$129+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Jun 29 — Jul 61
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Massachusetts
Cheapest
Best
Last-minute
One-way
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 May 30, 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 May 30, 2026.
This American Airlines deal was found by Cheapflights users on 5/29. 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 8/2511:59 pm
PDX
- BDL
1 stop8h 47m
American Airlines
Wed 9/22:06 pm
BDL
- PDX
1 stop8h 42m
American Airlines
Deal found 5/29![American Airlines logo]()
$257
This United Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 9/411:02 pm
PDX
- BOS
1 stop7h 34m
United Airlines
Tue 9/83:35 pm
BOS
- PDX
1 stop9h 28m
United Airlines
Deal found 5/27![United Airlines logo]()
$280
This United Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 11/118:45 am
PDX
- BOS
1 stop8h 14m
United Airlines
Thu 11/124:57 pm
BOS
- PDX
1 stop8h 41m
United Airlines
Deal found 5/26![United Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 9/411:59 pm
PDX
- BOS
1 stop9h 11m
American Airlines
Sun 9/69:19 am
BOS
- PDX
1 stop11h 11m
American Airlines
Deal found 5/28![American Airlines logo]()
$282
This American Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/1011:41 pm
PDX
- BOS
1 stop9h 21m
American Airlines
Tue 7/145:10 am
BOS
- PDX
1 stop8h 26m
American Airlines
Deal found 5/26![American Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/310:30 pm
PDX
- BOS
1 stop8h 25m
American Airlines
Fri 7/106:01 am
BOS
- PDX
1 stop8h 32m
American Airlines
Deal found 5/26![American Airlines logo]()
$284
This Southwest deal was found by Cheapflights users on 5/29. 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 8/711:30 pm
PDX
- BOS
1 stop9h 55m
Southwest
Tue 8/252:45 pm
BOS
- PDX
2 stops10h 30m
Southwest
Deal found 5/29![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 5/29. 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 8/1811:30 pm
PDX
- BOS
1 stop7h 25m
Southwest
Tue 8/255:25 am
BOS
- PDX
1 stop8h 15m
Southwest
Deal found 5/29![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 8/1712:30 am
PDX
- ACK
2 stops12h 27m
Delta
Wed 8/263:24 pm
ACK
- PDX
1 stop8h 49m
Delta
Deal found 5/28![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 5/29. 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.
Thu 9/1012:40 pm
PDX
- BOS
2 stops14h 20m
Southwest
Tue 9/152:45 pm
BOS
- PDX
2 stops10h 30m
Southwest
Deal found 5/29![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 5/29. 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.
Mon 9/2110:45 pm
PDX
- BOS
1 stop7h 45m
Southwest
Mon 9/288:40 am
BOS
- PDX
2 stops17h 25m
Southwest
Deal found 5/29![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 5/29. 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 9/111:30 pm
PDX
- BDL
1 stop9h 30m
Southwest
Tue 9/156:00 am
BDL
- PDX
1 stop7h 40m
Southwest
Deal found 5/29![Southwest logo]()
$294
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 May 30, 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 May 30, 2026.
