$152+ Cheap flights from Oakland, CA (OAK) 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
Aug 31 — Sep 71
Round-trip
1 adult, Economy
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Cheapest flights from Oakland to MassachusettsExplore the most affordable flight options available from Oakland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.
Explore the most affordable flight options available from Oakland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.
This Vliegwinkel deal was found by Cheapflights users on 7/31. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:52 pm
OAK
- BOS
1 stop8h 17m
Alaska Airlines
Tue 9/228:00 am
BOS
- OAK
1 stop13h 12m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 7/29. 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 9/811:55 pm
OAK
- ALB
1 stop8h 40m
Southwest
Tue 9/224:15 pm
ALB
- OAK
1 stop9h 15m
Southwest
Deal found 7/29![Southwest logo]()
$311
This Expedia deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:29 pm
OAK
- BOS
1 stop13h 20m
Alaska Airlines
Sat 9/58:00 am
BOS
- OAK
1 stop14h 52m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:10 pm
OAK
- BOS
1 stop9h 39m
Alaska Airlines
Fri 9/46:17 pm
BOS
- OAK
1 stop26h 55m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$323
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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.
Sat 11/76:20 am
OAK
- BOS
1 stop20h 27m
Alaska Airlines
Tue 11/109:00 am
BOS
- OAK
1 stop10h 33m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 7/28. 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 9/2111:55 pm
OAK
- ALB
1 stop8h 40m
Southwest
Thu 9/246:05 pm
ALB
- OAK
1 stop8h 05m
Southwest
Deal found 7/28![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 7/29. 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 9/95:00 pm
OAK
- BOS
1 stop10h 30m
Delta
Wed 9/236:05 am
BOS
- OAK
1 stop8h 54m
Delta
Deal found 7/29![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 7/30. 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 9/109:35 am
OAK
- ALB
2 stops9h 45m
Southwest
Mon 9/146:05 pm
ALB
- OAK
2 stops9h 05m
Southwest
Deal found 7/30![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 7/29. 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 9/1210:55 am
OAK
- BOS
1 stop10h 35m
Southwest
Sat 9/192:10 pm
BOS
- OAK
1 stop12h 45m
Southwest
Deal found 7/29![Southwest logo]()
$342
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:10 pm
OAK
- BOS
1 stop9h 37m
Alaska Airlines
Tue 9/228:00 am
BOS
- OAK
1 stop9h 33m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$344
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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 9/186:48 am
OAK
- BOS
1 stop19h 59m
Alaska Airlines
Mon 9/217:59 pm
BOS
- OAK
1 stop16h 28m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Thu 8/2712:13 pm
OAK
- BDL
1 stop15h 02m
Multiple Airlines
Sun 8/305:40 pm
BDL
- OAK
1 stop20h 38m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$347
Best flights from Oakland to MassachusettsDiscover carefully curated flight deals from Oakland to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
Discover carefully curated flight deals from Oakland to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
This Delta deal was found by Cheapflights users on 7/30. 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 9/95:00 pm
OAK
- BOS
1 stop10h 30m
Delta
Wed 9/162:40 pm
BOS
- OAK
2 stops12h 19m
Delta
Deal found 7/30![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 7/31. 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 9/1511:10 am
OAK
- BOS
1 stop10h 00m
Southwest
Tue 9/225:25 am
BOS
- OAK
2 stops10h 45m
Southwest
Deal found 7/31![Southwest logo]()
$342
This Alaska Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/141:29 pm
OAK
- BOS
1 stop13h 18m
Alaska Airlines
Mon 9/216:17 pm
BOS
- OAK
1 stop19h 49m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 7/31. 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 10/1411:55 pm
OAK
- BDL
1 stop8h 05m
Southwest
Tue 10/203:10 pm
BDL
- OAK
1 stop9h 55m
Southwest
Deal found 7/31![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 7/31. 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 10/305:02 pm
OAK
- BOS
1 stop10h 23m
Delta
Tue 11/34:15 pm
BOS
- OAK
1 stop8h 43m
Delta
Deal found 7/31![Delta logo]()
$354
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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.
Wed 11/186:52 pm
OAK
- BOS
1 stop9h 36m
Alaska Airlines
Mon 11/237:40 am
BOS
- OAK
1 stop10h 35m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 7/29. 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 9/89:30 am
OAK
- ALB
2 stops9h 35m
Southwest
Tue 9/2212:50 pm
ALB
- OAK
2 stops10h 00m
Southwest
Deal found 7/29![Southwest logo]()
$365
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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.
