$133+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — BOS
Jun 21 — Jun 281
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 May 22, 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 May 22, 2026.
This Southwest deal was found by Cheapflights users on 5/21. 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.
Wed 7/810:40 am
SJC
- BOS
2 stops9h 50m
Southwest
Wed 7/155:25 am
BOS
- SJC
1 stop9h 55m
Southwest
Deal found 5/21![Southwest logo]()
$300
This United Airlines deal was found by Cheapflights users on 5/18. 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.
Thu 8/136:37 pm
SJC
- BOS
2 stops10h 40m
United Airlines
Fri 8/216:00 am
BOS
- SJC
1 stop8h 46m
United Airlines
Deal found 5/18![United Airlines logo]()
$301
This Alaska Airlines deal was found by Cheapflights users on 5/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:02 pm
SJC
- BOS
1 stop9h 38m
Alaska Airlines
Wed 8/124:33 pm
BOS
- SJC
1 stop10h 22m
Alaska Airlines
Deal found 5/19![Alaska Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 5/17. 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 9/251:25 pm
SJC
- BOS
1 stop8h 05m
Southwest
Tue 9/295:25 am
BOS
- SJC
2 stops10h 20m
Southwest
Deal found 5/17![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 5/19. 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 9/811:00 pm
SJC
- BOS
1 stop7h 55m
Southwest
Tue 9/157:30 am
BOS
- SJC
2 stops16h 20m
Southwest
Deal found 5/19![Southwest logo]()
$311
This United Airlines deal was found by Cheapflights users on 5/19. 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.
Fri 9/256:37 pm
SJC
- BOS
2 stops11h 09m
United Airlines
Tue 10/66:00 am
BOS
- SJC
1 stop9h 01m
United Airlines
Deal found 5/19![United Airlines logo]()
$313
This United Airlines deal was found by Cheapflights users on 5/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:30 am
SJC
- BOS
2 stops12h 23m
United Airlines
Fri 5/295:05 pm
BOS
- SJC
1 stop8h 30m
United Airlines
Deal found 5/17![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 5/19. 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 7/1012:30 pm
SJC
- BOS
1 stop7h 35m
Southwest
Tue 7/144:25 pm
BOS
- SJC
1 stop9h 00m
Southwest
Deal found 5/19![Southwest logo]()
$317
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Sat 8/156:00 am
SJC
- BOS
1 stop10h 42m
American Airlines
Sat 8/226:00 am
BOS
- SJC
1 stop10h 33m
American Airlines
Deal found 5/21![American Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 5/17. 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 8/216:55 pm
SJC
- BOS
1 stop8h 05m
Southwest
Sun 8/235:55 am
BOS
- SJC
1 stop10h 20m
Southwest
Deal found 5/17![Southwest logo]()
$320
This CheapOair deal was found by Cheapflights users on 5/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:09 am
SJC
- BOS
1 stop17h 31m
Alaska Airlines
Tue 7/147:44 pm
BOS
- SJC
1 stop16h 39m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 5/18. 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 8/1010:10 pm
SJC
- ACK
2 stops13h 31m
Delta
Fri 8/2812:25 pm
ACK
- SJC
2 stops13h 33m
Delta
Deal found 5/18![Delta logo]()
$389
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 May 22, 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 May 22, 2026.
This Southwest deal was found by Cheapflights users on 5/21. 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.
Tue 8/258:15 pm
SJC
- BOS
2 stops10h 15m
Southwest
Wed 9/92:30 pm
BOS
- SJC
2 stops10h 10m
Southwest
Deal found 5/21![Southwest logo]()
$330
This Delta deal was found by Cheapflights users on 5/17. 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 6/167:20 am
SJC
- BOS
1 stop9h 16m
Delta
Wed 6/176:20 am
BOS
- SJC
1 stop10h 59m
Delta
Deal found 5/17![Delta logo]()
$332
This Alaska Airlines deal was found by Cheapflights users on 5/21. 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.
