$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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
May 3 — May 101
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 April 3, 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 April 3, 2026.
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2212:20 pm
PDX
- BOS
1 stop9h 20m
Delta
Sun 5/245:51 am
BOS
- PDX
1 stop8h 02m
Delta
Deal found 4/2![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 4/2112:30 am
PDX
- BOS
1 stop7h 16m
Delta
Fri 5/111:00 am
BOS
- PDX
1 stop10h 52m
Delta
Deal found 4/1![Delta logo]()
$218
This American Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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.
Sat 5/2310:59 pm
PDX
- BOS
1 stop8h 30m
American Airlines
Sat 5/306:00 am
BOS
- PDX
1 stop8h 34m
American Airlines
Deal found 4/2![American Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 9/710:55 pm
PDX
- BOS
1 stop7h 05m
Delta
Tue 10/65:30 am
BOS
- PDX
1 stop8h 35m
Delta
Deal found 4/1![Delta logo]()
$223
This American Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/2010:23 pm
PDX
- BOS
1 stop9h 29m
American Airlines
Tue 4/284:21 pm
BOS
- PDX
1 stop9h 28m
American Airlines
Deal found 4/2![American Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Sat 5/911:48 am
PDX
- BOS
1 stop9h 36m
American Airlines
Wed 5/134:32 pm
BOS
- PDX
1 stop9h 15m
American Airlines
Deal found 3/31![American Airlines logo]()
$229
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/127:00 am
PDX
- BOS
1 stop11h 00m
American Airlines
Thu 5/286:00 am
BOS
- PDX
1 stop8h 34m
American Airlines
Deal found 3/31![American Airlines logo]()
$234
This American Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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.
Fri 5/1512:59 am
PDX
- BOS
1 stop9h 12m
American Airlines
Sat 5/235:04 pm
BOS
- PDX
1 stop9h 19m
American Airlines
Deal found 4/1![American Airlines logo]()
$235
This United Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/302:41 pm
PDX
- BOS
1 stop7h 18m
United Airlines
Sat 5/26:00 am
BOS
- PDX
1 stop9h 34m
United Airlines
Deal found 4/2![United Airlines logo]()
$237
This SmartFares deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:46 pm
PDX
- BOS
Nonstop5h 34m
Alaska Airlines
Sat 5/306:00 am
BOS
- PDX
Nonstop6h 11m
Alaska Airlines
Deal found 4/2![Alaska Airlines logo]()
$238
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2812:30 am
PDX
- BOS
1 stop7h 16m
Delta
Mon 5/46:10 am
BOS
- PDX
1 stop12h 28m
Delta
Deal found 3/31![Delta logo]()
$239
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 3/30![Delta logo]()
$288
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 April 3, 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 April 3, 2026.
This United Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/510:15 pm
PDX
- BOS
1 stop7h 56m
United Airlines
Tue 5/126:00 am
BOS
- PDX
1 stop9h 35m
United Airlines
Deal found 3/31![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 3/30![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 5/197:25 pm
PDX
- BOS
2 stops9h 50m
Southwest
Thu 6/44:45 pm
BOS
- PDX
1 stop10h 10m
Southwest
Deal found 3/29![Southwest logo]()
$308
This Alaska Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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.
