 am
SJC
- BOS
2 stops9h 40m
Southwest
Wed 10/146:45 am
BOS
- SJC
1 stop10h 40m
Southwest
Deal found 7/15![Southwest logo]()
$280
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Sat 9/196:30 am
SJC
- BDL
1 stop8h 15m
United Airlines
Wed 9/239:15 am
BDL
- SJC
2 stops11h 16m
United Airlines
Deal found 7/18![United Airlines logo]()
$452
This Delta deal was found by Cheapflights users on 7/15. 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 9/165:40 pm
SJC
- BOS
1 stop11h 00m
Delta
Mon 9/215:55 am
BOS
- SJC
1 stop9h 32m
Delta
Deal found 7/15![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 7/19. 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 8/1811:30 am
SJC
- BOS
1 stop9h 55m
Southwest
Tue 8/259:25 am
BOS
- SJC
2 stops10h 00m
Southwest
Deal found 7/19![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 7/18. 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.
Mon 8/107:00 am
SJC
- BOS
1 stop9h 25m
Delta
Wed 8/196:25 am
BOS
- SJC
1 stop10h 49m
Delta
Deal found 7/18![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 7/17. 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.
Tue 10/207:20 am
SJC
- BOS
2 stops10h 55m
Southwest
Thu 10/229:05 am
BOS
- SJC
1 stop8h 20m
Southwest
Deal found 7/17![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 7/18. 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 8/711:38 am
SJC
- BOS
1 stop9h 13m
Delta
Tue 8/185:51 am
BOS
- SJC
1 stop9h 36m
Delta
Deal found 7/18![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 7/14. 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 8/131:30 pm
SJC
- BOS
1 stop7h 55m
Southwest
Thu 8/207:30 am
BOS
- SJC
2 stops10h 50m
Southwest
Deal found 7/14![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 7/18. 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 8/76:12 pm
SJC
- BOS
1 stop8h 18m
Delta
Thu 8/203:14 pm
BOS
- SJC
1 stop10h 44m
Delta
Deal found 7/18![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 7/14. 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 10/16:00 am
SJC
- BOS
2 stops10h 15m
Southwest
Mon 10/55:35 am
BOS
- SJC
1 stop11h 50m
Southwest
Deal found 7/14![Southwest logo]()
$321
This Gotogate deal was found by Cheapflights users on 7/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:46 pm
SJC
- PVC
2 stops12h 47m
Multiple Airlines
Sat 9/56:45 am
PVC
- SJC
2 stops12h 39m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$945
This Southwest deal was found by Cheapflights users on 7/14. 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 10/159:40 pm
SJC
- BOS
1 stop7h 30m
Southwest
Sun 10/185:35 am
BOS
- SJC
1 stop8h 50m
Southwest
Deal found 7/14![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 7/14. 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.
Tue 8/1112:51 pm
SJC
- ALB
1 stop7h 44m
United Airlines
Tue 8/186:00 am
ALB
- SJC
1 stop8h 46m
United Airlines
Deal found 7/14![United Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 7/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/211:47 am
SJC
- HYA
2 stops22h 09m
American Airlines
Thu 8/612:42 pm
HYA
- SJC
2 stops12h 29m
American Airlines
Deal found 7/18![American Airlines logo]()
$1,096
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Wed 8/196:37 pm
SJC
- BDL
2 stops12h 00m
United Airlines
Sun 8/236:00 am
BDL
- SJC
1 stop8h 46m
United Airlines
Deal found 7/18![United Airlines logo]()
$512
This Southwest deal was found by Cheapflights users on 7/17. 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 9/1110:30 pm
SJC
- BDL
1 stop9h 00m
Southwest
Sun 9/135:20 am
BDL
- SJC
1 stop10h 55m
Southwest
Deal found 7/17![Southwest logo]()
$384
This United Airlines deal was found by Cheapflights users on 7/16. 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.