Fri 7/35:02 pm
SJC
- BOS
1 stop9h 38m
Alaska Airlines
Tue 7/144:33 pm
BOS
- SJC
1 stop10h 22m
Alaska Airlines
Deal found 5/21![Alaska Airlines logo]()
$439
This United Airlines deal was found by Cheapflights users on 5/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:30 am
SJC
- BDL
1 stop7h 54m
United Airlines
Wed 10/285:04 pm
BDL
- SJC
1 stop8h 32m
United Airlines
Deal found 5/21![United Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 5/17. 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.
Wed 9/2311:33 am
SJC
- BOS
1 stop9h 50m
Delta
Mon 9/286:30 am
BOS
- SJC
1 stop9h 23m
Delta
Deal found 5/17![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 5/20. 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.
Mon 7/2010:55 pm
SJC
- BOS
1 stop10h 20m
Southwest
Thu 8/68:40 am
BOS
- SJC
1 stop10h 35m
Southwest
Deal found 5/20![Southwest logo]()
$369
This Delta deal was found by Cheapflights users on 5/19. 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.
Mon 6/11:40 pm
SJC
- BOS
1 stop7h 18m
Delta
Thu 6/115:55 am
BOS
- SJC
1 stop9h 10m
Delta
Deal found 5/19![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 5/18. 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.
Fri 7/1012:30 pm
SJC
- BOS
1 stop7h 35m
Southwest
Mon 7/134:45 pm
BOS
- SJC
1 stop9h 40m
Southwest
Deal found 5/18![Southwest logo]()
$369
This Delta deal was found by Cheapflights users on 5/20. 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.
Mon 7/66:12 pm
SJC
- BOS
1 stop8h 16m
Delta
Fri 7/106:05 am
BOS
- SJC
1 stop9h 30m
Delta
Deal found 5/20![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 5/17. 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 7/710:55 pm
SJC
- BDL
1 stop9h 05m
Southwest
Tue 8/45:55 pm
BDL
- SJC
1 stop8h 05m
Southwest
Deal found 5/17![Southwest logo]()
$415
This United Airlines deal was found by Cheapflights users on 5/18. 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.
Tue 9/226:30 am
SJC
- BDL
1 stop8h 15m
United Airlines
Wed 9/234:50 pm
BDL
- SJC
1 stop9h 00m
United Airlines
Deal found 5/18![United Airlines logo]()
$525
This Delta deal was found by Cheapflights users on 5/19. 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.
Sat 8/84:49 pm
SJC
- BOS
1 stop9h 41m
Delta
Tue 8/117:12 am
BOS
- SJC
1 stop8h 15m
Delta
Deal found 5/19![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 5/18. 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.
Tue 6/1611:15 am
SJC
- BOS
1 stop8h 50m
Southwest
Sun 6/285:30 am
BOS
- SJC
1 stop13h 00m
Southwest
Deal found 5/18![Southwest logo]()
$449
This Delta deal was found by Cheapflights users on 5/18. 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.
Wed 7/221:10 pm
SJC
- BDL
1 stop7h 29m
Delta
Wed 7/297:35 am
BDL
- SJC
1 stop7h 26m
Delta
Deal found 5/18![Delta logo]()
$415
This Southwest deal was found by Cheapflights users on 5/19. 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 8/79:15 am
SJC
- BDL
2 stops9h 55m
Southwest
Mon 8/106:20 pm
BDL
- SJC
1 stop8h 00m
Southwest
Deal found 5/19![Southwest logo]()
$455
This Delta deal was found by Cheapflights users on 5/17. 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.
Wed 9/307:15 am
SJC
- BDL
1 stop7h 53m
Delta
Tue 10/135:05 pm
BDL
- SJC
1 stop8h 53m
Delta
Deal found 5/17![Delta logo]()
$415
This Southwest deal was found by Cheapflights users on 5/17. 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 6/2410:40 am
SJC
- BOS
2 stops9h 50m
Southwest
Sat 6/2712:10 pm
BOS
- SJC
1 stop13h 05m
Southwest
Deal found 5/17![Southwest logo]()
$455
This Delta deal was found by Cheapflights users on 5/18. 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 8/115:07 pm
SJC
- ACK
2 stops18h 34m
Delta
Wed 8/263:24 pm
ACK
- SJC
2 stops11h 15m
Delta
Deal found 5/18![Delta logo]()
$436
This Southwest deal was found by Cheapflights users on 5/18. 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.