Sat 5/169:46 pm
PDX
- BOS
Nonstop5h 34m
Alaska Airlines
Sat 5/236:40 pm
BOS
- PDX
1 stop18h 06m
Alaska Airlines
Deal found 4/1![Alaska Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 8/189:52 pm
PDX
- MVY
2 stops15h 33m
American Airlines
Tue 8/2510:42 am
MVY
- PDX
2 stops13h 10m
American Airlines
Deal found 3/29![American Airlines logo]()
$419
This KAYAK deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2511:29 pm
PDX
- ACK
1 stop10h 34m
JetBlue
Sun 6/283:43 pm
ACK
- PDX
1 stop9h 51m
JetBlue
Deal found 3/31![JetBlue logo]()
$579
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 5/110:55 am
PDX
- BOS
1 stop10h 55m
Southwest
Mon 5/44:45 pm
BOS
- PDX
2 stops10h 25m
Southwest
Deal found 3/29![Southwest logo]()
$316
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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
- BOS
1 stop8h 02m
United Airlines
Wed 5/63:00 pm
BOS
- PDX
1 stop10h 35m
United Airlines
Deal found 3/29![United Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 5/110:55 am
PDX
- BOS
2 stops9h 15m
Southwest
Fri 5/811:35 am
BOS
- PDX
2 stops11h 35m
Southwest
Deal found 4/2![Southwest logo]()
$348
This United Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 5/610:55 pm
PDX
- BOS
2 stops10h 56m
United Airlines
Wed 5/133:00 pm
BOS
- PDX
1 stop10h 35m
United Airlines
Deal found 4/2![United Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 6/306:15 am
PDX
- BOS
1 stop9h 55m
Delta
Wed 7/85:55 am
BOS
- PDX
1 stop7h 46m
Delta
Deal found 4/2![Delta logo]()
$388
This United Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 5/111:55 pm
PDX
- BOS
2 stops10h 56m
United Airlines
Sun 5/36:00 am
BOS
- PDX
1 stop11h 06m
United Airlines
Deal found 4/2![United Airlines logo]()
$352
This Alaska Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Sat 5/27:30 am
PDX
- BOS
Nonstop5h 33m
Alaska Airlines
Sun 5/37:00 am
BOS
- PDX
1 stop8h 52m
Alaska Airlines
Deal found 3/31![Alaska Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 5/2011:12 pm
PDX
- BDL
1 stop6h 30m
Delta
Sun 5/246:00 am
BDL
- PDX
1 stop7h 53m
Delta
Deal found 4/1![Delta logo]()
$416
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/285:40 am
PDX
- ALB
1 stop7h 00m
Southwest
Tue 5/512:20 pm
ALB
- PDX
2 stops11h 40m
Southwest
Deal found 3/30![Southwest logo]()
$380
This Alaska Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:30 am
PDX
- BOS
Nonstop5h 33m
Alaska Airlines
Wed 5/65:05 pm
BOS
- PDX
Nonstop6h 20m
Alaska Airlines
Deal found 3/31![Alaska Airlines logo]()
$447
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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
PDX
- BDL
1 stop7h 45m
Southwest
Mon 4/277:20 pm
BDL
- PDX
1 stop7h 50m
Southwest
Deal found 4/2![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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
Mon 8/2410:00 am
ACK
- PDX
2 stops14h 46m
Delta
Deal found 4/2![Delta logo]()
$431
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 5/511:55 pm
PDX
- BDL
1 stop7h 00m
United Airlines
Thu 5/76:00 am
BDL
- PDX
1 stop8h 37m
United Airlines
Deal found 3/29![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 8/2012:40 am
PDX
- BDL
1 stop7h 08m
Delta
Fri 8/286:30 pm
BDL
- PDX
1 stop8h 04m
Delta
Deal found 3/29![Delta logo]()
$457
This Expedia deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/179:30 pm
PDX
- HYA
1 stop10h 32m
Multiple Airlines
Tue 4/216:24 am
HYA
- PDX
2 stops17h 26m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$1,261
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/288:35 am
PDX
- BDL
2 stops11h 35m
Southwest
Mon 6/14:40 pm
BDL
- PDX
2 stops10h 30m
Southwest
Deal found 3/31![Southwest logo]()
$438
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 8/2710:55 pm
PDX
- BDL
1 stop6h 47m
Delta
Sun 8/305:48 am
BDL
- PDX
1 stop7h 56m
Delta
Deal found 3/29![Delta logo]()
$457
This United Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 9/2111:15 pm
PDX
- BDL
1 stop7h 44m
United Airlines
Sat 9/266:15 am
