$125+ Cheap flights from Portland (PDX) 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Apr 21 — Apr 281
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Massachusetts with Cheapflights
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Cheapest flights from Portland to MassachusettsExplore the most affordable flight options available from Portland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 22, 2026.
Explore the most affordable flight options available from Portland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 22, 2026.
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/512:30 am
PDX
- BOS
1 stop7h 16m
Delta
Sat 5/96:10 am
BOS
- PDX
1 stop9h 16m
Delta
Deal found 3/20![Delta logo]()
$239
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.
Mon 4/206:05 pm
PDX
- BOS
1 stop9h 50m
Delta
Wed 4/297:37 am
BOS
- PDX
1 stop8h 15m
Delta
Deal found 3/18![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/287:25 pm
PDX
- BOS
2 stops9h 50m
Southwest
Mon 5/46:55 pm
BOS
- PDX
1 stop8h 15m
Southwest
Deal found 3/20![Southwest logo]()
$244
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 5/97:40 pm
PDX
- BOS
2 stops11h 15m
Southwest
Tue 5/1210:45 am
BOS
- PDX
2 stops13h 00m
Southwest
Deal found 3/18![Southwest logo]()
$249
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/910:56 pm
PDX
- BOS
1 stop7h 29m
United Airlines
Thu 4/306:00 am
BOS
- PDX
1 stop9h 35m
United Airlines
Deal found 3/18![United Airlines logo]()
$259
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/1311:55 pm
PDX
- BOS
2 stops9h 20m
Southwest
Wed 4/152:25 pm
BOS
- PDX
1 stop11h 45m
Southwest
Deal found 3/21![Southwest logo]()
$260
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.
Tue 4/77:17 pm
PDX
- BOS
1 stop7h 53m
Delta
Tue 4/146:15 am
BOS
- PDX
1 stop9h 02m
Delta
Deal found 3/19![Delta logo]()
$263
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 4/911:55 pm
PDX
- BOS
1 stop8h 00m
Southwest
Wed 4/152:25 pm
BOS
- PDX
1 stop11h 45m
Southwest
Deal found 3/17![Southwest logo]()
$264
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/810:15 pm
PDX
- BOS
1 stop7h 56m
United Airlines
Sun 5/106:00 am
BOS
- PDX
1 stop9h 35m
United Airlines
Deal found 3/20![United Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:30 pm
PDX
- BOS
1 stop7h 17m
American Airlines
Tue 8/256:00 am
BOS
- PDX
1 stop8h 32m
American Airlines
Deal found 3/22![American Airlines logo]()
$273
This United Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:55 pm
PDX
- BOS
1 stop7h 30m
United Airlines
Mon 5/116:39 pm
BOS
- PDX
1 stop8h 16m
United Airlines
Deal found 3/21![United Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 8/1712:40 am
PDX
- ACK
2 stops9h 47m
Delta
Tue 8/252:10 pm
ACK
- PDX
1 stop10h 25m
Delta
Deal found 3/22![Delta logo]()
$318
Best flights from Portland to MassachusettsDiscover carefully curated flight deals from Portland to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 22, 2026.
Discover carefully curated flight deals from Portland to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 22, 2026.
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 6/97:14 pm
PDX
- BOS
1 stop7h 55m
Delta
Tue 6/166:00 am
BOS
- PDX
1 stop8h 43m
Delta
Deal found 3/17![Delta logo]()
$239
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:40 pm
PDX
- BOS
1 stop7h 59m
United Airlines
Thu 5/284:57 pm
BOS
- PDX
1 stop8h 58m
United Airlines
Deal found 3/22![United Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/2011:55 pm
PDX
- BOS
1 stop8h 05m
Southwest
Mon 4/273:45 pm
BOS
- PDX
2 stops12h 10m
Southwest
Deal found 3/21![Southwest logo]()
$244
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:59 pm
PDX
- ACK
2 stops13h 35m
American Airlines
Wed 8/265:13 pm
ACK
- PDX
1 stop10h 45m
American Airlines
Deal found 3/18![American Airlines logo]()
$318
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.
Wed 8/265:30 pm
PDX
- BOS
1 stop11h 01m
Alaska Airlines
Thu 9/310:30 am
BOS
- PDX
Nonstop6h 19m
Alaska Airlines
Deal found 3/19![Alaska Airlines logo]()
$342
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.
