$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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — BOS
Jul 23 — Jul 301
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 June 23, 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 June 23, 2026.
This American Airlines deal was found by Cheapflights users on 6/22. 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 9/212:49 pm
SJC
- BOS
1 stop7h 35m
American Airlines
Sun 9/66:00 am
BOS
- SJC
1 stop10h 40m
American Airlines
Deal found 6/22![American Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 6/20. 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 6/296:20 am
SJC
- BOS
1 stop7h 25m
Delta
Sat 7/410:55 am
BOS
- SJC
1 stop8h 10m
Delta
Deal found 6/20![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 6/19. 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 7/2811:15 am
SJC
- BOS
1 stop9h 05m
Southwest
Wed 7/298:45 am
BOS
- SJC
1 stop13h 30m
Southwest
Deal found 6/19![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 6/19. 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.
Wed 8/1212:40 pm
SJC
- BOS
1 stop9h 45m
Delta
Mon 8/245:51 am
BOS
- SJC
1 stop9h 36m
Delta
Deal found 6/19![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 6/22. 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.
Thu 7/911:47 am
SJC
- BOS
1 stop9h 12m
American Airlines
Fri 7/177:00 am
BOS
- SJC
1 stop7h 59m
American Airlines
Deal found 6/22![American Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 6/18. 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 9/181:25 pm
SJC
- BOS
1 stop8h 05m
Southwest
Wed 9/237:30 am
BOS
- SJC
2 stops16h 20m
Southwest
Deal found 6/18![Southwest logo]()
$301
This Delta deal was found by Cheapflights users on 6/18. 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 8/315:10 pm
SJC
- BOS
1 stop10h 20m
Delta
Sun 9/65:51 am
BOS
- SJC
1 stop9h 18m
Delta
Deal found 6/18![Delta logo]()
$304
This CheapOair deal was found by Cheapflights users on 6/18. 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 8/1010:03 am
SJC
- BOS
1 stop16h 37m
Alaska Airlines
Wed 8/268:00 am
BOS
- SJC
1 stop8h 30m
Alaska Airlines
Deal found 6/18![Alaska Airlines logo]()
$305
This United Airlines deal was found by Cheapflights users on 6/20. 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.
Thu 8/132:10 pm
SJC
- BOS
1 stop8h 01m
United Airlines
Sat 8/226:01 am
BOS
- SJC
1 stop8h 44m
United Airlines
Deal found 6/20![United Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 6/19. 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 7/2811:15 am
SJC
- BOS
1 stop9h 05m
Southwest
Tue 8/410:50 am
BOS
- SJC
1 stop10h 30m
Southwest
Deal found 6/19![Southwest logo]()
$310
This United Airlines deal was found by Cheapflights users on 6/17. 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 9/236:37 pm
SJC
- BOS
2 stops11h 10m
United Airlines
Fri 9/256:00 am
BOS
- SJC
1 stop9h 01m
United Airlines
Deal found 6/17![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 6/22. 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 9/196:30 am
SJC
- BDL
1 stop10h 48m
Delta
Tue 9/292:04 pm
BDL
- SJC
1 stop10h 18m
Delta
Deal found 6/22![Delta logo]()
$355
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 June 23, 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 June 23, 2026.
This Delta deal was found by Cheapflights users on 6/19. 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.
Wed 8/1212:40 pm
SJC
- BOS
1 stop9h 45m
Delta
Fri 8/214:25 pm
BOS
- SJC
1 stop9h 33m
Delta
Deal found 6/19![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 6/17. 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 9/236:37 pm
SJC
- BOS
2 stops11h 10m
United Airlines
Fri 9/256:00 am
BOS
- SJC
1 stop9h 01m
United Airlines
Deal found 6/17![United Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 6/19. 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 7/158:55 am
SJC
- BOS
2 stops10h 50m
Southwest
Wed 7/223:45 pm
BOS
- SJC
1 stop9h 45m
Southwest
Deal found 6/19![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 6/21. 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.