BDL
- PDX
1 stop8h 20m
United Airlines
Deal found 4/2![United Airlines logo]()
$457
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/15:10 am
PDX
- BDL
2 stops15h 00m
Southwest
Mon 5/44:40 pm
BDL
- PDX
2 stops10h 30m
Southwest
Deal found 3/31![Southwest logo]()
$444
This American Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 8/55:42 pm
PDX
- MVY
2 stops15h 14m
American Airlines
Mon 8/1011:59 am
MVY
- PDX
2 stops14h 23m
American Airlines
Deal found 3/29![American Airlines logo]()
$733
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 7/2910:40 pm
PDX
- BDL
1 stop8h 16m
United Airlines
Wed 8/125:04 pm
BDL
- PDX
1 stop9h 05m
United Airlines
Deal found 3/29![United Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 8/2710:55 pm
PDX
- ALB
1 stop7h 06m
Delta
Sun 8/306:00 am
ALB
- PDX
1 stop7h 44m
Delta
Deal found 3/31![Delta logo]()
$457
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 9/311:30 pm
PDX
- ALB
1 stop8h 40m
Southwest
Mon 9/77:00 am
ALB
- PDX
1 stop8h 50m
Southwest
Deal found 4/2![Southwest logo]()
$457
This United Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2411:59 pm
PDX
- BDL
1 stop7h 04m
United Airlines
Mon 4/275:10 pm
BDL
- PDX
1 stop9h 49m
United Airlines
Deal found 3/31![United Airlines logo]()
$458
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated April 3, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated April 3, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/2010:23 pm
PDX
- BOS
1 stop9h 29m
American Airlines
Tue 4/284:21 pm
BOS
- PDX
1 stop9h 28m
American Airlines
Deal found 4/2![American Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 4/2112:30 am
PDX
- BOS
1 stop7h 16m
Delta
Fri 5/111:00 am
BOS
- PDX
1 stop10h 52m
Delta
Deal found 4/1![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2812:30 am
PDX
- BOS
1 stop7h 16m
Delta
Wed 5/610:20 am
BOS
- PDX
1 stop8h 47m
Delta
Deal found 3/31![Delta logo]()
$239
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2910:23 pm
PDX
- BDL
1 stop7h 47m
American Airlines
Tue 5/54:09 pm
BDL
- PDX
1 stop10h 48m
American Airlines
Deal found 3/31![American Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/302:41 pm
PDX
- BOS
1 stop7h 18m
United Airlines
Sat 5/26:00 am
BOS
- PDX
1 stop9h 34m
United Airlines
Deal found 4/2![United Airlines logo]()
$237
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Sat 5/911:48 am
PDX
- BOS
1 stop9h 36m
American Airlines
Wed 5/134:32 pm
BOS
- PDX
1 stop9h 15m
American Airlines
Deal found 3/31![American Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 5/911:55 pm
PDX
- BOS
1 stop10h 00m
Southwest
Tue 5/1210:45 am
BOS
- PDX
2 stops13h 00m
Southwest
Deal found 4/2![Southwest logo]()
$244
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/127:00 am
PDX
- BOS
1 stop11h 00m
American Airlines
Thu 5/286:00 am
BOS
- PDX
1 stop8h 34m
American Airlines
Deal found 3/31![American Airlines logo]()
$234
This American Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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.
Fri 5/1512:59 am
PDX
- BOS
1 stop9h 12m
American Airlines
Sat 5/235:04 pm
BOS
- PDX
1 stop9h 19m
American Airlines
Deal found 4/1![American Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2212:20 pm
PDX
- BOS
1 stop9h 20m
Delta
Sun 5/245:51 am
BOS
- PDX
1 stop8h 02m
Delta
Deal found 4/2![Delta logo]()
$217
This American Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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.
Sat 5/2310:59 pm
PDX
- BOS
1 stop8h 30m
American Airlines
Sat 5/306:00 am
BOS
- PDX
1 stop8h 34m
American Airlines
Deal found 4/2![American Airlines logo]()
$219
This SmartFares deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:46 pm
PDX
- BOS
Nonstop5h 34m
Alaska Airlines
Sat 5/306:00 am
BOS
- PDX
Nonstop6h 11m
Alaska Airlines
Deal found 4/2![Alaska Airlines logo]()
$238
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 April 3, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated April 3, 2026.
