$133+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
Jul 15 — Jul 221
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 June 15, 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 June 15, 2026.
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:45 pm
OAK
- BOS
1 stop8h 40m
Southwest
Tue 8/259:05 am
BOS
- OAK
1 stop10h 30m
Southwest
Deal found 6/15![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/1212:45 pm
OAK
- BOS
1 stop8h 40m
Southwest
Wed 8/199:05 am
BOS
- OAK
1 stop10h 30m
Southwest
Deal found 6/11![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/512:45 pm
OAK
- BOS
1 stop8h 40m
Southwest
Tue 8/119:05 am
BOS
- OAK
1 stop10h 30m
Southwest
Deal found 6/11![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 11/47:10 am
OAK
- BOS
1 stop9h 30m
Southwest
Sat 11/79:00 am
BOS
- OAK
1 stop10h 55m
Southwest
Deal found 6/11![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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
Wed 9/29:05 am
BOS
- OAK
1 stop10h 30m
Southwest
Deal found 6/12![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/1112:45 pm
OAK
- BOS
1 stop8h 40m
Southwest
Fri 8/143:55 pm
BOS
- OAK
1 stop10h 10m
Southwest
Deal found 6/12![Southwest logo]()
$296
This CheapOair deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/72:50 pm
OAK
- BOS
1 stop11h 50m
Alaska Airlines
Tue 9/18:00 am
BOS
- OAK
1 stop9h 33m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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
Sat 8/225:50 am
BOS
- OAK
2 stops12h 05m
Southwest
Deal found 6/11![Southwest logo]()
$298
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/95:05 pm
OAK
- BOS
1 stop10h 04m
Delta
Wed 9/162:25 pm
BOS
- OAK
2 stops12h 34m
Delta
Deal found 6/11![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 10/15:25 am
OAK
- ALB
1 stop8h 10m
Southwest
Wed 10/71:20 pm
ALB
- OAK
2 stops10h 50m
Southwest
Deal found 6/11![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/2811:55 pm
OAK
- BDL
1 stop9h 05m
Southwest
Sun 10/47:05 pm
BDL
- OAK
1 stop8h 00m
Southwest
Deal found 6/10![Southwest logo]()
$405
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/811:55 pm
OAK
- BDL
1 stop8h 00m
Southwest
Wed 7/156:30 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 6/12![Southwest logo]()
$408
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 June 15, 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 June 15, 2026.
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:45 pm
OAK
- BOS
1 stop8h 40m
Southwest
Tue 9/15:25 am
BOS
- OAK
2 stops10h 45m
Southwest
Deal found 6/14![Southwest logo]()
$286
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:10 pm
OAK
- BOS
1 stop9h 39m
Alaska Airlines
Tue 9/18:00 am
BOS
- OAK
1 stop9h 33m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 9/95:55 am
OAK
- BOS
2 stops11h 09m
Delta
Wed 9/166:05 am
BOS
- OAK
1 stop8h 44m
Delta
Deal found 6/12![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/265:00 pm
OAK
- BOS
1 stop10h 00m
Southwest
Wed 9/309:05 am
BOS
- OAK
1 stop10h 30m
Southwest
Deal found 6/10![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/114:20 pm
OAK
- BOS
1 stop10h 40m
Southwest
Wed 9/169:05 am
BOS
- OAK
1 stop10h 30m
Southwest
Deal found 6/10![Southwest logo]()
$322
This Alaska Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 9/103:13 pm
OAK
- BOS
1 stop11h 36m
Alaska Airlines
Wed 9/167:59 pm
BOS
- OAK
1 stop16h 28m
Alaska Airlines
Deal found 6/13![Alaska Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/157:35 am
OAK
- BOS
1 stop12h 45m
Southwest
Tue 7/213:45 pm
BOS
- OAK
2 stops10h 40m
Southwest
Deal found 6/11![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:45 pm
OAK
- BOS
1 stop9h 15m
Southwest
Sat 9/125:50 am
BOS
- OAK
2 stops12h 05m
Southwest
Deal found 6/14![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/87:40 pm
OAK
- BDL
2 stops9h 25m
Southwest
Wed 7/156:30 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 6/12![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/217:40 pm
OAK
- BDL
2 stops9h 30m
Southwest
Thu 7/307:10 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 6/11![Southwest logo]()
$421
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/65:03 pm
OAK
- ALB
2 stops12h 53m
Delta
Fri 7/246:05 am
ALB
- OAK
2 stops32h 41m
Delta
Deal found 6/11![Delta logo]()
$721
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/2911:55 pm
OAK
- BDL
1 stop8h 00m
Southwest
Fri 7/317:10 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 6/13![Southwest logo]()
$427
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/75:05 pm
OAK
- ALB
2 stops15h 17m
Delta
Tue 7/219:36 am
ALB
- OAK
2 stops29h 10m
Delta
Deal found 6/10![Delta logo]()
$732
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1911:55 pm
OAK
- BDL
