$149+ 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
mai 30 — juin 61
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 avril 30, 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 avril 30, 2026.
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mar. 6/25:05 pm
OAK
- BOS
1 stop10h 15m
Delta
sam. 6/66:10 am
BOS
- OAK
1 stop8h 38m
Delta
Deal found 4/25![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/235:55 pm
OAK
- BOS
1 stop9h 25m
Delta
mer. 5/272:33 pm
BOS
- OAK
2 stops12h 24m
Delta
Deal found 4/28![Delta logo]()
$302
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/307:03 pm
OAK
- BOS
1 stop8h 17m
Alaska Airlines
sam. 6/68:05 am
BOS
- OAK
1 stop9h 09m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 4/28. 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.
mar. 8/44:35 pm
OAK
- BOS
1 stop10h 25m
Southwest
mer. 8/192:45 pm
BOS
- OAK
2 stops11h 20m
Southwest
Deal found 4/28![Southwest logo]()
$312
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/272:58 pm
OAK
- BOS
1 stop11h 46m
Alaska Airlines
lun. 6/16:40 pm
BOS
- OAK
1 stop18h 05m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$322
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 8/96:49 am
OAK
- BOS
1 stop19h 51m
Alaska Airlines
ven. 8/144:33 pm
BOS
- OAK
1 stop9h 08m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$327
This Expedia deal was found by Cheapflights users on 4/27. 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.
sam. 5/169:30 am
OAK
- BOS
1 stop17h 50m
Alaska Airlines
sam. 5/236:40 pm
BOS
- OAK
1 stop18h 05m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mar. 7/79:50 am
OAK
- BOS
1 stop10h 10m
Southwest
jeu. 7/234:30 pm
BOS
- OAK
1 stop9h 00m
Southwest
Deal found 4/25![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/225:05 pm
OAK
- BOS
1 stop10h 04m
Delta
mar. 8/256:00 am
BOS
- OAK
1 stop9h 24m
Delta
Deal found 4/28![Delta logo]()
$338
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/268:15 pm
OAK
- BOS
1 stop30h 29m
Alaska Airlines
mar. 6/28:05 am
BOS
- OAK
1 stop9h 09m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$340
This Expedia deal was found by Cheapflights users on 4/28. 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.
lun. 6/16:02 am
OAK
- BOS
1 stop20h 42m
Alaska Airlines
lun. 8/316:10 pm
BOS
- OAK
1 stop19h 34m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 6/65:55 pm
OAK
- BDL
2 stops11h 55m
Delta
jeu. 8/201:00 pm
BDL
- OAK
2 stops13h 49m
Delta
Deal found 4/27![Delta logo]()
$346
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 avril 30, 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 avril 30, 2026.
This Delta deal was found by Cheapflights users on 4/29. 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.
sam. 5/235:55 pm
OAK
- BOS
1 stop9h 25m
Delta
mer. 5/276:10 am
BOS
- OAK
1 stop8h 38m
Delta
Deal found 4/29![Delta logo]()
$297
This Alaska Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mer. 6/32:58 pm
OAK
- BOS
1 stop11h 46m
Alaska Airlines
sam. 6/68:05 am
BOS
- OAK
1 stop9h 09m
Alaska Airlines
Deal found 4/25![Alaska Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
lun. 6/111:55 pm
OAK
- BDL
1 stop7h 45m
Southwest
lun. 6/87:10 pm
BDL
- OAK
1 stop8h 00m
Southwest
Deal found 4/26![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mar. 9/2211:55 pm
OAK
- ALB
1 stop8h 40m
Southwest
mar. 9/296:20 pm
ALB
- OAK
1 stop7h 45m
Southwest
Deal found 4/25![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 6/135:38 pm
OAK
- BOS
1 stop9h 27m
Delta
ven. 6/192:13 pm
BOS
- OAK
2 stops12h 41m
Delta
Deal found 4/28![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 4/29. 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.
lun. 7/1312:15 pm
OAK
- BOS
1 stop7h 45m
Southwest
lun. 7/2010:15 pm
BOS
- OAK
2 stops15h 35m
Southwest
Deal found 4/29![Southwest logo]()
$368
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
dim. 8/210:37 am
OAK
- BOS
1 stop16h 03m
Alaska Airlines
mar. 8/114:33 pm
BOS
- OAK
1 stop9h 08m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mar. 6/26:00 am
OAK
- BOS
2 stops11h 04m
Delta
sam. 6/66:10 am
BOS
- OAK
1 stop8h 38m
Delta
Deal found 4/25![Delta logo]()
$392
This Southwest deal was found by Cheapflights users on 4/27. 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.