Wed 6/107:50 pm
SJC
- BDL
2 stops9h 15m
Southwest
Tue 6/164:00 pm
BDL
- SJC
2 stops10h 25m
Southwest
Deal found 5/18![Southwest logo]()
$470
This Delta deal was found by Cheapflights users on 5/18. 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 8/1610:10 pm
SJC
- ACK
2 stops13h 31m
Delta
Fri 8/2812:25 pm
ACK
- SJC
2 stops13h 33m
Delta
Deal found 5/18![Delta logo]()
$451
This United Airlines deal was found by Cheapflights users on 5/18. 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.
Fri 8/146:37 pm
SJC
- ACK
2 stops11h 35m
United Airlines
Sat 8/294:35 pm
ACK
- SJC
1 stop9h 15m
United Airlines
Deal found 5/18![United Airlines logo]()
$850
This Delta deal was found by Cheapflights users on 5/19. 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 6/54:12 pm
SJC
- BOS
1 stop10h 24m
Delta
Sun 6/75:55 am
BOS
- SJC
1 stop9h 10m
Delta
Deal found 5/19![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 5/19. 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.
Tue 6/96:35 am
SJC
- ALB
1 stop7h 59m
Delta
Tue 6/166:00 am
ALB
- SJC
1 stop8h 36m
Delta
Deal found 5/19![Delta logo]()
$456
This Southwest deal was found by Cheapflights users on 5/18. 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.
Wed 6/247:35 pm
SJC
- ALB
2 stops9h 50m
Southwest
Mon 6/299:55 am
ALB
- SJC
2 stops10h 55m
Southwest
Deal found 5/18![Southwest logo]()
$557
This United Airlines deal was found by Cheapflights users on 5/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/152:10 pm
SJC
- ACK
2 stops16h 02m
United Airlines
Wed 8/193:59 pm
ACK
- SJC
2 stops24h 09m
United Airlines
Deal found 5/17![United Airlines logo]()
$936
This Southwest deal was found by Cheapflights users on 5/18. 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 6/114:20 pm
SJC
- ALB
2 stops15h 25m
Southwest
Mon 6/156:05 am
ALB
- SJC
1 stop12h 20m
Southwest
Deal found 5/18![Southwest logo]()
$574
This Delta deal was found by Cheapflights users on 5/18. 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 8/1610:10 pm
SJC
- ACK
2 stops13h 31m
Delta
Thu 8/274:40 pm
ACK
- SJC
2 stops22h 29m
Delta
Deal found 5/18![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 5/17. 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 6/612:12 pm
SJC
- ALB
1 stop8h 46m
Delta
Sat 6/202:38 pm
ALB
- SJC
1 stop10h 04m
Delta
Deal found 5/17![Delta logo]()
$517
This United Airlines deal was found by Cheapflights users on 5/19. 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.
Tue 8/252:10 pm
SJC
- ACK
2 stops16h 02m
United Airlines
Wed 8/263:59 pm
ACK
- SJC
2 stops22h 47m
United Airlines
Deal found 5/19![United Airlines logo]()
$1,118
This Delta deal was found by Cheapflights users on 5/17. 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 7/286:12 pm
SJC
- ALB
2 stops11h 44m
Delta
Sun 8/26:00 am
ALB
- SJC
1 stop8h 30m
Delta
Deal found 5/17![Delta logo]()
$552
Last-minute flights from San Jose to MassachusettsDiscover last-minute flight deals from San Jose to Massachusetts. Data last updated May 22, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Massachusetts. Data last updated May 22, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 5/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:59 am
SJC
- BOS
1 stop11h 00m
Alaska Airlines
Thu 5/284:48 pm
BOS
- SJC
1 stop9h 43m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$305
This United Airlines deal was found by Cheapflights users on 5/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:30 am
SJC
- BOS
2 stops12h 23m
United Airlines
Fri 5/295:05 pm
BOS
- SJC
1 stop8h 30m
United Airlines
Deal found 5/17![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 5/17. 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 5/2711:25 am
SJC
- BOS
2 stops9h 40m
Southwest
Fri 5/293:50 pm
BOS
- SJC
2 stops10h 40m
Southwest
Deal found 5/17![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 5/18. 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.