1 stop8h 00m
Southwest
Fri 7/247:10 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 6/15![Southwest logo]()
$453
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1911:55 pm
OAK
- BDL
1 stop8h 00m
Southwest
Thu 7/237:10 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 6/14![Southwest logo]()
$453
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:40 pm
OAK
- BDL
2 stops9h 25m
Southwest
Tue 7/212:35 pm
BDL
- OAK
2 stops10h 55m
Southwest
Deal found 6/14![Southwest logo]()
$455
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/2011:55 pm
OAK
- BDL
1 stop8h 05m
Southwest
Thu 7/3012:40 pm
BDL
- OAK
2 stops13h 00m
Southwest
Deal found 6/10![Southwest logo]()
$458
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/1211:55 pm
OAK
- ALB
1 stop7h 50m
Southwest
Tue 7/211:00 pm
ALB
- OAK
2 stops9h 55m
Southwest
Deal found 6/12![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/105:10 am
OAK
- BDL
2 stops10h 20m
Southwest
Thu 7/167:10 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 6/11![Southwest logo]()
$490
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/311:55 pm
OAK
- ALB
1 stop7h 50m
Southwest
Tue 7/216:55 pm
ALB
- OAK
1 stop7h 40m
Southwest
Deal found 6/10![Southwest logo]()
$517
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/107:40 pm
OAK
- ALB
2 stops9h 20m
Southwest
Fri 7/173:20 pm
ALB
- OAK
2 stops11h 30m
Southwest
Deal found 6/12![Southwest logo]()
$527
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2111:55 pm
OAK
- ALB
1 stop7h 50m
Southwest
Tue 7/283:10 pm
ALB
- OAK
1 stop10h 20m
Southwest
Deal found 6/15![Southwest logo]()
$547
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/1711:55 pm
OAK
- ALB
1 stop12h 45m
Southwest
Mon 7/277:15 pm
ALB
- OAK
1 stop8h 00m
Southwest
Deal found 6/10![Southwest logo]()
$552
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:55 pm
OAK
- ALB
2 stops9h 30m
Southwest
Thu 7/3011:20 am
ALB
- OAK
2 stops10h 45m
Southwest
Deal found 6/14![Southwest logo]()
$557
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1411:55 pm
OAK
- ALB
1 stop7h 50m
Southwest
Sun 8/165:40 am
ALB
- OAK
1 stop7h 30m
Southwest
Deal found 6/13![Southwest logo]()
$587
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/237:40 pm
OAK
- ALB
2 stops9h 45m
Southwest
Fri 7/314:30 pm
ALB
- OAK
2 stops10h 50m
Southwest
Deal found 6/13![Southwest logo]()
$638
Last-minute flights from Oakland to MassachusettsDiscover last-minute flight deals from Oakland to Massachusetts. Data last updated June 15, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Massachusetts. Data last updated June 15, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/35:03 pm
OAK
- BOS
1 stop10h 02m
Delta
Wed 7/86:05 am
BOS
- OAK
1 stop8h 41m
Delta
Deal found 6/10![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/37:40 pm
OAK
- ALB
2 stops9h 15m
Southwest
Tue 7/213:05 pm
ALB
- OAK
2 stops10h 20m
Southwest
Deal found 6/10![Southwest logo]()
$411
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/46:00 am
OAK
- BOS
2 stops11h 10m
Delta
Wed 7/86:05 am
BOS
- OAK
1 stop8h 41m
Delta
Deal found 6/12![Delta logo]()
$302
This CheapOair deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/72:50 pm
OAK
- BOS
1 stop11h 50m
Alaska Airlines
Tue 9/18:00 am
BOS
- OAK
1 stop9h 33m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/77:35 am
OAK
- BOS
1 stop12h 45m
Southwest
Tue 7/144:25 pm
BOS
- OAK
1 stop9h 15m
Southwest
Deal found 6/11![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/811:55 pm
OAK
- BDL
1 stop8h 00m
Southwest
Wed 7/156:30 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 6/12![Southwest logo]()
$408
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/1311:55 pm
OAK
- BOS
1 stop9h 20m
Southwest
Wed 7/154:25 pm
BOS
- OAK
1 stop9h 15m
Southwest
Deal found 6/10![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:05 pm
OAK
- BOS
1 stop10h 00m
Delta
Tue 7/216:05 am
BOS
- OAK
1 stop8h 41m
Delta
Deal found 6/14![Delta logo]()
$312
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/147:40 pm
OAK
- ALB
2 stops9h 25m
Southwest
Tue 7/211:00 pm
ALB
- OAK
2 stops9h 55m
Southwest
Deal found 6/11![Southwest logo]()
$409
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2011:55 pm
OAK
- BOS
1 stop8h 00m
Southwest
Wed 7/294:25 pm
BOS
- OAK
1 stop9h 15m
Southwest
Deal found 6/14![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/217:40 pm
OAK
- BDL
2 stops9h 30m
Southwest
Thu 7/307:10 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 6/11![Southwest logo]()
$421
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/297:40 pm
OAK
- BDL
2 stops9h 25m
Southwest
Fri 7/317:10 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 6/13![Southwest logo]()
$411
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 June 15, 2026.