Mon 8/106:10 am
SJC
- BOS
1 stop10h 05m
Delta
Fri 8/145:51 am
BOS
- SJC
1 stop9h 36m
Delta
Deal found 6/21![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 6/22. 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 7/277:23 pm
SJC
- ACK
2 stops16h 45m
American Airlines
Thu 7/3012:56 pm
ACK
- SJC
2 stops12h 45m
American Airlines
Deal found 6/22![American Airlines logo]()
$695
This Southwest deal was found by Cheapflights users on 6/18. 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 9/2611:00 pm
SJC
- BDL
1 stop9h 20m
Southwest
Tue 10/65:35 am
BDL
- SJC
1 stop8h 45m
Southwest
Deal found 6/18![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 6/19. 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 7/285:01 pm
SJC
- BOS
1 stop10h 04m
Delta
Thu 8/66:25 am
BOS
- SJC
1 stop10h 49m
Delta
Deal found 6/19![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 6/21. 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.
Sun 7/56:37 pm
SJC
- BOS
1 stop8h 21m
United Airlines
Wed 7/88:15 am
BOS
- SJC
2 stops12h 20m
United Airlines
Deal found 6/21![United Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 6/17. 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 11/171:40 pm
SJC
- BOS
1 stop7h 00m
Southwest
Tue 12/12:30 pm
BOS
- SJC
1 stop10h 05m
Southwest
Deal found 6/17![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 6/20. 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.
Tue 9/812:46 pm
SJC
- BDL
1 stop8h 12m
Delta
Wed 9/166:00 am
BDL
- SJC
1 stop8h 36m
Delta
Deal found 6/20![Delta logo]()
$355
This Southwest deal was found by Cheapflights users on 6/22. 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
Fri 7/244:45 pm
BOS
- SJC
1 stop9h 45m
Southwest
Deal found 6/22![Southwest logo]()
$389
This Delta deal was found by Cheapflights users on 6/21. 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 8/206:40 am
SJC
- BDL
1 stop10h 50m
Delta
Sat 8/296:00 am
BDL
- SJC
1 stop8h 28m
Delta
Deal found 6/21![Delta logo]()
$368
This United Airlines deal was found by Cheapflights users on 6/20. 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.
Tue 9/16:20 am
SJC
- BDL
1 stop9h 00m
United Airlines
Wed 9/24:50 pm
BDL
- SJC
1 stop9h 00m
United Airlines
Deal found 6/20![United Airlines logo]()
$465
This Southwest deal was found by Cheapflights users on 6/18. 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 7/244:20 pm
SJC
- BOS
2 stops13h 20m
Southwest
Wed 7/293:45 pm
BOS
- SJC
2 stops10h 20m
Southwest
Deal found 6/18![Southwest logo]()
$406
This Delta deal was found by Cheapflights users on 6/17. 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 8/1010:20 pm
SJC
- BOS
1 stop8h 19m
Delta
Sun 8/166:25 am
BOS
- SJC
1 stop10h 49m
Delta
Deal found 6/17![Delta logo]()
$397
This Southwest deal was found by Cheapflights users on 6/22. 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 7/238:50 am
SJC
- BOS
1 stop12h 25m
Southwest
Sat 7/254:00 pm
BOS
- SJC
1 stop8h 20m
Southwest
Deal found 6/22![Southwest logo]()
$410
This Southwest deal was found by Cheapflights users on 6/21. 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 8/1511:00 pm
SJC
- ALB
1 stop10h 20m
Southwest
Sun 8/235:40 am
ALB
- SJC
1 stop8h 05m
Southwest
Deal found 6/21![Southwest logo]()
$412
This Delta deal was found by Cheapflights users on 6/21. 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 8/276:40 am
SJC
- BDL
1 stop8h 25m
Delta
Sun 8/306:50 am
BDL
- SJC
1 stop8h 37m
Delta