mar. 7/147:40 pm
OAK
- BOS
2 stops9h 20m
Southwest
ven. 7/175:30 pm
BOS
- OAK
1 stop9h 15m
Southwest
Deal found 4/27![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 4/29. 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.
lun. 8/1711:55 pm
OAK
- ALB
1 stop8h 40m
Southwest
ven. 8/216:05 pm
ALB
- OAK
1 stop8h 00m
Southwest
Deal found 4/29![Southwest logo]()
$385
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/226:00 am
OAK
- BOS
2 stops11h 01m
Delta
jeu. 5/282:33 pm
BOS
- OAK
2 stops12h 24m
Delta
Deal found 4/27![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 4/29. 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.
sam. 5/237:50 pm
OAK
- BOS
2 stops10h 30m
Southwest
jeu. 5/283:45 pm
BOS
- OAK
1 stop11h 40m
Southwest
Deal found 4/29![Southwest logo]()
$393
This Southwest deal was found by Cheapflights users on 4/27. 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.
dim. 7/127:15 pm
OAK
- BDL
2 stops9h 50m
Southwest
mar. 7/144:00 pm
BDL
- OAK
2 stops10h 20m
Southwest
Deal found 4/27![Southwest logo]()
$400
This Southwest deal was found by Cheapflights users on 4/29. 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.
ven. 7/2412:15 pm
OAK
- BOS
1 stop7h 45m
Southwest
lun. 7/2710:15 pm
BOS
- OAK
2 stops15h 35m
Southwest
Deal found 4/29![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 4/27. 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.
mar. 5/197:35 pm
OAK
- BDL
2 stops9h 35m
Southwest
sam. 6/67:55 am
BDL
- OAK
2 stops14h 25m
Southwest
Deal found 4/27![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 4/27. 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.
ven. 6/59:05 pm
OAK
- BDL
2 stops10h 50m
Southwest
mar. 6/97:05 am
BDL
- OAK
2 stops13h 00m
Southwest
Deal found 4/27![Southwest logo]()
$409
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mer. 8/1211:55 pm
OAK
- BDL
2 stops10h 05m
Southwest
jeu. 8/136:20 pm
BDL
- OAK
1 stop7h 45m
Southwest
Deal found 4/25![Southwest logo]()
$423
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
jeu. 8/2011:55 pm
OAK
- ALB
1 stop8h 15m
Southwest
dim. 8/235:40 am
ALB
- OAK
1 stop7h 30m
Southwest
Deal found 4/26![Southwest logo]()
$458
This Southwest deal was found by Cheapflights users on 4/29. 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.
ven. 5/297:30 pm
OAK
- ALB
2 stops9h 30m
Southwest
lun. 6/15:50 am
ALB
- OAK
2 stops10h 30m
Southwest
Deal found 4/29![Southwest logo]()
$459
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
jeu. 9/39:30 am
OAK
- BDL
2 stops9h 40m
Southwest
dim. 9/67:50 am
BDL
- OAK
1 stop8h 25m
Southwest
Deal found 4/25![Southwest logo]()
$465
This Southwest deal was found by Cheapflights users on 4/29. 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.
lun. 9/2811:55 pm
OAK
- BDL
1 stop9h 05m
Southwest
dim. 10/41:10 pm
BDL
- OAK
2 stops10h 00m
Southwest
Deal found 4/29![Southwest logo]()
$503
This Southwest deal was found by Cheapflights users on 4/29. 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.
ven. 8/1411:55 pm
OAK
- BDL
1 stop8h 10m
Southwest
dim. 8/161:00 pm
BDL
- OAK
1 stop12h 30m
Southwest
Deal found 4/29![Southwest logo]()
$523
This Southwest deal was found by Cheapflights users on 4/29. 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.
ven. 6/59:05 pm
OAK
- BDL
2 stops10h 50m
Southwest
dim. 6/75:05 pm
BDL
- OAK
2 stops10h 40m
Southwest
Deal found 4/29![Southwest logo]()
$537
This Southwest deal was found by Cheapflights users on 4/27. 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.
ven. 6/197:45 pm
OAK
- BDL
2 stops9h 25m
Southwest
lun. 6/225:10 pm
BDL
- OAK
2 stops10h 05m
Southwest
Deal found 4/27![Southwest logo]()
$557
This Southwest deal was found by Cheapflights users on 4/29. 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.