Fri 8/76:37 pm
SJC
- ALB
2 stops12h 34m
United Airlines
Thu 8/136:00 am
ALB
- SJC
1 stop8h 46m
United Airlines
Deal found 7/16![United Airlines logo]()
$540
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/41:24 pm
SJC
- BDL
1 stop7h 01m
Delta
Thu 8/1311:30 am
BDL
- SJC
1 stop10h 22m
Delta
Deal found 7/17![Delta logo]()
$457
This Southwest deal was found by Cheapflights users on 7/15. 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 8/1411:00 pm
SJC
- BDL
1 stop9h 05m
Southwest
Sat 8/2911:45 am
BDL
- SJC
2 stops10h 20m
Southwest
Deal found 7/15![Southwest logo]()
$389
This Delta deal was found by Cheapflights users on 7/18. 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.
Sun 9/137:11 pm
SJC
- ALB
2 stops13h 03m
Delta
Sun 9/206:15 am
ALB
- SJC
1 stop8h 21m
Delta
Deal found 7/18![Delta logo]()
$462
This Southwest deal was found by Cheapflights users on 7/14. 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 9/1111:00 pm
SJC
- ALB
1 stop8h 45m
Southwest
Sun 9/136:10 am
ALB
- SJC
1 stop10h 05m
Southwest
Deal found 7/14![Southwest logo]()
$395
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Sat 8/228:45 am
SJC
- ACK
2 stops28h 04m
United Airlines
Wed 8/269:50 am
ACK
- SJC
2 stops14h 07m
United Airlines
Deal found 7/18![United Airlines logo]()
$611
This Delta deal was found by Cheapflights users on 7/18. 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 8/287:00 am
SJC
- ALB
2 stops13h 05m
Delta
Sun 8/306:00 am
ALB
- SJC
2 stops9h 27m
Delta
Deal found 7/18![Delta logo]()
$468
This Southwest deal was found by Cheapflights users on 7/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1611:00 pm
SJC
- ALB
1 stop9h 15m
Southwest
Wed 10/216:25 pm
ALB
- SJC
1 stop7h 50m
Southwest
Deal found 7/16![Southwest logo]()
$395
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:40 am
SJC
- BDL
1 stop10h 50m
Delta
Tue 8/111:54 pm
BDL
- SJC
1 stop10h 47m
Delta
Deal found 7/17![Delta logo]()
$478
This United Airlines deal was found by Cheapflights users on 7/16. 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.
Mon 8/246:37 pm
SJC
- ACK
3 stops17h 26m
United Airlines
Fri 8/284:15 pm
ACK
- SJC
2 stops22h 30m
United Airlines
Deal found 7/16![United Airlines logo]()
$657
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:12 pm
SJC
- ALB
2 stops14h 33m
Delta
Mon 9/76:00 am
ALB
- SJC
2 stops9h 27m
Delta
Deal found 7/17![Delta logo]()
$489
This Southwest deal was found by Cheapflights users on 7/17. 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.
Wed 8/128:45 am
SJC
- ALB
2 stops9h 15m
Southwest
Mon 8/176:00 am
ALB
- SJC
2 stops9h 40m
Southwest
Deal found 7/17![Southwest logo]()
$459
This Travelocity deal was found by Cheapflights users on 7/19. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:46 pm
SJC
- MVY
2 stops15h 09m
Multiple Airlines
Thu 10/156:44 am
MVY
- SJC
2 stops12h 54m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$1,183
Last-minute flights from San Jose to MassachusettsDiscover last-minute flight deals from San Jose to Massachusetts. Data last updated July 19, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Massachusetts. Data last updated July 19, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/14. 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 7/214:30 pm
SJC
- BOS
1 stop10h 00m
Delta
Wed 7/2210:55 am
BOS
- SJC
1 stop9h 17m
Delta
Deal found 7/14![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 7/18. 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 8/1012:30 pm
SJC
- BOS
1 stop8h 55m
Southwest
Tue 8/187:30 am
BOS
- SJC
2 stops16h 20m
Southwest
Deal found 7/18![Southwest logo]()
$286
This Delta deal was found by Cheapflights users on 7/15. 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 8/1411:38 am
SJC
- BOS
1 stop9h 13m
Delta
Sat 8/2210:50 am
BOS
- SJC
1 stop9h 37m
Delta
Deal found 7/15![Delta logo]()
$292
This Delta deal was found by Cheapflights users on 7/14. 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 8/1611:38 am
SJC
- BOS
1 stop9h 13m
Delta
Tue 8/256:05 am
BOS
- SJC
1 stop9h 49m
Delta
Deal found 7/14![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 7/14. 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.
