$127+ Cheap flights from Oakland, CA (OAK) to Massachusetts
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
Oct 17 — Oct 241
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 September 17, 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 September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/13. 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 10/281:40 pm -
1 stop7h 15m
Wed 11/45:55 pm -
1 stop8h 40m
Deal found 9/13![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 9/14. 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 11/22:40 pm -
1 stop7h 30m
Wed 11/48:25 am -
1 stop11h 10m
Deal found 9/14![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 10/2912:35 pm -
1 stop9h 40m
Sat 10/315:30 am -
2 stops11h 00m
Deal found 9/15![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2611:55 pm -
1 stop8h 15m
Thu 10/2910:50 am -
1 stop11h 45m
Deal found 9/14![Southwest logo]()
$287
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:05 pm -
1 stop9h 16m
Wed 10/217:51 am -
1 stop9h 43m
Deal found 9/15![Alaska Airlines logo]()
$291
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/207:53 pm -
1 stop8h 33m
Thu 10/227:51 am -
1 stop9h 43m
Deal found 9/16![Alaska Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 9/14. 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 11/76:25 am -
1 stop8h 40m
Sat 11/1410:40 am -
2 stops11h 15m
Deal found 9/14![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 10/2311:55 pm -
1 stop8h 15m
Wed 10/283:10 pm -
1 stop10h 00m
Deal found 9/15![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 9/14. 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 10/147:30 pm -
2 stops9h 40m
Wed 10/211:25 pm -
1 stop12h 55m
Deal found 9/14![Southwest logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/55:55 pm -
1 stop9h 20m
Sun 11/85:51 pm -
1 stop26h 09m
Deal found 9/16![Multiple Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 9/14. 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 12/106:30 am -
1 stop6h 55m
Sat 12/127:40 am -
1 stop10h 55m
Deal found 9/14![Southwest logo]()
$370
This Southwest deal was found by Cheapflights users on 9/12. 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 11/1111:50 pm -
1 stop8h 20m
Mon 11/166:25 pm -
1 stop8h 10m
Deal found 9/12![Southwest logo]()
$439
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 September 17, 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 September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 10/2311:55 pm -
2 stops8h 55m
Wed 10/283:10 pm -
1 stop10h 00m
Deal found 9/15![Southwest logo]()
$318
This Delta deal was found by Cheapflights users on 9/14. 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.
Sat 11/75:02 pm -
2 stops13h 42m
Sat 11/146:05 am -
2 stops13h 12m
Deal found 9/14![Delta logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:12 am -
1 stop20h 34m
Mon 11/166:09 pm -
1 stop29h 51m
Deal found 9/15![Alaska Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 9/15. 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 10/137:35 pm -
2 stops10h 15m
Tue 10/205:25 am -
1 stop8h 10m
Deal found 9/15![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 9/14. 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 10/177:55 am -
1 stop9h 20m
Tue 10/274:20 pm -
1 stop10h 00m
Deal found 9/14![Southwest logo]()
$336
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:12 pm -
2 stops19h 57m
Sun 11/151:30 pm -
2 stops27h 34m
Deal found 9/14![Multiple Airlines logo]()
$754
This Delta deal was found by Cheapflights users on 9/12. 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 10/175:02 pm -
1 stop10h 28m
Tue 10/206:05 am -
1 stop8h 56m
Deal found 9/12![Delta logo]()
$403
This Alaska Airlines deal was found by Cheapflights users on 9/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:14 pm -
1 stop11h 07m
Fri 10/237:51 am -
1 stop9h 43m
Deal found 9/12![Alaska Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 11/132:40 pm -
1 stop7h 35m
Sun 11/154:20 pm -
1 stop11h 20m
Deal found 9/14![Southwest logo]()
$386
This Alaska Airlines deal was found by Cheapflights users on 9/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/266:03 am -
1 stop8h 00m
Thu 1/286:14 pm -
1 stop27h 11m
Deal found 9/12![Alaska Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 9/12. 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 12/236:35 pm -
2 stops10h 20m
Wed 1/131:00 pm -
2 stops10h 20m
Deal found 9/12![Southwest logo]()
$451
This Alaska Airlines deal was found by Cheapflights users on 9/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:14 pm -
1 stop11h 07m
Tue 10/207:51 am -
1 stop9h 43m
Deal found 9/12![Alaska Airlines logo]()
$504
This Delta deal was found by Cheapflights users on 9/12. 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.