jeu. 7/29:05 pm
OAK
- BDL
2 stops10h 50m
Southwest
dim. 7/55:35 am
BDL
- OAK
2 stops9h 40m
Southwest
Deal found 4/29![Southwest logo]()
$571
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
jeu. 7/25:45 am
OAK
- ALB
1 stop8h 30m
Southwest
mar. 7/71:00 pm
ALB
- OAK
2 stops9h 55m
Southwest
Deal found 4/25![Southwest logo]()
$573
This Southwest deal was found by Cheapflights users on 4/27. 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.
mar. 5/127:35 pm
OAK
- ALB
2 stops9h 20m
Southwest
sam. 5/1612:35 pm
ALB
- OAK
2 stops11h 40m
Southwest
Deal found 4/27![Southwest logo]()
$587
This Southwest deal was found by Cheapflights users on 4/27. 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.
mer. 6/37:35 pm
OAK
- ALB
2 stops9h 50m
Southwest
dim. 6/75:00 pm
ALB
- OAK
2 stops10h 45m
Southwest
Deal found 4/27![Southwest logo]()
$589
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mer. 7/297:55 pm
OAK
- ALB
2 stops9h 30m
Southwest
sam. 8/13:55 pm
ALB
- OAK
2 stops10h 15m
Southwest
Deal found 4/25![Southwest logo]()
$589
This Southwest deal was found by Cheapflights users on 4/28. 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.
ven. 6/1911:55 pm
OAK
- ALB
1 stop12h 45m
Southwest
dim. 6/2812:15 pm
ALB
- OAK
2 stops9h 50m
Southwest
Deal found 4/28![Southwest logo]()
$589
Last-minute flights from Oakland to MassachusettsDiscover last-minute flight deals from Oakland to Massachusetts. Data last updated avril 30, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Massachusetts. Data last updated avril 30, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/27. 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.
sam. 5/169:30 am
OAK
- BOS
1 stop17h 50m
Alaska Airlines
sam. 5/236:40 pm
BOS
- OAK
1 stop18h 05m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/235:55 pm
OAK
- BOS
1 stop9h 25m
Delta
mer. 5/272:33 pm
BOS
- OAK
2 stops12h 24m
Delta
Deal found 4/28![Delta logo]()
$302
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/235:55 pm
OAK
- BOS
1 stop9h 25m
Delta
jeu. 5/282:33 pm
BOS
- OAK
2 stops12h 24m
Delta
Deal found 4/28![Delta logo]()
$327
This Expedia deal was found by Cheapflights users on 4/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/238:15 pm
OAK
- BOS
1 stop16h 33m
Alaska Airlines
jeu. 5/288:05 am
BOS
- OAK
1 stop9h 09m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$347
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/268:15 pm
OAK
- BOS
1 stop30h 29m
Alaska Airlines
mar. 6/28:05 am
BOS
- OAK
1 stop9h 09m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$340
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/2710:29 am
OAK
- BOS
1 stop16h 15m
Alaska Airlines
mer. 6/36:40 pm
BOS
- OAK
1 stop18h 05m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$297
This CheapOair deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
mer. 5/272:58 pm
OAK
- BOS
1 stop11h 46m
Alaska Airlines
jeu. 6/114:33 pm
BOS
- OAK
1 stop9h 08m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$317
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/272:58 pm
OAK
- BOS
1 stop11h 46m
Alaska Airlines
lun. 6/16:40 pm
BOS
- OAK
1 stop18h 05m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$322
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/276:02 am
OAK
- BOS
1 stop20h 42m
Alaska Airlines
sam. 5/306:00 am
BOS
- OAK
2 stops15h 21m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$345
This Expedia deal was found by Cheapflights users on 4/27. 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.
mer. 5/276:02 am
OAK
- BOS
1 stop20h 42m
Alaska Airlines
mar. 6/26:00 am
BOS
- OAK
2 stops15h 21m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/285:05 pm
OAK
- BOS
1 stop10h 15m
Delta
jeu. 6/42:33 pm
BOS
- OAK
2 stops12h 24m
Delta
Deal found 4/27![Delta logo]()
$352
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/307:03 pm
OAK
- BOS
1 stop8h 17m
Alaska Airlines
sam. 6/68:05 am
BOS
- OAK
1 stop9h 09m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$307
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 avril 30, 2026.
Search for one-way flight options from Oakland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated avril 30, 2026.
