$154+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Aug 18 — Aug 251
Round-trip
1 adult, Economy
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Find cheap flights from Portland 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
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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 July 19, 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 July 19, 2026.
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1711:27 pm
PDX
- ACK
1 stop10h 36m
JetBlue
Thu 8/203:33 pm
ACK
- PDX
1 stop9h 56m
JetBlue
Deal found 7/15![JetBlue logo]()
$290
This Expedia deal was found by Cheapflights users on 7/18. 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.
Mon 8/109:56 pm
PDX
- BOS
Nonstop5h 24m
Alaska Airlines
Wed 8/195:42 pm
BOS
- PDX
Nonstop6h 08m
Alaska Airlines
Deal found 7/18![Alaska Airlines logo]()
$312
This Cheapflightsfares deal was found by Cheapflights users on 7/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1611:42 pm
PDX
- BOS
Nonstop5h 20m
JetBlue
Mon 8/249:55 am
BOS
- PDX
Nonstop6h 06m
JetBlue
Deal found 7/16![JetBlue logo]()
$314
This JetBlue deal was found by Cheapflights users on 7/17. 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.
Tue 8/42:16 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Thu 8/139:55 am
BOS
- PDX
Nonstop6h 06m
JetBlue
Deal found 7/17![JetBlue logo]()
$317
This Justfly.com deal was found by Cheapflights users on 7/17. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:15 pm
PDX
- BOS
Nonstop5h 24m
Multiple Airlines
Sat 8/298:00 am
BOS
- PDX
1 stop11h 53m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$319
This FlightHub deal was found by Cheapflights users on 7/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:15 pm
PDX
- BOS
Nonstop5h 24m
Multiple Airlines
Tue 8/258:00 am
BOS
- PDX
1 stop11h 53m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:30 pm
PDX
- BOS
2 stops10h 30m
Southwest
Tue 9/157:30 am
BOS
- PDX
2 stops10h 30m
Southwest
Deal found 7/14![Southwest logo]()
$322
This Expedia deal was found by Cheapflights users on 7/16. 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 7/312:16 pm
PDX
- BOS
Nonstop5h 24m
Multiple Airlines
Fri 8/216:17 pm
BOS
- PDX
1 stop18h 13m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$323
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:15 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Mon 8/317:32 pm
BOS
- PDX
Nonstop6h 10m
JetBlue
Deal found 7/15![JetBlue logo]()
$324
This Delta deal was found by Cheapflights users on 7/17. 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.
Sat 9/51:30 pm
PDX
- BOS
1 stop7h 28m
Delta
Wed 9/166:05 am
BOS
- PDX
1 stop8h 30m
Delta
Deal found 7/17![Delta logo]()
$327
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Mon 8/36:50 pm
PDX
- BOS
1 stop8h 08m
United Airlines
Tue 8/116:00 am
BOS
- PDX
1 stop8h 28m
United Airlines
Deal found 7/18![United Airlines logo]()
$328
This Justfly.com deal was found by Cheapflights users on 7/17. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:15 pm
PDX
- BOS
Nonstop5h 24m
Multiple Airlines
Sun 8/307:12 am
BOS
- PDX
1 stop8h 58m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$329
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 July 19, 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 July 19, 2026.
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1711:27 pm
PDX
- ACK
1 stop10h 36m
JetBlue
Thu 8/203:33 pm
ACK
- PDX
1 stop9h 56m
JetBlue
Deal found 7/15![JetBlue logo]()
$290
This Southwest deal was found by Cheapflights users on 7/17. 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 8/118:00 am
PDX
- BOS
1 stop13h 25m
Southwest
Mon 8/173:55 pm
BOS
- PDX
1 stop10h 10m
Southwest
Deal found 7/17![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 7/14. 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.
Wed 9/911:35 am
PDX
- BOS
1 stop9h 24m
Delta
Sat 9/195:55 am
BOS
- PDX
1 stop7h 54m
Delta
Deal found 7/14![Delta logo]()
$347
This American Airlines deal was found by Cheapflights users on 7/17. 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.