Fri 5/299:45 pm
SJC
- BOS
1 stop7h 20m
Southwest
Mon 6/13:45 pm
BOS
- SJC
1 stop10h 15m
Southwest
Deal found 5/18![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 5/17. 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 6/57:40 pm
SJC
- BOS
2 stops9h 25m
Southwest
Tue 6/94:25 pm
BOS
- SJC
1 stop9h 00m
Southwest
Deal found 5/17![Southwest logo]()
$364
This CheapOair deal was found by Cheapflights users on 5/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:59 pm
SJC
- BOS
1 stop13h 45m
Alaska Airlines
Wed 6/108:28 am
BOS
- SJC
1 stop12h 32m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 5/18. 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.
Tue 6/99:55 am
SJC
- BOS
1 stop10h 10m
Southwest
Wed 6/103:45 pm
BOS
- SJC
2 stops10h 15m
Southwest
Deal found 5/18![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 5/18. 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 6/95:01 pm
SJC
- ALB
2 stops12h 53m
Delta
Tue 6/166:00 am
ALB
- SJC
1 stop8h 36m
Delta
Deal found 5/18![Delta logo]()
$400
This Delta deal was found by Cheapflights users on 5/17. 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 6/167:20 am
SJC
- BOS
1 stop9h 16m
Delta
Tue 6/236:20 am
BOS
- SJC
1 stop10h 59m
Delta
Deal found 5/17![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 5/18. 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.
Tue 6/1611:15 am
SJC
- BOS
1 stop8h 50m
Southwest
Tue 6/235:35 am
BOS
- SJC
2 stops10h 55m
Southwest
Deal found 5/18![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 5/17. 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 6/1611:15 am
SJC
- BOS
1 stop8h 50m
Southwest
Wed 6/175:35 am
BOS
- SJC
2 stops10h 55m
Southwest
Deal found 5/17![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 5/17. 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 6/3010:40 am
SJC
- BOS
2 stops9h 50m
Southwest
Tue 7/144:25 pm
BOS
- SJC
1 stop9h 00m
Southwest
Deal found 5/17![Southwest logo]()
$365
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 May 22, 2026.
Search for one-way flight options from San Jose to Massachusetts. Find affordable one-way fares based on user searches. Data last updated May 22, 2026.
This Delta deal was found by Cheapflights users on 5/17. 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.
Fri 5/294:59 pm
SJC
- BOS
1 stop10h 21m
Delta
Deal found 5/17![Delta logo]()
$133
This United Airlines deal was found by Cheapflights users on 5/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:37 pm
SJC
- BOS
2 stops12h 14m
United Airlines
Deal found 5/20![United Airlines logo]()
$138
This CheapOair deal was found by Cheapflights users on 5/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:13 am
SJC
- BOS
1 stop19h 27m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$143
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Fri 7/37:22 pm
SJC
- BOS
2 stops10h 58m
American Airlines
Deal found 5/21![American Airlines logo]()
$145
This American Airlines deal was found by Cheapflights users on 5/18. 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.
Wed 9/26:00 am
SJC
- BOS
2 stops10h 42m
American Airlines
Deal found 5/18![American Airlines logo]()
$147
This Delta deal was found by Cheapflights users on 5/18. 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 6/81:10 pm
SJC
- BOS
1 stop7h 47m
Delta
Deal found 5/18![Delta logo]()
$148
This CheapOair deal was found by Cheapflights users on 5/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:59 am
SJC
- BOS
1 stop11h 00m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$153
This American Airlines deal was found by Cheapflights users on 5/19. 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 6/94:26 pm
SJC
- BOS
1 stop10h 32m
American Airlines
Deal found 5/19![American Airlines logo]()
$154
This American Airlines deal was found by Cheapflights users on 5/19. 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.