Deal found 6/21![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 6/20. 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 9/246:59 am
SJC
- ALB
2 stops13h 09m
Delta
Sun 9/276:25 am
ALB
- SJC
1 stop8h 11m
Delta
Deal found 6/20![Delta logo]()
$424
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Thu 7/2312:39 pm
SJC
- ACK
2 stops19h 10m
American Airlines
Sat 7/2510:23 am
ACK
- SJC
2 stops15h 18m
American Airlines
Deal found 6/21![American Airlines logo]()
$825
This Delta deal was found by Cheapflights users on 6/19. 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 8/2112:35 pm
SJC
- BDL
1 stop8h 23m
Delta
Tue 8/256:00 am
BDL
- SJC
1 stop8h 22m
Delta
Deal found 6/19![Delta logo]()
$440
This United Airlines deal was found by Cheapflights users on 6/21. 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 8/298:45 am
SJC
- ACK
2 stops27h 53m
United Airlines
Tue 9/14:15 pm
ACK
- SJC
2 stops28h 16m
United Airlines
Deal found 6/21![United Airlines logo]()
$779
This Delta deal was found by Cheapflights users on 6/18. 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 9/1310:20 pm
SJC
- ALB
1 stop9h 56m
Delta
Sun 9/206:25 am
ALB
- SJC
1 stop8h 11m
Delta
Deal found 6/18![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 6/18. 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 8/164:30 pm
SJC
- ACK
2 stops19h 11m
Delta
Fri 8/2812:28 pm
ACK
- SJC
2 stops13h 30m
Delta
Deal found 6/18![Delta logo]()
$582
This Delta deal was found by Cheapflights users on 6/18. 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 7/2010:00 pm
SJC
- ACK
2 stops13h 41m
Delta
Wed 7/294:40 pm
ACK
- SJC
2 stops21h 50m
Delta
Deal found 6/18![Delta logo]()
$622
This Delta deal was found by Cheapflights users on 6/18. 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 7/2110:00 pm
SJC
- ACK
2 stops14h 48m
Delta
Fri 7/243:24 pm
ACK
- SJC
2 stops22h 14m
Delta
Deal found 6/18![Delta logo]()
$656
This Delta deal was found by Cheapflights users on 6/18. 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 8/1412:35 pm
SJC
- ACK
2 stops24h 22m
Delta
Fri 8/283:24 pm
ACK
- SJC
2 stops11h 20m
Delta
Deal found 6/18![Delta logo]()
$667
This Delta deal was found by Cheapflights users on 6/18. 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 8/126:12 pm
SJC
- ACK
2 stops17h 29m
Delta
Fri 8/2812:28 pm
ACK
- SJC
2 stops13h 30m
Delta
Deal found 6/18![Delta logo]()
$688
This Delta deal was found by Cheapflights users on 6/18. 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 7/2010:00 pm
SJC
- ACK
2 stops13h 41m
Delta
Mon 7/273:24 pm
ACK
- SJC
2 stops25h 48m
Delta
Deal found 6/18![Delta logo]()
$702
This Delta deal was found by Cheapflights users on 6/18. 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 8/126:12 pm
SJC
- ACK
2 stops17h 29m
Delta
Mon 8/313:24 pm
ACK
- SJC
2 stops22h 12m
Delta
Deal found 6/18![Delta logo]()
$730
Last-minute flights from San Jose to MassachusettsDiscover last-minute flight deals from San Jose to Massachusetts. Data last updated June 23, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Massachusetts. Data last updated June 23, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/20. 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 6/296:20 am
SJC
- BOS
1 stop7h 25m
Delta
Sat 7/410:55 am
BOS
- SJC
1 stop8h 10m
Delta
Deal found 6/20![Delta logo]()
$290
This CheapOair deal was found by Cheapflights users on 6/20. 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.