Tue 8/1810:59 pm
PDX
- ACK
2 stops13h 12m
American Airlines
Wed 8/2611:17 am
ACK
- PDX
2 stops10h 42m
American Airlines
Deal found 7/17![American Airlines logo]()
$401
This United Airlines deal was found by Cheapflights users on 7/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:16 am
PDX
- BDL
1 stop8h 04m
United Airlines
Tue 8/1811:44 am
BDL
- PDX
1 stop10h 09m
United Airlines
Deal found 7/14![United Airlines logo]()
$465
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:40 pm
PDX
- BOS
1 stop8h 54m
Delta
Fri 9/256:05 am
BOS
- PDX
1 stop8h 30m
Delta
Deal found 7/14![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 7/16. 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 9/2410:45 pm
PDX
- ALB
1 stop7h 45m
Southwest
Sat 9/265:20 am
ALB
- PDX
1 stop10h 10m
Southwest
Deal found 7/16![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 7/17. 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.
Wed 8/2610:50 am
PDX
- BOS
1 stop10h 01m
Delta
Sat 9/55:30 am
BOS
- PDX
1 stop7h 56m
Delta
Deal found 7/17![Delta logo]()
$348
This KAYAK deal was found by Cheapflights users on 7/14. 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 8/711:27 pm
PDX
- EWB
2 stops13h 18m
Multiple Airlines
Sat 8/157:00 am
EWB
- PDX
2 stops18h 29m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$779
This Southwest deal was found by Cheapflights users on 7/18. 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 9/2911:30 pm
PDX
- BOS
1 stop7h 25m
Southwest
Wed 10/2110:35 am
BOS
- PDX
1 stop11h 45m
Southwest
Deal found 7/18![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 7/18. 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 8/1712:35 am
PDX
- ACK
2 stops11h 06m
Delta
Wed 8/263:24 pm
ACK
- PDX
1 stop8h 49m
Delta
Deal found 7/18![Delta logo]()
$350
This Southwest deal was found by Cheapflights users on 7/15. 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 9/1711:30 pm
PDX
- ALB
1 stop8h 40m
Southwest
Mon 10/52:50 pm
ALB
- PDX
2 stops12h 20m
Southwest
Deal found 7/15![Southwest logo]()
$360
This American Airlines deal was found by Cheapflights users on 7/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1111:34 pm
PDX
- HYA
2 stops9h 38m
American Airlines
Tue 8/181:47 pm
HYA
- PDX
2 stops13h 12m
American Airlines
Deal found 7/14![American Airlines logo]()
$458
This United Airlines deal was found by Cheapflights users on 7/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2411:02 pm
PDX
- ALB
1 stop8h 22m
United Airlines
Wed 8/2611:51 am
ALB
- PDX
2 stops13h 54m
United Airlines
Deal found 7/16![United Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 7/16. 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.
Mon 8/2410:55 pm
PDX
- BDL
1 stop8h 30m
Delta
Mon 8/316:50 am
BDL
- PDX
1 stop9h 48m
Delta
Deal found 7/16![Delta logo]()
$355
This Southwest deal was found by Cheapflights users on 7/14. 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 9/167:05 am
PDX
- BDL
2 stops11h 05m
Southwest
Wed 9/233:05 pm
BDL
- PDX
2 stops11h 05m
Southwest
Deal found 7/14![Southwest logo]()
$366
This United Airlines deal was found by Cheapflights users on 7/17. 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 8/510:52 pm
PDX
- ACK
1 stop8h 23m
United Airlines
Fri 9/44:15 pm
ACK
- PDX
1 stop8h 48m
United Airlines
Deal found 7/17![United Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 7/17. 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.
Thu 9/1712:40 pm
PDX
- BOS
1 stop8h 54m
Delta
Thu 9/246:05 am
BOS
- PDX
1 stop8h 30m
Delta
Deal found 7/17![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 7/19. 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 10/3011:35 pm
PDX
- BDL
1 stop8h 35m
Southwest
Mon 11/27:25 am
BDL
- PDX
1 stop8h 20m
Southwest
Deal found 7/19![Southwest logo]()
$368
This Delta deal was found by Cheapflights users on 7/17. 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.