Thu 9/245:10 pm
OAK
- BOS
1 stop9h 37m
Alaska Airlines
Tue 9/298:00 am
BOS
- OAK
1 stop13h 12m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$381
This Southwest deal was found by Cheapflights users on 7/27. 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 8/318:30 pm
OAK
- BOS
2 stops10h 00m
Southwest
Tue 9/89:05 am
BOS
- OAK
1 stop10h 30m
Southwest
Deal found 7/27![Southwest logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 11/56:20 am
OAK
- BOS
1 stop20h 27m
Alaska Airlines
Mon 11/97:02 am
BOS
- OAK
1 stop19h 25m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$401
This Southwest deal was found by Cheapflights users on 7/30. 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 9/312:30 pm
OAK
- BOS
1 stop9h 00m
Southwest
Wed 9/99:25 am
BOS
- OAK
2 stops11h 10m
Southwest
Deal found 7/30![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 7/30. 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 9/141:45 pm
OAK
- BOS
1 stop7h 50m
Southwest
Fri 9/183:55 pm
BOS
- OAK
2 stops11h 15m
Southwest
Deal found 7/30![Southwest logo]()
$374
This Expedia deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:35 pm
OAK
- ACK
2 stops13h 02m
Multiple Airlines
Wed 8/197:00 am
ACK
- OAK
2 stops12h 30m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$1,175
This Southwest deal was found by Cheapflights users on 7/31. 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 10/285:35 am
OAK
- ALB
1 stop6h 50m
Southwest
Sat 10/315:40 am
ALB
- OAK
2 stops11h 05m
Southwest
Deal found 7/31![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 7/28. 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 9/2110:30 am
OAK
- ALB
2 stops9h 10m
Southwest
Thu 9/2411:50 am
ALB
- OAK
2 stops12h 35m
Southwest
Deal found 7/28![Southwest logo]()
$384
This Southwest deal was found by Cheapflights users on 7/31. 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 10/278:10 am
OAK
- ALB
2 stops9h 50m
Southwest
Sat 10/315:40 am
ALB
- OAK
2 stops11h 05m
Southwest
Deal found 7/31![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 7/30. 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 10/185:10 am
OAK
- BOS
2 stops9h 45m
Southwest
Wed 10/212:50 pm
BOS
- OAK
2 stops10h 15m
Southwest
Deal found 7/30![Southwest logo]()
$392
This Southwest deal was found by Cheapflights users on 7/30. 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 8/2710:25 am
OAK
- BDL
2 stops8h 50m
Southwest
Thu 9/38:00 am
BDL
- OAK
2 stops9h 50m
Southwest
Deal found 7/30![Southwest logo]()
$431
This Southwest deal was found by Cheapflights users on 7/29. 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 10/2311:55 pm
OAK
- BDL
1 stop8h 15m
Southwest
Sun 10/257:20 pm
BDL
- OAK
1 stop7h 45m
Southwest
Deal found 7/29![Southwest logo]()
$437
This Southwest deal was found by Cheapflights users on 7/31. 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 10/117:35 pm
OAK
- BDL
2 stops9h 35m
Southwest
Fri 10/167:05 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 7/31![Southwest logo]()
$440
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:40 pm
OAK
- ALB
1 stop7h 20m
Southwest
Sun 11/85:30 am
ALB
- OAK
2 stops10h 45m
Southwest
Deal found 7/27![Southwest logo]()
$442
This Expedia deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:50 pm
OAK
- ACK
2 stops15h 25m
Multiple Airlines
Sat 8/1512:45 pm
ACK
- OAK
2 stops12h 56m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$1,487
This Southwest deal was found by Cheapflights users on 7/31. 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 8/2811:55 pm
OAK
- BDL
1 stop8h 10m
Southwest
Fri 9/411:10 am
BDL
- OAK
2 stops11h 35m
Southwest
Deal found 7/31![Southwest logo]()
$452
This Southwest deal was found by Cheapflights users on 7/27. 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 9/2411:55 pm
OAK
- ALB
1 stop8h 15m
Southwest
Sun 9/275:30 am
ALB
- OAK
1 stop9h 40m
Southwest
Deal found 7/27![Southwest logo]()
$483
This Southwest deal was found by Cheapflights users on 7/28. 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 8/1711:55 pm
OAK
- BDL
1 stop9h 05m
Southwest
Sat 8/221:00 pm
BDL
- OAK
1 stop7h 45m
Southwest
Deal found 7/28![Southwest logo]()
$497
This Expedia deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:50 pm
OAK
- MVY
2 stops20h 14m
Multiple Airlines
Sun 8/1612:55 pm
MVY
- OAK
2 stops12h 46m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$1,925
This Southwest deal was found by Cheapflights users on 7/30. 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 10/71:40 pm
OAK
- BDL
1 stop7h 55m
Southwest
Mon 10/127:05 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 7/30![Southwest logo]()
$526
This Southwest deal was found by Cheapflights users on 7/31. 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 10/87:40 pm
OAK
- ALB
2 stops9h 35m
Southwest
Mon 10/125:30 am
ALB
- OAK
2 stops9h 55m
Southwest
Deal found 7/31![Southwest logo]()
$529
This Southwest deal was found by Cheapflights users on 8/1. 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 9/410:30 am
OAK
- ALB
2 stops9h 10m
Southwest
Mon 9/76:00 am
ALB
- OAK
2 stops9h 30m
Southwest
Deal found 8/1![Southwest logo]()
$554