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 8/1011:30 pm
PDX
- BOS
1 stop7h 48m
United Airlines
Mon 8/245:01 pm
BOS
- PDX
1 stop8h 51m
United Airlines
Deal found 5/28![United Airlines logo]()
$282
This Southwest deal was found by Cheapflights users on 5/29. 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 9/2911:30 pm
PDX
- BOS
1 stop7h 25m
Southwest
Wed 10/141:15 pm
BOS
- PDX
2 stops11h 00m
Southwest
Deal found 5/29![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 5/30. 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 8/1712:30 am
PDX
- ACK
2 stops12h 27m
Delta
Wed 8/263:24 pm
ACK
- PDX
1 stop8h 49m
Delta
Deal found 5/30![Delta logo]()
$288
This Alaska Airlines deal was found by Cheapflights users on 5/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:36 pm
PDX
- BOS
Nonstop5h 33m
Alaska Airlines
Mon 8/316:17 pm
BOS
- PDX
1 stop18h 13m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$382
This JetBlue deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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
- ACK
1 stop7h 55m
JetBlue
Thu 8/273:43 pm
ACK
- PDX
1 stop9h 49m
JetBlue
Deal found 5/25![JetBlue logo]()
$517
This American Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 6/2610:59 pm
PDX
- HYA
1 stop13h 27m
American Airlines
Fri 7/312:45 pm
HYA
- PDX
2 stops14h 20m
American Airlines
Deal found 5/28![American Airlines logo]()
$530
This Southwest deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/511:35 pm
PDX
- BOS
2 stops10h 05m
Southwest
Wed 10/145:15 am
BOS
- PDX
1 stop14h 30m
Southwest
Deal found 5/25![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/1010:53 am
PDX
- BOS
1 stop9h 58m
Delta
Fri 7/171:35 pm
BOS
- PDX
1 stop10h 38m
Delta
Deal found 5/26![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 7/156:50 pm
PDX
- BOS
2 stops10h 27m
United Airlines
Tue 8/256:00 am
BOS
- PDX
1 stop8h 28m
United Airlines
Deal found 5/27![United Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 8/312:30 am
PDX
- BOS
1 stop7h 17m
Delta
Tue 8/116:05 am
BOS
- PDX
1 stop8h 36m
Delta
Deal found 5/27![Delta logo]()
$347
This Expedia deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/129:56 pm
PDX
- PVC
1 stop9h 37m
Multiple Airlines
Tue 6/1611:28 am
PVC
- PDX
1 stop12h 03m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$775
This United Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 9/2211:02 pm
PDX
- BOS
2 stops12h 48m
United Airlines
Sat 9/266:00 am
BOS
- PDX
2 stops12h 56m
United Airlines
Deal found 5/25![United Airlines logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/199:56 pm
PDX
- BOS
Nonstop5h 24m
Alaska Airlines
Wed 7/296:03 am
BOS
- PDX
Nonstop6h 16m
Alaska Airlines
Deal found 5/26![Alaska Airlines logo]()
$402
This Southwest deal was found by Cheapflights users on 5/29. 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 8/2111:30 pm
PDX
- BOS
2 stops11h 40m
Southwest
Mon 8/243:55 pm
BOS
- PDX
1 stop10h 10m
Southwest
Deal found 5/29![Southwest logo]()
$372
This Delta deal was found by Cheapflights users on 5/29. 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.
Tue 8/1812:30 am
PDX
- ACK
2 stops12h 27m
Delta
Tue 8/253:24 pm
ACK
- PDX
1 stop8h 49m
Delta
Deal found 5/29![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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
- ALB
1 stop8h 40m
Southwest
Mon 8/246:05 pm
ALB
- PDX
1 stop8h 00m
Southwest
Deal found 5/26![Southwest logo]()
$389
This United Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 10/211:30 pm
PDX
- ALB
1 stop7h 57m
United Airlines
Tue 10/68:00 am
ALB
- PDX
1 stop10h 05m
United Airlines
Deal found 5/26![United Airlines logo]()
$416
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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.
Sun 7/512:33 am
PDX
- BOS
1 stop7h 12m
Delta
Tue 7/145:30 am
BOS
- PDX
1 stop8h 06m
Delta
Deal found 5/26![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 10/155:00 am
PDX
- ALB
1 stop8h 35m
Southwest
Mon 10/195:00 am
ALB
- PDX
1 stop12h 40m
Southwest
Deal found 5/27![Southwest logo]()
$417
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 8/267:00 am
PDX
- ALB
2 stops13h 17m
Delta
Wed 9/26:00 am
ALB
- PDX
2 stops10h 38m
Delta
Deal found 5/28![Delta logo]()
$386
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 8/1211:30 pm
PDX
- ALB
1 stop8h 40m
Southwest
Mon 8/175:25 am
ALB
- PDX
1 stop12h 35m
Southwest
Deal found 5/26![Southwest logo]()
$421
This Delta deal was found by Cheapflights users on 5/30. 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.
Wed 10/1411:55 am
PDX
- ALB
1 stop8h 15m
Delta
Wed 10/2112:55 pm
ALB
- PDX
2 stops13h 56m
Delta
Deal found 5/30![Delta logo]()
$400
This United Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 10/208:30 am
PDX
- BDL
1 stop9h 52m
United Airlines
Wed 10/219:44 am
BDL
- PDX
1 stop9h 12m
United Airlines
Deal found 5/26![United Airlines logo]()
$485
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 9/106:05 am
PDX
- BDL
1 stop7h 05m
Southwest
Sun 9/131:00 pm
BDL
- PDX
1 stop8h 05m
Southwest
Deal found 5/27![Southwest logo]()
$430
This Delta deal was found by Cheapflights users on 5/30. 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.