Thu 10/151:00 pm
PDX
- BOS
1 stop7h 58m
Delta
Sun 10/186:00 am
BOS
- PDX
1 stop8h 46m
Delta
Deal found 7/17![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 7/17. 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 10/3011:35 pm
PDX
- ALB
1 stop8h 40m
Southwest
Mon 11/26:50 pm
ALB
- PDX
1 stop8h 05m
Southwest
Deal found 7/17![Southwest logo]()
$368
This Justfly.com deal was found by Cheapflights users on 7/19. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1411:27 pm
PDX
- MVY
1 stop7h 41m
JetBlue
Sun 8/2310:58 am
MVY
- PDX
1 stop29h 03m
JetBlue
Deal found 7/19![JetBlue logo]()
$599
This Delta deal was found by Cheapflights users on 7/16. 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 10/295:49 pm
PDX
- ALB
2 stops15h 07m
Delta
Mon 11/26:20 am
ALB
- PDX
1 stop9h 50m
Delta
Deal found 7/16![Delta logo]()
$360
This American Airlines deal was found by Cheapflights users on 7/17. 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.
Tue 8/183:00 pm
PDX
- MVY
2 stops18h 00m
American Airlines
Tue 8/2512:30 pm
MVY
- PDX
2 stops14h 29m
American Airlines
Deal found 7/17![American Airlines logo]()
$598
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:35 am
PDX
- BOS
2 stops11h 05m
Southwest
Sat 10/35:25 am
BOS
- PDX
2 stops11h 35m
Southwest
Deal found 7/14![Southwest logo]()
$383
This Delta deal was found by Cheapflights users on 7/19. 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 9/111:36 am
PDX
- BDL
1 stop9h 15m
Delta
Tue 9/152:05 pm
BDL
- PDX
1 stop10h 42m
Delta
Deal found 7/19![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 7/14. 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 10/157:35 pm
PDX
- BOS
2 stops9h 35m
Southwest
Thu 10/295:50 am
BOS
- PDX
2 stops12h 00m
Southwest
Deal found 7/14![Southwest logo]()
$383
This American Airlines deal was found by Cheapflights users on 7/17. 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.
Mon 8/1711:34 pm
PDX
- MVY
2 stops14h 21m
American Airlines
Mon 8/2412:30 pm
MVY
- PDX
2 stops14h 29m
American Airlines
Deal found 7/17![American Airlines logo]()
$623
This KAYAK deal was found by Cheapflights users on 7/14. 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 8/711:27 pm
PDX
- EWB
2 stops13h 18m
Multiple Airlines
Wed 8/127:00 am
EWB
- PDX
2 stops33h 01m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$800
This Southwest deal was found by Cheapflights users on 7/17. 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 8/1911:30 pm
PDX
- BDL
1 stop9h 30m
Southwest
Tue 8/253:05 pm
BDL
- PDX
2 stops11h 05m
Southwest
Deal found 7/17![Southwest logo]()
$386
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated July 19, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated July 19, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 7/16. 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 7/312:16 pm
PDX
- BOS
Nonstop5h 24m
Multiple Airlines
Fri 8/216:17 pm
BOS
- PDX
1 stop18h 13m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Mon 8/36:50 pm
PDX
- BOS
1 stop8h 08m
United Airlines
Tue 8/116:00 am
BOS
- PDX
1 stop8h 28m
United Airlines
Deal found 7/18![United Airlines logo]()
$328
This JetBlue deal was found by Cheapflights users on 7/17. 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.
Tue 8/42:16 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Sun 8/169:55 am
BOS
- PDX
Nonstop6h 06m
JetBlue
Deal found 7/17![JetBlue logo]()
$317
This Expedia deal was found by Cheapflights users on 7/18. 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.