Search for one-way flight options from Oakland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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
- BOS
1 stop7h 00m
Southwest
Deal found 6/10![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/156:55 pm
OAK
- BOS
1 stop8h 05m
Southwest
Deal found 6/10![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/49:50 am
OAK
- BOS
2 stops9h 55m
Southwest
Deal found 6/10![Southwest logo]()
$138
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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
- ALB
1 stop8h 40m
Southwest
Deal found 6/10![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:40 pm
OAK
- BOS
1 stop7h 45m
Southwest
Deal found 6/14![Southwest logo]()
$149
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/76:49 am
OAK
- BOS
1 stop19h 51m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$154
This CheapOair deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/147:51 pm
OAK
- BOS
1 stop8h 48m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$161
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/35:03 pm
OAK
- BOS
1 stop10h 02m
Delta
Deal found 6/10![Delta logo]()
$164
This CheapOair deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2911:55 am
OAK
- BOS
1 stop15h 14m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$166
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/3110:30 am
OAK
- BOS
2 stops11h 00m
Southwest
Deal found 6/12![Southwest logo]()
$167
This CheapOair deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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.
Sun 7/126:49 am
OAK
- BOS
1 stop19h 51m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$169
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 10/35:03 pm
OAK
- BOS
1 stop10h 27m
Delta
Deal found 6/12![Delta 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 June 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $265 (Southwest) |
One-way from | $133 (Southwest) |
Popular in | June |
Cheapest in | January |
Average price | $506 |
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 June 15, 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
Tue 8/25
12:45 pm-12:25 am
1 stop8h 40m
Boston Logan Intl
Tue 9/1
5:25 am-1:10 pm
2 stops10h 45m
$286
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Sat 9/26
5:00 pm-6:00 am
1 stop10h 00m
Boston Logan Intl
Wed 9/30
9:05 am-4:35 pm
1 stop10h 30m
$295
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Fri 9/11
4:20 pm-6:00 am
1 stop10h 40m
Boston Logan Intl
Wed 9/16
9:05 am-4:35 pm
1 stop10h 30m
$322
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Mon 8/24
5:10 pm-5:49 am
1 stop9h 39m
Boston Logan Intl
Tue 9/1
8:00 am-2:33 pm
1 stop9h 33m
$332
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Wed 9/9
5:55 am-8:04 pm
2 stops11h 09m
Boston Logan Intl
Wed 9/16
6:05 am-11:49 am
1 stop8h 44m
$352
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Wed 7/15
7:35 am-11:20 pm
1 stop12h 45m
Boston Logan Intl
Tue 7/21
3:45 pm-11:25 pm
2 stops10h 40m
$358
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Sat 9/5
5:45 pm-6:00 am
1 stop9h 15m
Boston Logan Intl
Sat 9/12
5:50 am-2:55 pm
2 stops12h 05m
$362
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Thu 9/10
3:13 pm-5:49 am
1 stop11h 36m
Boston Logan Intl
Wed 9/16
7:59 pm-9:27 am
1 stop16h 28m
$372
OaklandHartford
OAK - BDL
OAKBDL
Oakland
Wed 7/8
7:40 pm-8:05 am
2 stops9h 25m
Hartford Bradley Intl
Wed 7/15
6:30 pm-11:35 pm
1 stop8h 05m
$413
OaklandHartford
OAK - BDL
OAKBDL
Oakland
Tue 7/21
7:40 pm-8:10 am
2 stops9h 30m
Hartford Bradley Intl
Thu 7/30
7:10 pm-12:15 am
1 stop8h 05m
$421
Showing 1-10 of 52 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
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
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 June 15, 2026.
Read reviews from past customers who have flown Alaska Airlines,Southwest, andDelta from Oakland to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
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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Complete your trip
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Oakland and Massachusetts flights
Browse other Oakland and Massachusetts flight options. Last updated on June 15, 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 June 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$329 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$149 | Average$363 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$171 | Average$437 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$307 | Average$505 | FlexibilityNo cancel fee | On-time63% |