Mon 4/2011:55 pm
PDX
- BOS
2 stops9h 20m
Southwest
Wed 4/292:25 pm
BOS
- PDX
2 stops11h 35m
Southwest
Deal found 3/19![Southwest logo]()
$249
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:18 pm
PDX
- ACK
1 stop10h 43m
JetBlue
Wed 8/193:43 pm
ACK
- PDX
1 stop9h 40m
JetBlue
Deal found 3/17![JetBlue logo]()
$539
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:30 pm
PDX
- BOS
1 stop7h 29m
United Airlines
Sat 4/112:37 pm
BOS
- PDX
1 stop9h 05m
United Airlines
Deal found 3/19![United Airlines logo]()
$306
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/277:25 pm
PDX
- BOS
2 stops9h 40m
Southwest
Thu 5/286:55 pm
BOS
- PDX
1 stop8h 15m
Southwest
Deal found 3/22![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 8/1712:40 am
PDX
- ACK
2 stops9h 47m
Delta
Tue 8/252:10 pm
ACK
- PDX
1 stop10h 25m
Delta
Deal found 3/22![Delta logo]()
$318
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 8/1712:40 am
PDX
- ACK
2 stops9h 47m
Delta
Wed 8/262:10 pm
ACK
- PDX
1 stop10h 25m
Delta
Deal found 3/22![Delta logo]()
$346
This American Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1811:47 pm
PDX
- BOS
1 stop8h 45m
American Airlines
Thu 5/216:00 am
BOS
- PDX
1 stop8h 34m
American Airlines
Deal found 3/22![American Airlines logo]()
$388
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:05 pm
PDX
- BOS
2 stops11h 06m
United Airlines
Sat 4/255:30 am
BOS
- PDX
1 stop9h 55m
United Airlines
Deal found 3/18![United Airlines logo]()
$364
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 5/88:35 am
PDX
- BOS
2 stops10h 45m
Southwest
Tue 5/1210:45 am
BOS
- PDX
2 stops13h 00m
Southwest
Deal found 3/19![Southwest logo]()
$339
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:45 pm
PDX
- BOS
2 stops14h 01m
United Airlines
Mon 5/116:39 pm
BOS
- PDX
1 stop8h 16m
United Airlines
Deal found 3/19![United Airlines logo]()
$374
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:34 pm
PDX
- ALB
1 stop7h 49m
American Airlines
Tue 5/266:15 am
ALB
- PDX
1 stop8h 19m
American Airlines
Deal found 3/17![American Airlines logo]()
$416
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 4/29:30 pm
PDX
- HYA
1 stop10h 32m
Multiple Airlines
Mon 4/612:07 pm
HYA
- PDX
1 stop10h 41m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$955
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2711:05 am
PDX
- BDL
2 stops9h 54m
United Airlines
Tue 6/212:12 pm
BDL
- PDX
1 stop9h 35m
United Airlines
Deal found 3/17![United Airlines logo]()
$380
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.
Wed 4/297:25 pm
PDX
- BDL
2 stops9h 45m
Southwest
Tue 5/512:25 pm
BDL
- PDX
2 stops11h 20m
Southwest
Deal found 3/19![Southwest logo]()
$385
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 8/1710:05 pm
PDX
- ACK
1 stop12h 22m
Delta
Tue 8/252:10 pm
ACK
- PDX
1 stop10h 25m
Delta
Deal found 3/21![Delta logo]()
$442
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/2811:55 pm
PDX
- BDL
1 stop7h 45m
Southwest
Mon 5/47:20 pm
BDL
- PDX
1 stop7h 50m
Southwest
Deal found 3/20![Southwest logo]()
$387
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:14 pm
PDX
- ALB
2 stops11h 59m
United Airlines
Sat 4/256:05 am
ALB
- PDX
1 stop8h 39m
United Airlines
Deal found 3/20![United Airlines logo]()
$392
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 4/227:25 pm
PDX
- BDL
2 stops9h 45m
Southwest
Mon 4/274:40 pm
BDL
- PDX
2 stops10h 30m
Southwest
Deal found 3/17![Southwest logo]()
$409
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/411:55 pm
PDX
- ALB
2 stops9h 10m
Southwest
Mon 5/112:55 pm
ALB
- PDX
2 stops13h 00m
Southwest
Deal found 3/20![Southwest logo]()
$409
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:57 pm
PDX
- BDL
2 stops11h 40m
United Airlines
Wed 9/2310:00 am
BDL
- PDX
1 stop8h 30m
United Airlines
Deal found 3/18![United Airlines logo]()
$462
This American Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/69:52 pm
PDX
- HYA
2 stops12h 16m
American Airlines
Mon 8/102:41 pm
HYA
- PDX
2 stops11h 41m
American Airlines
Deal found 3/22![American Airlines logo]()
$667
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1410:50 am
PDX
- BDL
2 stops10h 09m
United Airlines
Fri 4/176:49 pm
BDL
- PDX
1 stop8h 10m
United Airlines
Deal found 3/22![United Airlines logo]()
$467
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 6/49:20 pm
PDX
- ALB
1 stop8h 05m
Southwest
Mon 6/87:15 pm
ALB
- PDX
1 stop7h 40m
Southwest
Deal found 3/17![Southwest logo]()
$428
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2211:18 pm
PDX
- PVC
1 stop8h 02m
JetBlue
Wed 8/267:00 am
PVC
- PDX
1 stop9h 04m
JetBlue
Deal found 3/17![JetBlue logo]()
$836
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 6/35:40 am
PDX
- ALB
2 stops10h 05m
Southwest
Sun 6/74:55 pm
ALB
- PDX
1 stop9h 00m
Southwest
Deal found 3/17![Southwest logo]()
$431
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated March 22, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated March 22, 2026 and is based on user searches.