Tue 10/1311:55 am
PDX
- ALB
1 stop8h 15m
Delta
Wed 10/2112:55 pm
ALB
- PDX
2 stops12h 09m
Delta
Deal found 5/30![Delta logo]()
$400
This JetBlue deal was found by Cheapflights users on 5/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/511:29 pm
PDX
- MVY
1 stop7h 39m
JetBlue
Thu 7/910:58 am
MVY
- PDX
1 stop29h 05m
JetBlue
Deal found 5/30![JetBlue logo]()
$717
This Southwest deal was found by Cheapflights users on 5/29. 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.
Thu 9/36:05 am
PDX
- BDL
2 stops8h 35m
Southwest
Mon 9/710:15 am
BDL
- PDX
1 stop7h 45m
Southwest
Deal found 5/29![Southwest logo]()
$430
This Delta deal was found by Cheapflights users on 5/29. 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.
Mon 6/2912:33 am
PDX
- ALB
2 stops12h 49m
Delta
Tue 7/1412:27 pm
ALB
- PDX
2 stops12h 33m
Delta
Deal found 5/29![Delta logo]()
$405
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Fri 8/1411:34 pm
PDX
- MVY
2 stops12h 10m
American Airlines
Sun 8/233:00 pm
MVY
- PDX
1 stop9h 58m
American Airlines
Deal found 5/29![American Airlines logo]()
$798
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 9/106:05 am
PDX
- ALB
1 stop7h 20m
Southwest
Sun 9/135:40 am
ALB
- PDX
1 stop7h 50m
Southwest
Deal found 5/27![Southwest logo]()
$430
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated May 30, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated May 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/16:15 am
PDX
- BOS
1 stop9h 31m
American Airlines
Tue 6/163:10 pm
BOS
- PDX
1 stop11h 37m
American Airlines
Deal found 5/26![American Airlines logo]()
$315
This Expedia deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 6/89:46 pm
PDX
- BOS
Nonstop5h 34m
Multiple Airlines
Mon 6/159:57 am
BOS
- PDX
Nonstop6h 08m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/811:30 pm
PDX
- BOS
1 stop9h 45m
Southwest
Wed 6/105:50 am
BOS
- PDX
2 stops11h 05m
Southwest
Deal found 5/26![Southwest logo]()
$319
This American Airlines deal was found by Cheapflights users on 5/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:10 am
PDX
- BOS
1 stop8h 57m
American Airlines
Tue 6/165:31 am
BOS
- PDX
1 stop9h 03m
American Airlines
Deal found 5/30![American Airlines logo]()
$320
This Alaska Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/105:40 pm
PDX
- BOS
1 stop9h 00m
Alaska Airlines
Tue 6/166:03 am
BOS
- PDX
Nonstop6h 16m
Alaska Airlines
Deal found 5/26![Alaska Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/102:27 pm
PDX
- BOS
1 stop7h 47m
United Airlines
Mon 6/154:15 pm
BOS
- PDX
1 stop8h 33m
United Airlines
Deal found 5/27![United Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/102:10 pm
PDX
- BOS
1 stop8h 21m
Delta
Tue 6/163:40 pm
BOS
- PDX
1 stop11h 14m
Delta
Deal found 5/26![Delta logo]()
$322
This Alaska Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/109:56 pm
PDX
- BOS
Nonstop5h 24m
Alaska Airlines
Wed 6/176:03 am
BOS
- PDX
Nonstop6h 16m
Alaska Airlines
Deal found 5/27![Alaska Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/1110:40 pm
PDX
- BOS
1 stop7h 49m
United Airlines
Tue 6/165:05 pm
BOS
- PDX
1 stop8h 24m
United Airlines
Deal found 5/27![United Airlines logo]()
$280
This United Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 6/126:50 pm
PDX
- BOS
1 stop8h 08m
United Airlines
Tue 6/165:05 pm
BOS
- PDX
1 stop8h 24m
United Airlines
Deal found 5/25![United Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Fri 6/1210:40 pm
PDX
- BOS
1 stop8h 21m
American Airlines
Tue 6/165:31 am
BOS
- PDX
1 stop9h 03m
American Airlines
Deal found 5/29![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/301:45 pm
PDX
- ALB
1 stop7h 27m
American Airlines
Tue 7/146:21 am
ALB
- PDX
1 stop8h 12m
American Airlines
Deal found 5/27![American Airlines logo]()
$375
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 May 30, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated May 30, 2026.