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/235:55 pm
OAK
- BOS
1 stop9h 25m
Delta
Deal found 4/27![Delta logo]()
$149
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/2710:29 am
OAK
- BOS
1 stop16h 15m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$154
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/307:03 pm
OAK
- BOS
1 stop8h 17m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$159
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
sam. 5/235:55 pm
OAK
- BDL
2 stops13h 58m
Delta
Deal found 4/26![Delta logo]()
$161
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/106:49 am
OAK
- BOS
1 stop19h 51m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$164
This Southwest deal was found by Cheapflights users on 4/28. 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.
lun. 7/2011:55 pm
OAK
- BOS
1 stop9h 20m
Southwest
Deal found 4/28![Southwest logo]()
$169
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 6/65:55 pm
OAK
- ALB
2 stops11h 59m
Delta
Deal found 4/27![Delta logo]()
$172
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 6/116:49 am
OAK
- BOS
1 stop19h 51m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$174
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/16:02 am
OAK
- BOS
1 stop20h 42m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 4/27. 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.
mar. 8/1811:55 pm
OAK
- BDL
1 stop9h 05m
Southwest
Deal found 4/27![Southwest logo]()
$181
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/1310:35 am
OAK
- BOS
1 stop10h 24m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$184
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 7/155:05 pm
OAK
- BDL
2 stops12h 44m
Delta
Deal found 4/27![Delta logo]()
$186
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 avril 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $297 (Delta) |
One-way from | $149 (Delta) |
Popular in | April |
Cheapest in | January |
Average price | $467 |
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 avril 30, 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
sam. 5/23
5:55 pm-6:20 am
1 stop9h 25m
Boston Logan Intl
mer. 5/27
6:10 am-11:48 am
1 stop8h 38m
$297
OaklandBoston
OAK - BOS
OAKBOS
Oakland
mer. 6/3
2:58 pm-5:44 am
1 stop11h 46m
Boston Logan Intl
sam. 6/6
8:05 am-2:14 pm
1 stop9h 09m
$340
Quickest round-trip
OaklandHartford
OAK - BDL
OAKBDL
Oakland
lun. 6/1
11:55 pm-10:40 am
1 stop7h 45m
Hartford Bradley Intl
lun. 6/8
7:10 pm-12:10 am
1 stop8h 00m
$359
OaklandAlbany
OAK - ALB
OAKALB
Oakland
mar. 9/22
11:55 pm-11:35 am
1 stop8h 40m
Albany Intl
mar. 9/29
6:20 pm-11:05 pm
1 stop7h 45m
$359
OaklandBoston
OAK - BOS
OAKBOS
Oakland
lun. 7/13
12:15 pm-11:00 pm
1 stop7h 45m
Boston Logan Intl
lun. 7/20
10:15 pm-10:50 am
2 stops15h 35m
$368
OaklandBoston
OAK - BOS
OAKBOS
Oakland
mar. 7/14
7:40 pm-8:00 am
2 stops9h 20m
Boston Logan Intl
ven. 7/17
5:30 pm-11:45 pm
1 stop9h 15m
$372
OaklandBoston
OAK - BOS
OAKBOS
Oakland
sam. 6/13
5:38 pm-6:05 am
1 stop9h 27m
Boston Logan Intl
ven. 6/19
2:13 pm-11:54 pm
2 stops12h 41m
$383
OaklandAlbany
OAK - ALB
OAKALB
Oakland
lun. 8/17
11:55 pm-11:35 am
1 stop8h 40m
Albany Intl
ven. 8/21
6:05 pm-11:05 pm
1 stop8h 00m
$385
OaklandBoston
OAK - BOS
OAKBOS
Oakland
mar. 6/2
6:00 am-8:04 pm
2 stops11h 04m
Boston Logan Intl
sam. 6/6
6:10 am-11:48 am
1 stop8h 38m
$392
OaklandBoston
OAK - BOS
OAKBOS
Oakland
sam. 5/23
7:50 pm-9:20 am
2 stops10h 30m
Boston Logan Intl
jeu. 5/28
3:45 pm-12:25 am
1 stop11h 40m
$393
Showing 1-10 of 60 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-MVY
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-MVY
What is the cheapest month to book a flight from Oakland, California to Massachusetts?
Currently, September is the cheapest month in which you can book a flight from Oakland, California to Massachusetts (average of $98). Flying from Oakland, California to Massachusetts in March is currently the most expensive (average of $602). 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 Oakland, California to Massachusetts?
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 avril 30, 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.
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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 avril 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 avril 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$149 | Average$327 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$171 | Average$417 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$267 | Average$459 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$307 | Average$461 | FlexibilityNo cancel fee | On-time63% |