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 4/611:15 pm
PDX
- BOS
1 stop7h 01m
Delta
Tue 4/146:15 am
BOS
- PDX
1 stop9h 02m
Delta
Deal found 3/19![Delta logo]()
$278
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.
Tue 4/77:17 pm
PDX
- BOS
1 stop7h 53m
Delta
Tue 4/146:15 am
BOS
- PDX
1 stop9h 02m
Delta
Deal found 3/19![Delta logo]()
$263
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:59 pm
PDX
- BOS
1 stop9h 47m
United Airlines
Mon 4/136:48 pm
BOS
- PDX
1 stop8h 11m
United Airlines
Deal found 3/19![United Airlines logo]()
$273
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/910:56 pm
PDX
- BOS
1 stop7h 29m
United Airlines
Thu 4/306:00 am
BOS
- PDX
1 stop9h 35m
United Airlines
Deal found 3/18![United Airlines logo]()
$259
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 4/911:55 pm
PDX
- BOS
1 stop8h 00m
Southwest
Wed 4/152:25 pm
BOS
- PDX
1 stop11h 45m
Southwest
Deal found 3/17![Southwest logo]()
$264
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/1311:55 pm
PDX
- BOS
2 stops9h 20m
Southwest
Wed 4/152:25 pm
BOS
- PDX
1 stop11h 45m
Southwest
Deal found 3/21![Southwest logo]()
$260
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.
Mon 4/206:05 pm
PDX
- BOS
1 stop9h 50m
Delta
Wed 4/297:37 am
BOS
- PDX
1 stop8h 15m
Delta
Deal found 3/18![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/225:40 am
PDX
- BOS
1 stop9h 55m
Southwest
Tue 4/286:20 pm
BOS
- PDX
1 stop7h 50m
Southwest
Deal found 3/22![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/2811:55 pm
PDX
- BOS
1 stop8h 05m
Southwest
Mon 5/46:55 pm
BOS
- PDX
1 stop8h 15m
Southwest
Deal found 3/20![Southwest logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:38 pm
PDX
- BDL
2 stops23h 11m
Multiple Airlines
Wed 5/66:34 pm
BDL
- PDX
1 stop27h 22m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$364
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2911:59 pm
PDX
- BDL
1 stop6h 56m
United Airlines
Tue 5/512:40 pm
BDL
- PDX
1 stop9h 05m
United Airlines
Deal found 3/19![United Airlines logo]()
$375
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.
Wed 4/2911:55 pm
PDX
- BDL
1 stop7h 45m
Southwest
Tue 5/59:20 am
BDL
- PDX
2 stops12h 10m
Southwest
Deal found 3/19![Southwest logo]()
$380
One-way flights from Portland to MassachusettsSearch for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 22, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 22, 2026.
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/187:40 pm
PDX
- BOS
2 stops9h 50m
Southwest
Deal found 3/20![Southwest logo]()
$125
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1610:56 pm
PDX
- BOS
1 stop7h 29m
United Airlines
Deal found 3/18![United Airlines logo]()
$130
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:59 pm
PDX
- BOS
1 stop8h 02m
United Airlines
Deal found 3/18![United Airlines logo]()
$144
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.
Tue 4/77:25 pm
PDX
- BOS
2 stops9h 50m
Southwest
Deal found 3/18![Southwest logo]()
$149
This American Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1610:40 pm
PDX
- BOS
1 stop8h 17m
American Airlines
Deal found 3/20![American Airlines logo]()
$154
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/1410:40 pm
PDX
- BOS
1 stop7h 59m
United Airlines
Deal found 3/18![United Airlines logo]()
$155
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:05 am
PDX
- BOS
1 stop8h 01m
United Airlines
Deal found 3/22![United Airlines logo]()
$158
This KAYAK deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 6/162:20 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Deal found 3/20![JetBlue logo]()
$159
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/19:44 pm
PDX
- BOS
1 stop10h 52m
American Airlines
Deal found 3/18![American Airlines logo]()
$160
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3111:30 pm
PDX
- BOS
1 stop7h 50m
United Airlines
Deal found 3/18![United Airlines logo]()
$161
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 8/1712:40 am
PDX
- ACK
2 stops9h 47m
Delta
Deal found 3/21![Delta logo]()
$162
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2710:40 pm
PDX
- BOS
1 stop7h 59m
United Airlines
Deal found 3/20![United Airlines logo]()
$162
Find flight deals from Portland to Massachusetts
Keep the following information in mind while searching for Portland to Massachusetts flight deals. Data was last updated March 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $239 (Delta) |
One-way from | $125 (Southwest) |
Popular in | December |
Cheapest in | May |
Average price | $404 |
Good round-trip deal | $313 or less |
Good one-way deal | $193 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland 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 22, 2026.
