$146+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
Apr 19 — Apr 261
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Oakland to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Oakland to Massachusetts
Cheapest
Best
Last-minute
One-way
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 March 20, 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 March 20, 2026.
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:35 pm
OAK
- BDL
2 stops9h 35m
Southwest
Tue 5/126:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/18![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 3/17. 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.
Wed 4/2211:55 pm
OAK
- BDL
1 stop7h 45m
Southwest
Mon 4/277:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/17![Southwest logo]()
$301
This CheapOair deal was found by Cheapflights users on 3/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:03 pm
OAK
- BOS
1 stop8h 17m
Alaska Airlines
Tue 6/167:36 pm
BOS
- OAK
1 stop16h 50m
Alaska Airlines
Deal found 3/17![Alaska Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 3/15. 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 6/211:55 pm
OAK
- BDL
1 stop7h 45m
Southwest
Wed 6/36:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/15![Southwest logo]()
$311
This CheapOair deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:01 pm
OAK
- BOS
1 stop15h 40m
Alaska Airlines
Tue 6/167:36 pm
BOS
- OAK
1 stop16h 50m
Alaska Airlines
Deal found 3/19![Alaska Airlines logo]()
$312
This CheapOair deal was found by Cheapflights users on 3/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:20 am
OAK
- BOS
1 stop14h 39m
Alaska Airlines
Wed 5/69:00 am
BOS
- OAK
1 stop16h 32m
Alaska Airlines
Deal found 3/17![Alaska Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:34 pm
OAK
- BOS
1 stop8h 23m
Delta
Wed 4/222:48 pm
BOS
- OAK
2 stops12h 06m
Delta
Deal found 3/18![Delta logo]()
$322
This Southwest deal was found by Cheapflights users on 3/16. 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 4/285:50 am
OAK
- BDL
1 stop7h 10m
Southwest
Fri 5/17:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/16![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 3/17. 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.
Wed 4/295:50 am
OAK
- BOS
1 stop7h 15m
Southwest
Wed 5/134:45 pm
BOS
- OAK
1 stop8h 20m
Southwest
Deal found 3/17![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 3/15. 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 3/3111:55 pm
OAK
- BOS
1 stop8h 25m
Southwest
Tue 4/76:20 pm
BOS
- OAK
1 stop8h 05m
Southwest
Deal found 3/15![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 3/15. 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.
Mon 5/45:04 pm
OAK
- BDL
2 stops14h 39m
Delta
Wed 5/63:00 pm
BDL
- OAK
2 stops11h 54m
Delta
Deal found 3/15![Delta logo]()
$334
This Southwest deal was found by Cheapflights users on 3/15. 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 4/2911:55 pm
OAK
- BDL
1 stop7h 45m
Southwest
Thu 4/307:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/15![Southwest logo]()
$336
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 March 20, 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 March 20, 2026.
This Southwest deal was found by Cheapflights users on 3/17. 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.
Wed 4/2211:55 pm
OAK
- BDL
1 stop7h 45m
Southwest
Mon 4/277:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/17![Southwest logo]()
$301
This Delta deal was found by Cheapflights users on 3/15. 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 3/315:55 am
OAK
- BOS
2 stops11h 19m
Delta
Tue 4/72:50 pm
BOS
- OAK
2 stops11h 56m
Delta
Deal found 3/15![Delta logo]()
$362
This Alaska Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 5/46:55 pm
OAK
- BOS
1 stop18h 58m
Alaska Airlines
Sat 5/95:56 pm
BOS
- OAK
1 stop19h 21m
Alaska Airlines
Deal found 3/15![Alaska Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:50 am
OAK
- BDL
1 stop7h 10m
Southwest
Fri 5/17:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/17![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 3/15. 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 5/1011:55 pm
OAK
- BDL
1 stop7h 45m
Southwest
Wed 5/136:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/15![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 3/17. 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.
Wed 4/226:10 am
OAK
- BOS
2 stops9h 25m
Southwest
Wed 5/611:40 am
BOS
- OAK
2 stops10h 10m
Southwest
Deal found 3/17![Southwest logo]()
$378
This Alaska Airlines deal was found by Cheapflights users on 3/16. 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 4/149:43 am
OAK
- BOS
2 stops11h 16m
Alaska Airlines
Tue 5/55:56 pm
BOS
- OAK
1 stop31h 27m
Alaska Airlines
Deal found 3/16![Alaska Airlines logo]()
$458
This Delta deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/74:49 pm
OAK
- BDL
2 stops14h 55m
Delta
Tue 4/142:21 pm
BDL
- OAK
2 stops12h 33m
Delta
Deal found 3/17![Delta logo]()
$469
This Southwest deal was found by Cheapflights users on 3/17. 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.