Mon 8/109:56 pm
PDX
- BOS
Nonstop5h 24m
Alaska Airlines
Wed 8/195:42 pm
BOS
- PDX
Nonstop6h 08m
Alaska Airlines
Deal found 7/18![Alaska Airlines logo]()
$312
This Expedia deal was found by Cheapflights users on 7/18. 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.
Mon 8/1011:27 pm
PDX
- BOS
Nonstop5h 21m
Multiple Airlines
Wed 8/195:42 pm
BOS
- PDX
Nonstop6h 08m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$322
This Cheapflightsfares deal was found by Cheapflights users on 7/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1611:42 pm
PDX
- BOS
Nonstop5h 20m
JetBlue
Mon 8/249:55 am
BOS
- PDX
Nonstop6h 06m
JetBlue
Deal found 7/16![JetBlue logo]()
$314
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1711:27 pm
PDX
- ACK
1 stop10h 36m
JetBlue
Thu 8/203:33 pm
ACK
- PDX
1 stop9h 56m
JetBlue
Deal found 7/15![JetBlue logo]()
$290
This FlightHub deal was found by Cheapflights users on 7/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:15 pm
PDX
- BOS
Nonstop5h 24m
Multiple Airlines
Tue 8/258:00 am
BOS
- PDX
1 stop11h 53m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$320
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:15 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Mon 8/317:32 pm
BOS
- PDX
Nonstop6h 10m
JetBlue
Deal found 7/15![JetBlue logo]()
$324
This JetBlue deal was found by Cheapflights users on 7/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2411:27 pm
PDX
- BOS
Nonstop5h 21m
JetBlue
Wed 8/269:55 am
BOS
- PDX
Nonstop6h 06m
JetBlue
Deal found 7/14![JetBlue logo]()
$327
This Justfly.com deal was found by Cheapflights users on 7/17. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:15 pm
PDX
- BOS
Nonstop5h 24m
Multiple Airlines
Sat 8/298:00 am
BOS
- PDX
1 stop11h 53m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$319
This Justfly.com deal was found by Cheapflights users on 7/17. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:15 pm
PDX
- BOS
Nonstop5h 24m
Multiple Airlines
Sun 8/307:12 am
BOS
- PDX
1 stop8h 58m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$329
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 July 19, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 19, 2026.
This Southwest deal was found by Cheapflights users on 7/18. 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 9/811:30 pm
PDX
- BOS
2 stops10h 10m
Southwest
Deal found 7/18![Southwest logo]()
$154
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:15 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Deal found 7/14![JetBlue logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 7/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:16 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Deal found 7/14![JetBlue logo]()
$162
This JetBlue deal was found by Cheapflights users on 7/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:27 pm
PDX
- BOS
Nonstop5h 21m
JetBlue
Deal found 7/14![JetBlue logo]()
$164
This Super.com deal was found by Cheapflights users on 7/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/52:16 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Deal found 7/15![JetBlue logo]()
$166
This Cheapflightsfares deal was found by Cheapflights users on 7/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:15 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Deal found 7/16![JetBlue logo]()
$167
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1011:27 pm
PDX
- BOS
Nonstop5h 21m
JetBlue
Deal found 7/15![JetBlue logo]()
$169
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:16 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Deal found 7/15![JetBlue logo]()
$172
This United Airlines deal was found by Cheapflights users on 7/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:02 am
PDX
- BOS
1 stop9h 17m
United Airlines
Deal found 7/14![United Airlines logo]()
$174
This Super.com deal was found by Cheapflights users on 7/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1611:42 pm
PDX
- BOS
Nonstop5h 20m
JetBlue
Deal found 7/16![JetBlue logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 7/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/12:16 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Deal found 7/16![JetBlue logo]()
$177
This Delta deal was found by Cheapflights users on 7/15. 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 8/2510:55 pm
PDX
- BDL
1 stop8h 30m
Delta
Deal found 7/15![Delta logo]()