Use the filters below to find and compare flights from Portland to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandBoston
PDX - BOS
PDXBOS
Portland
Tue 6/9
7:14 pm-6:09 am
1 stop7h 55m
Boston Logan Intl
Tue 6/16
6:00 am-11:43 am
1 stop8h 43m
$239
PortlandBoston
PDX - BOS
PDXBOS
Portland
Wed 5/27
10:40 pm-9:39 am
1 stop7h 59m
Boston Logan Intl
Thu 5/28
4:57 pm-10:55 pm
1 stop8h 58m
$239
PortlandBoston
PDX - BOS
PDXBOS
Portland
Mon 4/20
11:55 pm-11:00 am
1 stop8h 05m
Boston Logan Intl
Mon 4/27
3:45 pm-12:55 am
2 stops12h 10m
$244
PortlandBoston
PDX - BOS
PDXBOS
Portland
Mon 4/20
11:55 pm-12:15 pm
2 stops9h 20m
Boston Logan Intl
Wed 4/29
2:25 pm-11:00 pm
2 stops11h 35m
$249
PortlandBoston
PDX - BOS
PDXBOS
Portland
Wed 5/27
7:25 pm-8:05 am
2 stops9h 40m
Boston Logan Intl
Thu 5/28
6:55 pm-12:10 am
1 stop8h 15m
$285
PortlandBoston
PDX - BOS
PDXBOS
Portland
Thu 4/9
2:30 pm-12:59 am
1 stop7h 29m
Boston Logan Intl
Sat 4/11
2:37 pm-8:42 pm
1 stop9h 05m
$306
PortlandNantucket
PDX - ACK
PDXACK
Portland
Tue 8/18
11:59 pm-4:34 pm
2 stops13h 35m
Nantucket Memorial
Wed 8/26
5:13 pm-12:58 am
1 stop10h 45m
$318
PortlandNantucket
PDX - ACK
PDXACK
Portland
Mon 8/17
12:40 am-1:27 pm
2 stops9h 47m
Nantucket Memorial
Tue 8/25
2:10 pm-9:35 pm
1 stop10h 25m
$318
PortlandBoston
PDX - BOS
PDXBOS
Portland
Fri 5/8
8:35 am-10:20 pm
2 stops10h 45m
Boston Logan Intl
Tue 5/12
10:45 am-8:45 pm
2 stops13h 00m
$339
PortlandBoston
PDX - BOS
PDXBOS
Portland
Wed 8/26
5:30 pm-7:31 am
1 stop11h 01m
Boston Logan Intl
Thu 9/3
10:30 am-1:49 pm
Nonstop6h 19m
$342
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Portland to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Portland with our price prediction graph.
PDX-BOS
PDX-ACK
PDX-BDL
PDX-ALB
PDX-EWB
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 Portland to Massachusetts
PDX-USMA
PDX-BOS
PDX-ACK
PDX-BDL
PDX-ALB
What is the cheapest month to book a flight from Portland to Massachusetts?
Currently, June is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $108). Flying from Portland to Massachusetts in October is currently the most expensive (average of $197). 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.
What is the cheapest time of day to fly from PDX to MA?
Find hourly flight availability from Portland to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 22, 2026.
It’s typically best to fly out from Portland to Massachusetts at noon. Doing so could potentially save you 46% on the flight price compared to flying in the morning, which is usually more expensive.
Weekly flight availability from Portland to Massachusetts
Explore weekly flight availability from Portland to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 22, 2026.
The most flights from PDX to USMA are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
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 22, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Delta, andHawaiian Airlines from Portland to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Related info for your journey
Find useful and relevant information for your journey from Portland to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Portland to Massachusetts
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Complete your trip
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Search flights from Portland to Massachusetts by cabin class
Find flights from Portland to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Massachusetts flights
Browse other Portland and Massachusetts flight options. Last updated on March 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Portland to Massachusetts flights
Consider these flights traveling from Portland to Massachusetts.
Top 7 airlines flying from Portland to Massachusetts
Discover the top 7 airlines that operate flights from Portland 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$277 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$108 | Average$319 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$108 | Average$293 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$277 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$184 | Average$386 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$236 | Average$380 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$248 | Average$471 | FlexibilityNo cancel fee | On-time75% |