Sun 8/166:05 am
SJC
- BOS
1 stop11h 20m
Southwest
Tue 8/187:30 am
BOS
- SJC
2 stops16h 20m
Southwest
Deal found 7/14![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 7/14. 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 8/181:00 pm
SJC
- BOS
1 stop8h 25m
Southwest
Wed 8/262:45 pm
BOS
- SJC
2 stops9h 55m
Southwest
Deal found 7/14![Southwest logo]()
$280
This Southwest deal was found by Cheapflights users on 7/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:40 am
SJC
- BOS
2 stops9h 45m
Southwest
Tue 8/257:30 am
BOS
- SJC
2 stops9h 50m
Southwest
Deal found 7/16![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 7/15. 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 8/218:40 pm
SJC
- BOS
2 stops10h 15m
Southwest
Mon 8/245:50 am
BOS
- SJC
1 stop10h 10m
Southwest
Deal found 7/15![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 7/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:55 am
SJC
- BOS
2 stops10h 10m
Southwest
Sun 8/305:55 am
BOS
- SJC
1 stop10h 20m
Southwest
Deal found 7/16![Southwest logo]()
$295
This American Airlines deal was found by Cheapflights users on 7/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:42 pm
SJC
- BOS
1 stop7h 42m
American Airlines
Sun 9/610:00 am
BOS
- SJC
1 stop8h 29m
American Airlines
Deal found 7/18![American Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 7/15. 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 8/297:30 pm
SJC
- BOS
2 stops10h 10m
Southwest
Sat 9/58:40 am
BOS
- SJC
2 stops12h 35m
Southwest
Deal found 7/15![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 7/15. 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 8/311:30 pm
SJC
- BOS
1 stop7h 55m
Southwest
Sat 9/55:50 am
BOS
- SJC
1 stop8h 40m
Southwest
Deal found 7/15![Southwest logo]()
$275
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 July 19, 2026.
Search for one-way flight options from San Jose to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 19, 2026.
This Delta deal was found by Cheapflights users on 7/14. 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 7/2810:00 pm
SJC
- BOS
1 stop8h 39m
Delta
Deal found 7/14![Delta logo]()
$153
This Delta deal was found by Cheapflights users on 7/14. 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 9/221:23 pm
SJC
- BDL
1 stop7h 22m
Delta
Deal found 7/14![Delta logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:03 pm
SJC
- BOS
2 stops34h 06m
Frontier
Deal found 7/16![Frontier logo]()
$157
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:10 pm
SJC
- BOS
1 stop10h 20m
Delta
Deal found 7/17![Delta logo]()
$158
This American Airlines deal was found by Cheapflights users on 7/14. 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 8/46:01 am
SJC
- BDL
2 stops13h 59m
American Airlines
Deal found 7/14![American Airlines logo]()
$161
This CheapOair deal was found by Cheapflights users on 7/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2510:03 am
SJC
- BOS
1 stop16h 37m
Alaska Airlines
Deal found 7/16![Alaska Airlines logo]()
$163
This Southwest deal was found by Cheapflights users on 7/15. 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 7/244:20 pm
SJC
- BOS
2 stops13h 20m
Southwest
Deal found 7/15![Southwest logo]()
$164
This Delta deal was found by Cheapflights users on 7/15. 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 8/512:40 pm
SJC
- ALB
1 stop8h 17m
Delta
Deal found 7/15![Delta logo]()
$167
This Southwest deal was found by Cheapflights users on 7/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:40 am
SJC
- BOS
1 stop9h 45m
Southwest
Deal found 7/16![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 7/17. 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.