Last-minute flights from Oakland to MassachusettsDiscover last-minute flight deals from Oakland to Massachusetts. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Massachusetts. Data last updated August 1, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/152:50 pm
OAK
- BOS
1 stop11h 50m
Alaska Airlines
Sat 8/298:00 am
BOS
- OAK
1 stop13h 12m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 7/29. 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 8/1912:45 pm
OAK
- BOS
1 stop8h 40m
Southwest
Fri 8/211:30 pm
BOS
- OAK
1 stop8h 50m
Southwest
Deal found 7/29![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 7/29. 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 8/2210:55 am
OAK
- BOS
1 stop10h 30m
Southwest
Wed 8/263:20 pm
BOS
- OAK
1 stop10h 45m
Southwest
Deal found 7/29![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 7/29. 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 8/269:00 am
OAK
- BOS
2 stops9h 25m
Southwest
Wed 9/23:20 pm
BOS
- OAK
2 stops10h 10m
Southwest
Deal found 7/29![Southwest logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Thu 8/2712:13 pm
OAK
- BDL
1 stop15h 02m
Multiple Airlines
Sun 8/305:40 pm
BDL
- OAK
1 stop20h 38m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 7/30. 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 8/2710:25 am
OAK
- BDL
2 stops8h 50m
Southwest
Thu 9/38:00 am
BDL
- OAK
2 stops9h 50m
Southwest
Deal found 7/30![Southwest logo]()
$431
This Southwest deal was found by Cheapflights users on 7/31. 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 8/2811:55 pm
OAK
- BDL
1 stop8h 10m
Southwest
Fri 9/46:20 pm
BDL
- OAK
1 stop7h 50m
Southwest
Deal found 7/31![Southwest logo]()
$447
This Expedia deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:29 pm
OAK
- BOS
1 stop13h 20m
Alaska Airlines
Sat 9/58:00 am
BOS
- OAK
1 stop14h 52m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:10 pm
OAK
- BOS
1 stop9h 39m
Alaska Airlines
Fri 9/46:17 pm
BOS
- OAK
1 stop26h 55m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$323
This Alaska Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:10 pm
OAK
- BOS
1 stop9h 39m
Alaska Airlines
Sun 9/68:00 am
BOS
- OAK
1 stop13h 12m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 7/27. 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 8/3112:30 pm
OAK
- BOS
1 stop8h 55m
Southwest
Fri 9/411:15 am
BOS
- OAK
1 stop9h 45m
Southwest
Deal found 7/27![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 7/31. 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
OAK
- BOS
1 stop7h 55m
Southwest
Sat 9/53:55 pm
BOS
- OAK
1 stop10h 15m
Southwest
Deal found 7/31![Southwest logo]()
$363
One-way flights from Oakland to MassachusettsSearch for one-way flight options from Oakland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
Search for one-way flight options from Oakland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
This Priceline deal was found by Cheapflights users on 7/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:14 pm
OAK
- BOS
1 stop11h 07m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$152
This Southwest deal was found by Cheapflights users on 7/28. 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 8/2411:55 pm
OAK
- BDL
1 stop9h 05m
Southwest
Deal found 7/28![Southwest logo]()
$156
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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 9/115:10 pm
OAK
- BOS
1 stop9h 37m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Mon 11/98:39 pm
OAK
- BOS
2 stops36h 01m
Frontier
Deal found 7/30![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Sun 9/136:51 pm
OAK
- BOS
2 stops38h 16m
Frontier
Deal found 7/30![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
Sun 9/206:51 pm
OAK
- BOS
2 stops38h 16m
Frontier
Deal found 7/31![Frontier logo]()
$168
This Southwest deal was found by Cheapflights users on 7/28. 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 9/911:10 am
OAK
- BOS
1 stop10h 00m
Southwest
Deal found 7/28![Southwest logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Wed 8/2612:13 pm
OAK
- BOS
2 stops20h 34m
Frontier
Deal found 7/29![Frontier logo]()
$171
This SmartFares deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:10 pm
OAK
- BOS
1 stop9h 37m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$172
This Southwest deal was found by Cheapflights users on 7/31. 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 8/2511:55 pm
OAK
- BDL
1 stop9h 05m
Southwest
Deal found 7/31![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 7/28. 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 9/211:10 am
OAK
- ALB
1 stop7h 50m
Southwest
Deal found 7/28![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 7/28. 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 10/147:30 pm
OAK
- BOS
2 stops9h 40m
Southwest
Deal found 7/28![Southwest logo]()
$174
Find flight deals from Oakland to Massachusetts
Keep the following information in mind while searching for Oakland to Massachusetts flight deals. Data was last updated August 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $303 (Vliegwinkel) |
One-way from | $152 (Priceline) |
Popular in | June |
Cheapest in | January |
Average price | $414 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland 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 August 1, 2026.