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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
Deal found 3/30![Southwest logo]()
$125
This Super.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Sat 5/302:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Deal found 3/31![JetBlue logo]()
$132
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/262:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Deal found 3/31![JetBlue logo]()
$133
This Alaska Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 6/29:50 pm
PDX
- BOS
Nonstop5h 34m
Alaska Airlines
Deal found 4/2![Alaska Airlines logo]()
$134
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 6/3011:15 pm
PDX
- BOS
1 stop6h 52m
Delta
Deal found 4/2![Delta logo]()
$139
This Super.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Fri 5/222:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Deal found 3/31![JetBlue logo]()
$142
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 6/132:20 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Deal found 3/30![JetBlue logo]()
$143
This Alaska Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/309:56 pm
PDX
- BOS
Nonstop5h 24m
Alaska Airlines
Deal found 3/31![Alaska Airlines logo]()
$144
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 4/156:30 am
PDX
- BOS
2 stops10h 10m
Southwest
Deal found 4/1![Southwest logo]()
$149
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 7/12:10 pm
PDX
- BOS
1 stop8h 21m
Delta
Deal found 4/2![Delta logo]()
$154
This United Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/3010:55 pm
PDX
- BOS
1 stop7h 30m
United Airlines
Deal found 3/31![United Airlines logo]()
$155
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/2![Delta 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 April 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Delta) |
One-way from | $125 (Southwest) |
Popular in | December |
Cheapest in | May |
Average price | $380 |
Good round-trip deal | $325 or less |
Good one-way deal | $185 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 April 3, 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 5/5
10:15 pm-9:11 am
1 stop7h 56m
Boston Logan Intl
Tue 5/12
6:00 am-12:35 pm
1 stop9h 35m
$239
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
$288
PortlandBoston
PDX - BOS
PDXBOS
Portland
Tue 5/19
7:25 pm-8:15 am
2 stops9h 50m
Boston Logan Intl
Thu 6/4
4:45 pm-11:55 pm
1 stop10h 10m
$308
PortlandBoston
PDX - BOS
PDXBOS
Portland
Sat 5/16
9:46 pm-6:20 am
Nonstop5h 34m
Boston Logan Intl
Sat 5/23
6:40 pm-9:46 am
1 stop18h 06m
$312
PortlandBoston
PDX - BOS
PDXBOS
Portland
Fri 5/1
10:55 am-12:50 am
1 stop10h 55m
Boston Logan Intl
Mon 5/4
4:45 pm-12:10 am
2 stops10h 25m
$316
PortlandBoston
PDX - BOS
PDXBOS
Portland
Fri 5/1
10:55 am-11:10 pm
2 stops9h 15m
Boston Logan Intl
Fri 5/8
11:35 am-8:10 pm
2 stops11h 35m
$348
PortlandBoston
PDX - BOS
PDXBOS
Portland
Wed 4/29
11:59 pm-11:01 am
1 stop8h 02m
Boston Logan Intl
Wed 5/6
3:00 pm-10:35 pm
1 stop10h 35m
$349
PortlandBoston
PDX - BOS
PDXBOS
Portland
Wed 5/6
10:55 pm-12:51 pm
2 stops10h 56m
Boston Logan Intl
Wed 5/13
3:00 pm-10:35 pm
1 stop10h 35m
$352
PortlandBoston
PDX - BOS
PDXBOS
Portland
Fri 5/1
11:55 pm-1:51 pm
2 stops10h 56m
Boston Logan Intl
Sun 5/3
6:00 am-2:06 pm
1 stop11h 06m
$352
PortlandAlbany
PDX - ALB
PDXALB
Portland
Tue 4/28
5:40 am-3:40 pm
1 stop7h 00m
Albany Intl
Tue 5/5
12:20 pm-9:00 pm
2 stops11h 40m
$380
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-MVY
PDX-ALB
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Massachusetts
PDX-USMA
PDX-BOS
PDX-ACK
PDX-BDL
PDX-MVY
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 April 3, 2026.
It’s typically best to fly out from Portland to Massachusetts at noon. Doing so could potentially save you 40% 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 April 3, 2026.
The most flights from PDX to USMA are scheduled on a Thursday (4 on average). You will have fewer flight options on Saturday, 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?
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 April 3, 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.
Food
7.0
Comfort
7.8
Entertainment
7.0
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Comfort
7.8
Entertainment
7.0
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Comfort
7.8
Entertainment
7.0
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Comfort
7.8
Entertainment
7.0
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Comfort
7.8
Entertainment
7.0
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Comfort
7.8
Entertainment
7.0
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
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 April 3, 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 April 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$276 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$108 | Average$327 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$108 | Average$292 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$277 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$184 | Average$388 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$236 | Average$376 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$247 | Average$473 | FlexibilityNo cancel fee | On-time75% |