Thu 4/167:30 pm
OAK
- ALB
2 stops9h 30m
Southwest
Thu 4/237:25 pm
ALB
- OAK
1 stop8h 00m
Southwest
Deal found 3/17![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 3/17. 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.
Fri 5/2912:50 pm
OAK
- BOS
2 stops9h 00m
Southwest
Fri 6/124:45 pm
BOS
- OAK
1 stop10h 25m
Southwest
Deal found 3/17![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 3/15. 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 7/3111:55 pm
OAK
- BDL
1 stop8h 00m
Southwest
Sat 8/811:45 am
BDL
- OAK
2 stops10h 25m
Southwest
Deal found 3/15![Southwest logo]()
$396
This Expedia deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:03 pm
OAK
- ACK
2 stops11h 22m
Multiple Airlines
Wed 5/271:30 pm
ACK
- OAK
2 stops13h 29m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$1,359
This Southwest deal was found by Cheapflights users on 3/16. 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.
Thu 5/72:50 pm
OAK
- BOS
1 stop7h 00m
Southwest
Sat 5/95:15 am
BOS
- OAK
2 stops10h 10m
Southwest
Deal found 3/16![Southwest logo]()
$402
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:30 pm
OAK
- BOS
1 stop7h 35m
Southwest
Fri 5/223:45 pm
BOS
- OAK
2 stops10h 00m
Southwest
Deal found 3/19![Southwest logo]()
$402
This Southwest deal was found by Cheapflights users on 3/17. 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 8/17:40 pm
OAK
- BOS
2 stops11h 10m
Southwest
Tue 9/110:50 am
BOS
- OAK
2 stops12h 10m
Southwest
Deal found 3/17![Southwest logo]()
$432
This Southwest deal was found by Cheapflights users on 3/16. 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.
Thu 7/305:30 am
OAK
- BOS
1 stop8h 10m
Southwest
Mon 8/34:25 pm
BOS
- OAK
1 stop9h 05m
Southwest
Deal found 3/16![Southwest logo]()
$437
This Southwest deal was found by Cheapflights users on 3/17. 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.
Wed 6/177:55 pm
OAK
- ALB
2 stops9h 30m
Southwest
Wed 6/246:55 pm
ALB
- OAK
1 stop7h 35m
Southwest
Deal found 3/17![Southwest logo]()
$441
This Southwest deal was found by Cheapflights users on 3/15. 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.
Sat 6/207:40 pm
OAK
- BDL
2 stops9h 15m
Southwest
Mon 6/295:10 pm
BDL
- OAK
2 stops10h 05m
Southwest
Deal found 3/15![Southwest logo]()
$455
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:00 pm
OAK
- BOS
1 stop8h 00m
Southwest
Sat 7/116:40 am
BOS
- OAK
1 stop9h 30m
Southwest
Deal found 3/19![Southwest logo]()
$458
This Expedia deal was found by Cheapflights users on 3/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:40 pm
OAK
- MVY
2 stops11h 34m
Multiple Airlines
Sun 4/57:09 am
MVY
- OAK
2 stops13h 37m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$1,593
This Southwest deal was found by Cheapflights users on 3/15. 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 5/177:35 pm
OAK
- ALB
2 stops9h 25m
Southwest
Tue 5/192:45 pm
ALB
- OAK
2 stops10h 20m
Southwest
Deal found 3/15![Southwest logo]()
$465
This Expedia deal was found by Cheapflights users on 3/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:58 pm
OAK
- ACK
2 stops19h 52m
Multiple Airlines
Sun 5/311:30 pm
ACK
- OAK
2 stops13h 29m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$1,626
This Southwest deal was found by Cheapflights users on 3/15. 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.
Sat 6/67:40 pm
OAK
- BDL
2 stops9h 15m
Southwest
Fri 6/1212:40 pm
BDL
- OAK
2 stops10h 45m
Southwest
Deal found 3/15![Southwest logo]()
$477
This Southwest deal was found by Cheapflights users on 3/15. 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 6/57:45 pm
OAK
- ALB
2 stops9h 15m
Southwest
Sun 6/74:55 pm
ALB
- OAK
2 stops10h 55m
Southwest
Deal found 3/15![Southwest logo]()
$488
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:40 pm
OAK
- BDL
2 stops9h 25m
Southwest
Sun 6/145:35 am
BDL
- OAK
2 stops9h 40m
Southwest
Deal found 3/18![Southwest logo]()
$522
This Southwest deal was found by Cheapflights users on 3/14. 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 3/307:35 pm
OAK
- BDL
2 stops9h 30m
Southwest
Fri 4/312:20 pm
BDL
- OAK
2 stops10h 15m
Southwest
Deal found 3/14![Southwest logo]()
$526
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2410:25 am
OAK
- BDL
2 stops9h 45m
Southwest
Tue 4/286:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/19![Southwest logo]()
$540
This Southwest deal was found by Cheapflights users on 3/16. 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.