Sat 7/46:00 am
SJC
- BOS
2 stops11h 59m
American Airlines
Deal found 5/19![American Airlines logo]()
$158
This Delta deal was found by Cheapflights users on 5/20. 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 6/1011:29 am
SJC
- BOS
1 stop9h 52m
Delta
Deal found 5/20![Delta logo]()
$160
This United Airlines deal was found by Cheapflights users on 5/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/86:37 pm
SJC
- BOS
1 stop8h 21m
United Airlines
Deal found 5/17![United Airlines logo]()
$164
This United Airlines deal was found by Cheapflights users on 5/18. 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.
Tue 8/116:20 am
SJC
- BOS
2 stops12h 39m
United Airlines
Deal found 5/18![United Airlines logo]()
$165
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 May 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $300 (Southwest) |
One-way from | $133 (Delta) |
Popular in | April |
Cheapest in | October |
Average price | $378 |
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 May 22, 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
Tue 8/25
8:15 pm-9:30 am
2 stops10h 15m
Boston Logan Intl
Wed 9/9
2:30 pm-9:40 pm
2 stops10h 10m
$330
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Tue 6/16
7:20 am-7:36 pm
1 stop9h 16m
Boston Logan Intl
Wed 6/17
6:20 am-2:19 pm
1 stop10h 59m
$332
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Wed 9/23
11:33 am-12:23 am
1 stop9h 50m
Boston Logan Intl
Mon 9/28
6:30 am-12:53 pm
1 stop9h 23m
$332
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Mon 6/1
1:40 pm-11:58 pm
1 stop7h 18m
Boston Logan Intl
Thu 6/11
5:55 am-12:05 pm
1 stop9h 10m
$359
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Mon 7/20
10:55 pm-12:15 pm
1 stop10h 20m
Boston Logan Intl
Thu 8/6
8:40 am-4:15 pm
1 stop10h 35m
$369
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Fri 7/10
12:30 pm-11:05 pm
1 stop7h 35m
Boston Logan Intl
Mon 7/13
4:45 pm-11:25 pm
1 stop9h 40m
$369
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Mon 7/6
6:12 pm-5:28 am
1 stop8h 16m
Boston Logan Intl
Fri 7/10
6:05 am-12:35 pm
1 stop9h 30m
$399
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Sat 8/8
4:49 pm-5:30 am
1 stop9h 41m
Boston Logan Intl
Tue 8/11
7:12 am-12:27 pm
1 stop8h 15m
$399
San JoseHartford
SJC - BDL
SJCBDL
San Jose
Tue 7/7
10:55 pm-11:00 am
1 stop9h 05m
Hartford Bradley Intl
Tue 8/4
5:55 pm-11:00 pm
1 stop8h 05m
$415
Quickest round-trip
San JoseHartford
SJC - BDL
SJCBDL
San Jose
Wed 7/22
1:10 pm-11:39 pm
1 stop7h 29m
Hartford Bradley Intl
Wed 7/29
7:35 am-12:01 pm
1 stop7h 26m
$415
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-ACK
SJC-ALB
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-ACK
SJC-ALB
What is the cheapest month to book a flight from San Jose, California to Massachusetts?
Currently, June is the cheapest month in which you can book a flight from San Jose, California to Massachusetts (average of $118). Flying from San Jose, California to Massachusetts in March is currently the most expensive (average of $277). 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 38 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 May 22, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, 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.
Entertainment
7.0
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
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 May 22, 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 May 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$350 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$161 | Average$344 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$250 | Average$395 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$252 | Average$372 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$276 | Average$469 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$294 | Average$391 | FlexibilityNo cancel fee | On-time63% |