Tue 12/225:56 am -
2 stops14h 42m
Tue 1/122:20 pm -
2 stops12h 36m
Deal found 9/12![Delta logo]()
$578
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/611:50 pm -
1 stop8h 25m
Sun 11/86:40 pm -
1 stop9h 00m
Deal found 9/16![Southwest logo]()
$463
This Alaska Airlines deal was found by Cheapflights users on 9/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/49:59 am -
1 stop16h 22m
Tue 10/66:40 pm -
1 stop19h 45m
Deal found 9/12![Alaska Airlines logo]()
$518
This Delta deal was found by Cheapflights users on 9/12. 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.
Thu 12/245:56 am -
2 stops29h 15m
Wed 1/131:00 pm -
2 stops13h 56m
Deal found 9/12![Delta logo]()
$592
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:12 pm -
2 stops19h 57m
Thu 11/197:30 am -
2 stops34h 45m
Deal found 9/14![Multiple Airlines logo]()
$760
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/211:55 pm -
1 stop8h 20m
Tue 10/64:10 pm -
2 stops10h 10m
Deal found 9/16![Southwest logo]()
$501
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:12 pm -
2 stops19h 57m
Fri 11/207:30 am -
2 stops37h 45m
Deal found 9/14![Multiple Airlines logo]()
$805
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:50 pm -
2 stops10h 15m
Sat 10/175:25 am -
2 stops10h 00m
Deal found 9/17![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 9/12. 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.
Tue 12/225:56 am -
2 stops14h 42m
Thu 1/145:00 pm -
2 stops9h 56m
Deal found 9/12![Delta logo]()
$720
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 12/185:50 am -
1 stop8h 30m
Fri 12/256:25 pm -
1 stop8h 05m
Deal found 9/14![Southwest logo]()
$527
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:12 pm -
2 stops43h 57m
Sun 11/151:30 pm -
2 stops27h 34m
Deal found 9/14![Multiple Airlines logo]()
$878
This Southwest deal was found by Cheapflights users on 9/12. 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 10/137:35 pm -
2 stops9h 50m
Sat 10/1712:55 pm -
2 stops11h 35m
Deal found 9/12![Southwest logo]()
$528
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/102:44 pm -
2 stops47h 25m
Sat 11/147:30 am -
2 stops33h 34m
Deal found 9/14![Multiple Airlines logo]()
$878
This Southwest deal was found by Cheapflights users on 9/15. 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 10/147:35 pm -
2 stops9h 40m
Mon 10/197:15 pm -
1 stop8h 00m
Deal found 9/15![Southwest logo]()
$532
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 11/2012:15 pm -
2 stops9h 50m
Sat 11/216:40 pm -
1 stop8h 35m
Deal found 9/15![Southwest logo]()
$533
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 11/206:30 pm -
2 stops10h 20m
Sun 11/2212:55 pm -
2 stops11h 20m
Deal found 9/14![Southwest logo]()
$536
This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:53 pm -
2 stops12h 27m
Fri 10/169:52 am -
2 stops16h 03m
Deal found 9/13![Multiple Airlines logo]()
$1,236
This Southwest deal was found by Cheapflights users on 9/12. 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 9/2711:55 pm -
2 stops9h 45m
Thu 10/17:15 pm -
1 stop7h 55m
Deal found 9/12![Southwest logo]()
$612
Last-minute flights from Oakland to MassachusettsDiscover last-minute flight deals from Oakland to Massachusetts. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Massachusetts. Data last updated September 17, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/211:55 pm -
1 stop8h 20m
Tue 10/66:25 pm -
1 stop7h 55m
Deal found 9/16![Southwest logo]()
$496
This Southwest deal was found by Cheapflights users on 9/14. 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 10/147:30 pm -
2 stops9h 40m
Wed 10/211:25 pm -
1 stop12h 55m
Deal found 9/14![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/14. 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 10/157:40 pm -
2 stops9h 30m
Thu 10/227:05 pm -
1 stop8h 10m
Deal found 9/14![Southwest logo]()
$488
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:05 pm -
1 stop9h 16m
Wed 10/217:51 am -
1 stop9h 43m
Deal found 9/15![Alaska Airlines logo]()
$291
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/207:53 pm -
1 stop8h 33m
Thu 10/227:51 am -
1 stop9h 43m
Deal found 9/16![Alaska Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
2 stops11h 15m
Wed 10/212:40 pm -
2 stops12h 16m
Deal found 9/15![Delta logo]()
$307
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/206:00 am -
2 stops11h 15m
Wed 10/2811:15 am -
1 stop8h 07m
Deal found 9/16![Delta logo]()
$321
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/2112:41 pm -
1 stop8h 18m
Wed 10/282:40 pm -
2 stops12h 16m
Deal found 9/16![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 10/2311:55 pm -
1 stop8h 15m
Wed 10/283:10 pm -
1 stop10h 00m
Deal found 9/15![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2611:55 pm -
1 stop8h 15m
Thu 10/2910:50 am -
1 stop11h 45m
Deal found 9/14![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/13. 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 10/281:40 pm -
1 stop7h 15m
Wed 11/45:55 pm -
1 stop8h 40m
Deal found 9/13![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 10/2912:35 pm -
1 stop9h 40m
Sat 10/315:30 am -
2 stops11h 00m
Deal found 9/15![Southwest logo]()
$276
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 September 17, 2026.