Sun 5/241:50 pm
OAK
- ALB
1 stop8h 45m
Southwest
Sun 5/3112:25 pm
ALB
- OAK
2 stops10h 10m
Southwest
Deal found 3/16![Southwest logo]()
$561
This Southwest deal was found by Cheapflights users on 3/16. 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 6/267:40 pm
OAK
- ALB
2 stops9h 20m
Southwest
Mon 6/294:30 pm
ALB
- OAK
2 stops10h 45m
Southwest
Deal found 3/16![Southwest logo]()
$607
Last-minute flights from Oakland to MassachusettsDiscover last-minute flight deals from Oakland to Massachusetts. Data last updated March 20, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Massachusetts. Data last updated March 20, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/15. 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 3/3111:55 pm
OAK
- BOS
1 stop8h 25m
Southwest
Tue 4/76:20 pm
BOS
- OAK
1 stop8h 05m
Southwest
Deal found 3/15![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:55 am
OAK
- BOS
1 stop7h 37m
Delta
Sun 4/56:15 am
BOS
- OAK
1 stop8h 36m
Delta
Deal found 3/17![Delta logo]()
$347
This CheapOair deal was found by Cheapflights users on 3/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:10 pm
OAK
- BOS
1 stop16h 17m
Alaska Airlines
Tue 4/147:15 am
BOS
- OAK
1 stop13h 31m
Alaska Airlines
Deal found 3/16![Alaska Airlines logo]()
$358
This CheapOair deal was found by Cheapflights users on 3/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:10 pm
OAK
- BOS
1 stop16h 17m
Alaska Airlines
Fri 4/106:00 am
BOS
- OAK
1 stop16h 25m
Alaska Airlines
Deal found 3/17![Alaska Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/911:55 pm
OAK
- BOS
1 stop8h 00m
Southwest
Tue 4/146:20 pm
BOS
- OAK
1 stop8h 05m
Southwest
Deal found 3/18![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 3/16. 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 4/145:55 am
OAK
- BOS
1 stop7h 39m
Delta
Tue 5/56:15 am
BOS
- OAK
1 stop8h 38m
Delta
Deal found 3/16![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:34 pm
OAK
- BOS
1 stop8h 23m
Delta
Wed 4/222:48 pm
BOS
- OAK
2 stops12h 06m
Delta
Deal found 3/18![Delta logo]()
$322
This Southwest deal was found by Cheapflights users on 3/17. 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.
Wed 4/2211:55 pm
OAK
- BDL
1 stop7h 45m
Southwest
Mon 4/277:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/17![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 3/16. 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 4/285:50 am
OAK
- BDL
1 stop7h 10m
Southwest
Fri 5/17:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/16![Southwest logo]()
$326
This CheapOair deal was found by Cheapflights users on 3/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/289:53 am
OAK
- BOS
1 stop11h 06m
Alaska Airlines
Mon 5/46:42 pm
BOS
- OAK
1 stop17h 31m
Alaska Airlines
Deal found 3/17![Alaska Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 3/17. 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.
Wed 4/295:50 am
OAK
- BOS
1 stop7h 15m
Southwest
Wed 5/134:45 pm
BOS
- OAK
1 stop8h 20m
Southwest
Deal found 3/17![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 3/15. 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 4/2911:55 pm
OAK
- BDL
1 stop7h 45m
Southwest
Thu 4/307:20 pm
BDL
- OAK
1 stop8h 05m
Southwest
Deal found 3/15![Southwest logo]()
$336
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 March 20, 2026.
Search for one-way flight options from Oakland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 20, 2026.
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:55 pm
OAK
- BDL
1 stop7h 40m
Southwest
Deal found 3/18![Southwest logo]()
$146
This Southwest deal was found by Cheapflights users on 3/16. 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.