Mon 6/297:13 am
SJC
- BOS
1 stop19h 27m
Alaska Airlines
Fri 7/34:33 pm
BOS
- SJC
1 stop10h 21m
Alaska Airlines
Deal found 6/20![Alaska Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 6/18. 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 7/37:10 pm
SJC
- BOS
1 stop7h 55m
Delta
Thu 7/94:25 pm
BOS
- SJC
1 stop8h 48m
Delta
Deal found 6/18![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 6/18. 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.
Sat 7/45:01 pm
SJC
- BOS
1 stop10h 04m
Delta
Thu 7/910:55 am
BOS
- SJC
1 stop9h 17m
Delta
Deal found 6/18![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 6/22. 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 7/65:55 pm
SJC
- BOS
1 stop10h 40m
Delta
Thu 7/92:52 pm
BOS
- SJC
1 stop8h 43m
Delta
Deal found 6/22![Delta logo]()
$325
This American Airlines deal was found by Cheapflights users on 6/22. 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.
Thu 7/911:47 am
SJC
- BOS
1 stop9h 12m
American Airlines
Fri 7/177:00 am
BOS
- SJC
1 stop7h 59m
American Airlines
Deal found 6/22![American Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 6/21. 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 7/149:55 am
SJC
- BOS
1 stop10h 25m
Southwest
Tue 7/215:00 am
BOS
- SJC
1 stop10h 25m
Southwest
Deal found 6/21![Southwest logo]()
$322
This American Airlines deal was found by Cheapflights users on 6/20. 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.
Sat 7/186:01 am
SJC
- BDL
2 stops13h 59m
American Airlines
Sat 8/226:00 am
BDL
- SJC
1 stop10h 40m
American Airlines
Deal found 6/20![American Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 6/21. 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 7/187:35 pm
SJC
- BDL
2 stops9h 20m
Southwest
Sat 8/297:55 am
BDL
- SJC
1 stop10h 50m
Southwest
Deal found 6/21![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 6/20. 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.
Tue 7/218:55 am
SJC
- BOS
2 stops10h 50m
Southwest
Tue 7/285:25 am
BOS
- SJC
1 stop9h 55m
Southwest
Deal found 6/20![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 6/19. 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 7/2811:15 am
SJC
- BOS
1 stop9h 05m
Southwest
Wed 7/298:45 am
BOS
- SJC
1 stop13h 30m
Southwest
Deal found 6/19![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 6/19. 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 7/2811:15 am
SJC
- BOS
1 stop9h 05m
Southwest
Tue 8/410:50 am
BOS
- SJC
1 stop10h 30m
Southwest
Deal found 6/19![Southwest logo]()
$310
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 June 23, 2026.
Search for one-way flight options from San Jose to Massachusetts. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/22. 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 7/75:02 pm
SJC
- BOS
1 stop9h 38m
Alaska Airlines
Deal found 6/22![Alaska Airlines logo]()
$153
This Southwest deal was found by Cheapflights users on 6/22. 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 7/2210:40 am
SJC
- BOS
2 stops9h 55m
Southwest
Deal found 6/22![Southwest logo]()
$158
This Delta deal was found by Cheapflights users on 6/19. 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 7/37:10 pm
SJC
- BOS
1 stop7h 55m
Delta
Deal found 6/19![Delta logo]()
$160
This American Airlines deal was found by Cheapflights users on 6/22. 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 7/156:01 am
SJC
- BOS
1 stop10h 19m
American Airlines
Deal found 6/22![American Airlines logo]()
$161
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Sat 9/266:00 am
SJC
- BOS
1 stop8h 10m
American Airlines
Deal found 6/18![American Airlines logo]()
$164
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Thu 7/911:47 am
SJC
- BOS
1 stop9h 12m
American Airlines
Deal found 6/18![American Airlines logo]()
$165
This United Airlines deal was found by Cheapflights users on 6/20. 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.