Use the filters below to find and compare flights from Oakland to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Wed 9/9
5:00 pm-6:30 am
1 stop10h 30m
Boston Logan Intl
Wed 9/16
2:40 pm-11:59 pm
2 stops12h 19m
$342
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Tue 9/15
11:10 am-12:10 am
1 stop10h 00m
Boston Logan Intl
Tue 9/22
5:25 am-1:10 pm
2 stops10h 45m
$342
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Mon 9/14
1:29 pm-5:47 am
1 stop13h 18m
Boston Logan Intl
Mon 9/21
6:17 pm-11:06 am
1 stop19h 49m
$347
OaklandHartford
OAK - BDL
OAKBDL
Oakland
Wed 10/14
11:55 pm-11:00 am
1 stop8h 05m
Hartford Bradley Intl
Tue 10/20
3:10 pm-10:05 pm
1 stop9h 55m
$347
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Fri 10/30
5:02 pm-6:25 am
1 stop10h 23m
Boston Logan Intl
Tue 11/3
4:15 pm-9:58 pm
1 stop8h 43m
$354
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Wed 11/18
6:52 pm-7:28 am
1 stop9h 36m
Boston Logan Intl
Mon 11/23
7:40 am-3:15 pm
1 stop10h 35m
$359
OaklandAlbany
OAK - ALB
OAKALB
Oakland
Tue 9/8
9:30 am-10:05 pm
2 stops9h 35m
Albany Intl
Tue 9/22
12:50 pm-7:50 pm
2 stops10h 00m
$365
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Mon 8/31
8:30 pm-9:30 am
2 stops10h 00m
Boston Logan Intl
Tue 9/8
9:05 am-4:35 pm
1 stop10h 30m
$373
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Thu 9/3
12:30 pm-12:30 am
1 stop9h 00m
Boston Logan Intl
Wed 9/9
9:25 am-5:35 pm
2 stops11h 10m
$373
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Mon 9/14
1:45 pm-12:35 am
1 stop7h 50m
Boston Logan Intl
Fri 9/18
3:55 pm-12:10 am
2 stops11h 15m
$374
Showing 1-10 of 57 resultsSorted by cheapest first
Best time to book a flight from Oakland to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Oakland with our price prediction graph.
OAK-BOS
OAK-BDL
OAK-ALB
OAK-PVC
OAK-ACK
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 Oakland to Massachusetts
OAK-USMA
OAK-BOS
OAK-BDL
OAK-ALB
OAK-PVC
How much does it cost to fly round-trip from Oakland, California to Massachusetts?
Airfare is below average for this route at the moment.
Oakland, California to Massachusetts flights typically cost between $362 and $777 in September.The cheapest round-trip price found within the last 5 days was $303 on Alaska Airlines (Sep 15-Sep 22).
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 August 1, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andDelta from Oakland to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
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 Oakland to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Oakland to Massachusetts
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Complete your trip
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Find flights from Oakland to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oakland and Massachusetts flights
Browse other Oakland and Massachusetts flight options. Last updated on August 1, 2026.
Popular flight searches
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Oakland to Massachusetts flights
Consider these flights traveling from Oakland to Massachusetts.
Top 4 airlines flying from Oakland to Massachusetts
Discover the top 4 airlines that operate flights from Oakland 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 August 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$358 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$208 | Average$437 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$233 | Average$484 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$343 | Average$499 | FlexibilityNo cancel fee | On-time63% |