Search for one-way flight options from Oakland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/15. 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 10/286:00 am -
1 stop8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:45 pm -
2 stops9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 9/15. 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 10/137:35 pm -
2 stops10h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$144
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/15:07 pm -
1 stop10h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$149
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am -
2 stops10h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$154
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/165:05 pm -
1 stop10h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$168
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:55 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$169
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:05 pm -
1 stop9h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Alaska Airlines logo]()
$174
This Southwest deal was found by Cheapflights users on 9/13. 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.
Mon 2/111:50 pm -
1 stop8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
2 stops11h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Delta logo]()
$179
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/235:05 pm -
1 stop9h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Alaska Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 9/15. 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.
Mon 10/57:40 pm -
2 stops9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$183
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $254 (Southwest) |
One-way from | $127 (Southwest) |
Popular in | June |
Cheapest in | January |
Average price | $434 |
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 7,457,451 searches. Data last updated September 17, 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
OaklandHartford
OAK Oakland - BDL Hartford Bradley Intl
OAKBDL
Oakland
Tue 11/10
7:45 pm-7:55 am
2 stops9h 10m
Hartford Bradley Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$128
OaklandBoston
OAK Oakland - BOS Boston Logan Intl
OAKBOS
Oakland
Thu 11/5
6:20 am-5:50 pm
1 stop8h 30m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$144
OaklandBoston
OAK Oakland - BOS Boston Logan Intl
OAKBOS
Oakland
Thu 2/4
6:40 am-6:25 pm
2 stops8h 45m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$149
OaklandHartford
OAK Oakland - BDL Hartford Bradley Intl
OAKBDL
Oakland
Mon 2/1
7:20 pm-7:55 am
2 stops9h 35m
Hartford Bradley Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$182
OaklandBoston
OAK Oakland - BOS Boston Logan Intl
OAKBOS
Oakland
Wed 9/30
12:39 pm-11:53 pm
1 stop8h 14m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$194
OaklandHartford
OAK Oakland - BDL Hartford Bradley Intl
OAKBDL
Oakland
Tue 11/10
12:48 pm-11:42 pm
3 stops31h 54m
Hartford Bradley Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$212
OaklandBoston
OAK Oakland - BOS Boston Logan Intl
OAKBOS
Oakland
Sat 10/10
6:50 pm-8:05 am
2 stops10h 15m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$225
OaklandBoston
OAK Oakland - BOS Boston Logan Intl
OAKBOS
Oakland
Wed 12/30
7:25 pm-6:45 am
1 stop8h 20m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$225
OaklandBoston
OAK Oakland - BOS Boston Logan Intl
OAKBOS
Oakland
Tue 12/1
7:50 pm-8:20 am
2 stops9h 30m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$230
OaklandHartford
OAK Oakland - BDL Hartford Bradley Intl
OAKBDL
Oakland
Fri 11/27
5:35 am-3:45 pm
1 stop7h 10m
Hartford Bradley Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$232
Showing 1-10 of 59 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-BDL
OAK-BOS
OAK-PVC
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-BDL
OAK-BOS
OAK-PVC
OAK-ALB
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 $382 and $473 in October.The cheapest round-trip price found within the last 5 days was $254 on Southwest (Oct 28-Nov 4).
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 September 17, 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.
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
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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 September 17, 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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$233 | Average$513 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$278 | Average$452 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$292 | Average$358 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$343 | Average$499 | FlexibilityNo cancel fee | On-time63% |