Mon 7/136:37 pm
SJC
- BOS
2 stops12h 11m
United Airlines
Deal found 6/20![United Airlines logo]()
$166
This Delta deal was found by Cheapflights users on 6/18. 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.
Thu 7/96:35 am
SJC
- BOS
1 stop8h 25m
Delta
Deal found 6/18![Delta logo]()
$167
This United Airlines deal was found by Cheapflights users on 6/20. 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 8/196:37 pm
SJC
- BOS
2 stops12h 11m
United Airlines
Deal found 6/20![United Airlines logo]()
$172
This CheapOair deal was found by Cheapflights users on 6/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:46 pm
SJC
- BOS
1 stop8h 23m
Alaska Airlines
Deal found 6/21![Alaska Airlines logo]()
$173
This United Airlines deal was found by Cheapflights users on 6/18. 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 9/186:37 pm
SJC
- BOS
2 stops12h 41m
United Airlines
Deal found 6/18![United Airlines logo]()
$175
This United Airlines deal was found by Cheapflights users on 6/20. 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.
Mon 8/176:37 pm
SJC
- BOS
2 stops12h 41m
United Airlines
Deal found 6/20![United Airlines logo]()
$177
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 June 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $275 (American Airlines) |
One-way from | $153 (Alaska Airlines) |
Popular in | April |
Cheapest in | October |
Average price | $479 |
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 June 23, 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
Wed 8/12
12:40 pm-1:25 am
1 stop9h 45m
Boston Logan Intl
Fri 8/21
4:25 pm-10:58 pm
1 stop9h 33m
$297
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Mon 8/10
6:10 am-7:15 pm
1 stop10h 05m
Boston Logan Intl
Fri 8/14
5:51 am-12:27 pm
1 stop9h 36m
$297
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Wed 9/23
6:37 pm-8:47 am
2 stops11h 10m
Boston Logan Intl
Fri 9/25
6:00 am-12:01 pm
1 stop9h 01m
$316
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Tue 7/28
5:01 pm-6:05 am
1 stop10h 04m
Boston Logan Intl
Thu 8/6
6:25 am-2:14 pm
1 stop10h 49m
$339
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Wed 7/15
8:55 am-10:45 pm
2 stops10h 50m
Boston Logan Intl
Wed 7/22
3:45 pm-10:30 pm
1 stop9h 45m
$344
San JoseHartford
SJC - BDL
SJCBDL
San Jose
Sat 9/26
11:00 pm-11:20 am
1 stop9h 20m
Hartford Bradley Intl
Tue 10/6
5:35 am-11:20 am
1 stop8h 45m
$355
San JoseHartford
SJC - BDL
SJCBDL
San Jose
Tue 9/8
12:46 pm-11:58 pm
1 stop8h 12m
Hartford Bradley Intl
Wed 9/16
6:00 am-11:36 am
1 stop8h 36m
$355
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Tue 11/17
1:40 pm-11:40 pm
1 stop7h 00m
Boston Logan Intl
Tue 12/1
2:30 pm-9:35 pm
1 stop10h 05m
$357
San JoseHartford
SJC - BDL
SJCBDL
San Jose
Thu 8/20
6:40 am-8:30 pm
1 stop10h 50m
Hartford Bradley Intl
Sat 8/29
6:00 am-11:28 am
1 stop8h 28m
$368
San JoseBoston
SJC - BOS
SJCBOS
San Jose
Sun 7/5
6:37 pm-5:58 am
1 stop8h 21m
Boston Logan Intl
Wed 7/8
8:15 am-5:35 pm
2 stops12h 20m
$384
Showing 1-10 of 55 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
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, December 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 20 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 June 23, 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
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.0
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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San Jose and Massachusetts flights
Browse other San Jose and Massachusetts flight options. Last updated on June 23, 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 June 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$348 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$161 | Average$350 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$250 | Average$476 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$270 | Average$477 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$273 | Average$469 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$297 | Average$402 | FlexibilityNo cancel fee | On-time63% |