$178
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 July 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $290 (JetBlue) |
One-way from | $154 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $415 |
Good round-trip deal | $337 or less |
Good one-way deal | $178 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 July 19, 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
PortlandNantucket
PDX - ACK
PDXACK
Portland
Mon 8/17
11:27 pm-1:03 pm
1 stop10h 36m
Nantucket Memorial
Thu 8/20
3:33 pm-10:29 pm
1 stop9h 56m
$290
PortlandBoston
PDX - BOS
PDXBOS
Portland
Tue 8/11
8:00 am-12:25 am
1 stop13h 25m
Boston Logan Intl
Mon 8/17
3:55 pm-11:05 pm
1 stop10h 10m
$337
PortlandBoston
PDX - BOS
PDXBOS
Portland
Wed 9/9
11:35 am-11:59 pm
1 stop9h 24m
Boston Logan Intl
Sat 9/19
5:55 am-10:49 am
1 stop7h 54m
$347
PortlandBoston
PDX - BOS
PDXBOS
Portland
Tue 9/15
12:40 pm-12:34 am
1 stop8h 54m
Boston Logan Intl
Fri 9/25
6:05 am-11:35 am
1 stop8h 30m
$347
PortlandBoston
PDX - BOS
PDXBOS
Portland
Wed 8/26
10:50 am-11:51 pm
1 stop10h 01m
Boston Logan Intl
Sat 9/5
5:30 am-10:26 am
1 stop7h 56m
$348
PortlandNantucket
PDX - ACK
PDXACK
Portland
Mon 8/17
12:35 am-2:41 pm
2 stops11h 06m
Nantucket Memorial
Wed 8/26
3:24 pm-9:13 pm
1 stop8h 49m
$350
PortlandAlbany
PDX - ALB
PDXALB
Portland
Thu 9/24
10:45 pm-9:30 am
1 stop7h 45m
Albany Intl
Sat 9/26
5:20 am-12:30 pm
1 stop10h 10m
$355
PortlandHartford
PDX - BDL
PDXBDL
Portland
Mon 8/24
10:55 pm-10:25 am
1 stop8h 30m
Hartford Bradley Intl
Mon 8/31
6:50 am-1:38 pm
1 stop9h 48m
$355
PortlandBoston
PDX - BOS
PDXBOS
Portland
Tue 9/29
11:30 pm-9:55 am
1 stop7h 25m
Boston Logan Intl
Wed 10/21
10:35 am-7:20 pm
1 stop11h 45m
$357
PortlandBoston
PDX - BOS
PDXBOS
Portland
Thu 9/17
12:40 pm-12:34 am
1 stop8h 54m
Boston Logan Intl
Thu 9/24
6:05 am-11:35 am
1 stop8h 30m
$357
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-ACK
PDX-BOS
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-ACK
PDX-BOS
PDX-BDL
PDX-ALB
What is the cheapest month to book a flight from Portland to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $324). Flying from Portland to Massachusetts in December is currently the most expensive (average of $502). 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 July 19, 2026.
It’s typically best to fly out from Portland to Massachusetts at noon. Doing so could potentially save you 28% 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 July 19, 2026.
The most flights from PDX to USMA are scheduled on a Friday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Portland to Massachusetts?
How far ahead should I book a flight from Portland to Massachusetts?
Booking 90 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Massachusetts. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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 July 19, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Delta, andUnited 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.
Overall
7.9
Boarding
8.1
Crew
8.5
Comfort
7.8
Food
7.0
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Boarding
8.1
Crew
8.5
Comfort
7.8
Food
7.0
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Boarding
8.1
Crew
8.5
Comfort
7.8
Food
7.0
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Boarding
8.1
Crew
8.5
Comfort
7.8
Food
7.0
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Boarding
8.1
Crew
8.5
Comfort
7.8
Food
7.0
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Boarding
8.1
Crew
8.5
Comfort
7.8
Food
7.0
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
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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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 July 19, 2026.
Popular flight searches
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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 July 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$411 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$118 | Average$278 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$178 | Average$296 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$184 | Average$389 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$205 | Average$368 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$236 | Average$372 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$278 | Average$498 | FlexibilityNo cancel fee | On-time75% |