Mon 8/108:40 pm
SJC
- BOS
2 stops9h 50m
Southwest
Deal found 7/17![Southwest logo]()
$168
This Delta deal was found by Cheapflights users on 7/18. 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.
Tue 8/111:24 pm
SJC
- BDL
1 stop7h 01m
Delta
Deal found 7/18![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 7/15. 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 8/58:40 am
SJC
- ALB
2 stops9h 20m
Southwest
Deal found 7/15![Southwest logo]()
$172
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 July 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $275 (Southwest) |
One-way from | $153 (Delta) |
Popular in | April |
Cheapest in | October |
Average price | $383 |
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 2,558,603 searches. Data last updated July 19, 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 - BOS
SJCBOS
San Jose
Fri 9/18
11:36 am-11:51 pm
1 stop9h 15m
Boston Logan Intl
Tue 9/22
3:10 pm-9:22 pm
1 stop9h 12m
$275
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Wed 9/16
5:40 pm-7:40 am
1 stop11h 00m
Boston Logan Intl
Mon 9/21
5:55 am-12:27 pm
1 stop9h 32m
$275
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Mon 8/10
7:00 am-7:25 pm
1 stop9h 25m
Boston Logan Intl
Wed 8/19
6:25 am-2:14 pm
1 stop10h 49m
$275
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Tue 9/29
8:40 am-9:20 pm
2 stops9h 40m
Boston Logan Intl
Wed 10/14
6:45 am-2:25 pm
1 stop10h 40m
$280
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Tue 8/18
11:30 am-12:25 am
1 stop9h 55m
Boston Logan Intl
Tue 8/25
9:25 am-4:25 pm
2 stops10h 00m
$280
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Tue 10/20
7:20 am-9:15 pm
2 stops10h 55m
Boston Logan Intl
Thu 10/22
9:05 am-2:25 pm
1 stop8h 20m
$280
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Fri 8/7
11:38 am-11:51 pm
1 stop9h 13m
Boston Logan Intl
Tue 8/18
5:51 am-12:27 pm
1 stop9h 36m
$290
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Fri 8/7
6:12 pm-5:30 am
1 stop8h 18m
Boston Logan Intl
Thu 8/20
3:14 pm-10:58 pm
1 stop10h 44m
$290
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Thu 8/13
1:30 pm-12:25 am
1 stop7h 55m
Boston Logan Intl
Thu 8/20
7:30 am-3:20 pm
2 stops10h 50m
$295
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Thu 10/1
6:00 am-7:15 pm
2 stops10h 15m
Boston Logan Intl
Mon 10/5
5:35 am-2:25 pm
1 stop11h 50m
$321
Showing 1-10 of 60 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-BDL
SJC-ALB
SJC-MVY
SJC-PVC
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-BDL
SJC-ALB
SJC-MVY
What is the cheapest month to book a flight from San Jose, California to Massachusetts?
Currently, October is the cheapest month in which you can book a flight from San Jose, California to Massachusetts (average of $342). 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?
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 35 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 July 19, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta 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.
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
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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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 July 19, 2026.
Popular flight searches
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San Jose to Massachusetts flights
Consider these flights traveling from San Jose to Massachusetts.
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 2,558,603 searches. Data last updated July 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$334 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$161 | Average$345 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$250 | Average$476 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$270 | Average$442 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$273 | Average$482 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$297 | Average$416 | FlexibilityNo cancel fee | On-time63% |