Wed 4/297:35 pm
OAK
- BDL
2 stops9h 35m
Southwest
Deal found 3/16![Southwest logo]()
$151
This Alaska Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:03 pm
OAK
- BOS
1 stop8h 17m
Alaska Airlines
Deal found 3/19![Alaska Airlines logo]()
$154
This Southwest deal was found by Cheapflights users on 3/15. 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 6/111:55 pm
OAK
- BDL
1 stop7h 45m
Southwest
Deal found 3/15![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:35 pm
OAK
- ALB
2 stops9h 20m
Southwest
Deal found 3/19![Southwest logo]()
$158
This Delta deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:04 pm
OAK
- BOS
1 stop9h 56m
Delta
Deal found 3/17![Delta logo]()
$159
This Southwest deal was found by Cheapflights users on 3/16. 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 5/87:30 pm
OAK
- BOS
2 stops9h 35m
Southwest
Deal found 3/16![Southwest logo]()
$164
This Delta deal was found by Cheapflights users on 3/15. 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 4/145:04 pm
OAK
- BOS
1 stop9h 56m
Delta
Deal found 3/15![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 3/16. 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.
Thu 5/2810:25 am
OAK
- BDL
2 stops9h 45m
Southwest
Deal found 3/16![Southwest logo]()
$171
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:05 pm
OAK
- ALB
2 stops12h 56m
Delta
Deal found 3/19![Delta logo]()
$172
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/74:49 pm
OAK
- BOS
1 stop10h 21m
Delta
Deal found 3/18![Delta logo]()
$174
This CheapOair deal was found by Cheapflights users on 3/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/28:10 pm
OAK
- BOS
1 stop16h 17m
Alaska Airlines
Deal found 3/17![Alaska Airlines logo]()
$179
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 March 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $296 (Southwest) |
One-way from | $146 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $412 |
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 March 20, 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 - BDL
OAKBDL
Oakland
Wed 4/22
11:55 pm-10:40 am
1 stop7h 45m
Hartford Bradley Intl
Mon 4/27
7:20 pm-12:25 am
1 stop8h 05m
$301
Quickest round-trip
OaklandHartford
OAK - BDL
OAKBDL
Oakland
Tue 4/28
5:50 am-4:00 pm
1 stop7h 10m
Hartford Bradley Intl
Fri 5/1
7:20 pm-12:25 am
1 stop8h 05m
$326
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Tue 3/31
5:55 am-8:14 pm
2 stops11h 19m
Boston Logan Intl
Tue 4/7
2:50 pm-11:46 pm
2 stops11h 56m
$362
OaklandHartford
OAK - BDL
OAKBDL
Oakland
Sun 5/10
11:55 pm-10:40 am
1 stop7h 45m
Hartford Bradley Intl
Wed 5/13
6:20 pm-11:25 pm
1 stop8h 05m
$376
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Wed 4/22
6:10 am-6:35 pm
2 stops9h 25m
Boston Logan Intl
Wed 5/6
11:40 am-6:50 pm
2 stops10h 10m
$378
OaklandAlbany
OAK - ALB
OAKALB
Oakland
Thu 4/16
7:30 pm-8:00 am
2 stops9h 30m
Albany Intl
Thu 4/23
7:25 pm-12:25 am
1 stop8h 00m
$379
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Fri 5/29
12:50 pm-12:50 am
2 stops9h 00m
Boston Logan Intl
Fri 6/12
4:45 pm-12:10 am
1 stop10h 25m
$382
OaklandHartford
OAK - BDL
OAKBDL
Oakland
Fri 7/31
11:55 pm-10:55 am
1 stop8h 00m
Hartford Bradley Intl
Sat 8/8
11:45 am-7:10 pm
2 stops10h 25m
$396
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Thu 5/7
2:50 pm-12:50 am
1 stop7h 00m
Boston Logan Intl
Sat 5/9
5:15 am-12:25 pm
2 stops10h 10m
$402
OaklandBoston
OAK - BOS
OAKBOS
Oakland
Tue 5/12
1:30 pm-12:05 am
1 stop7h 35m
Boston Logan Intl
Fri 5/22
3:45 pm-10:45 pm
2 stops10h 00m
$402
Showing 1-10 of 55 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-ALB
OAK-ACK
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-ALB
OAK-ACK
What is the cheapest month to book a flight from Oakland, California to Massachusetts?
Currently, December is the cheapest month in which you can book a flight from Oakland, California to Massachusetts (average of $118). Flying from Oakland, California to Massachusetts in January is currently the most expensive (average of $189). 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 March 20, 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.
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Oakland to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oakland to Massachusetts by cabin class
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 March 20, 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 March 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$149 | Average$293 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$208 | Average$363 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$287 | Average$433 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$307 | Average$486 | FlexibilityNo cancel fee | On-time63% |