This Delta deal was found by Cheapflights users on 5/29. 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.
Tue 8/1112:30 am
PDX
- BDL
1 stop7h 24m
Delta
Deal found 5/29![Delta logo]()
$129
This United Airlines deal was found by Cheapflights users on 5/29. 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 8/2511:02 pm
PDX
- BDL
2 stops12h 03m
United Airlines
Deal found 5/29![United Airlines logo]()
$134
This Cheapflightsfares deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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.
Wed 6/102:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Deal found 5/26![JetBlue logo]()
$138
This Alaska Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/109:56 pm
PDX
- BOS
Nonstop5h 24m
Alaska Airlines
Deal found 5/26![Alaska Airlines logo]()
$139
This Southwest deal was found by Cheapflights users on 5/29. 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 8/2511:30 pm
PDX
- BOS
2 stops10h 10m
Southwest
Deal found 5/29![Southwest logo]()
$141
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 9/21:25 pm
PDX
- BOS
1 stop7h 40m
Southwest
Deal found 5/27![Southwest logo]()
$143
This Southwest deal was found by Cheapflights users on 5/29. 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.
Wed 8/1211:30 pm
PDX
- BDL
1 stop9h 30m
Southwest
Deal found 5/29![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 9/2211:30 pm
PDX
- BOS
2 stops10h 10m
Southwest
Deal found 5/27![Southwest logo]()
$148
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/102:10 pm
PDX
- BOS
1 stop8h 21m
Delta
Deal found 5/26![Delta logo]()
$149
This American Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/710:30 pm
PDX
- BOS
1 stop8h 25m
American Airlines
Deal found 5/26![American Airlines logo]()
$150
This Cheapflightsfares deal was found by Cheapflights users on 5/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2611:44 pm
PDX
- BOS
Nonstop5h 20m
JetBlue
Deal found 5/29![JetBlue logo]()
$154
This American Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 8/295:18 am
PDX
- BOS
1 stop11h 24m
American Airlines
Deal found 5/28![American Airlines logo]()
$156
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 May 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (American Airlines) |
One-way from | $129 (Delta) |
Popular in | December |
Cheapest in | August |
Average price | $402 |
Good round-trip deal | $376 or less |
Good one-way deal | $164 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 May 30, 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
Mon 8/10
11:30 pm-10:18 am
1 stop7h 48m
Boston Logan Intl
Mon 8/24
5:01 pm-10:52 pm
1 stop8h 51m
$282
PortlandBoston
PDX - BOS
PDXBOS
Portland
Tue 9/29
11:30 pm-9:55 am
1 stop7h 25m
Boston Logan Intl
Wed 10/14
1:15 pm-9:15 pm
2 stops11h 00m
$285
PortlandNantucket
PDX - ACK
PDXACK
Portland
Mon 8/17
12:30 am-3:57 pm
2 stops12h 27m
Nantucket Memorial
Wed 8/26
3:24 pm-9:13 pm
1 stop8h 49m
$288
PortlandBoston
PDX - BOS
PDXBOS
Portland
Mon 10/5
11:35 pm-12:40 pm
2 stops10h 05m
Boston Logan Intl
Wed 10/14
5:15 am-4:45 pm
1 stop14h 30m
$309
PortlandBoston
PDX - BOS
PDXBOS
Portland
Fri 7/10
10:53 am-11:51 pm
1 stop9h 58m
Boston Logan Intl
Fri 7/17
1:35 pm-9:13 pm
1 stop10h 38m
$337
PortlandBoston
PDX - BOS
PDXBOS
Portland
Mon 8/3
12:30 am-10:47 am
1 stop7h 17m
Boston Logan Intl
Tue 8/11
6:05 am-11:41 am
1 stop8h 36m
$347
PortlandBoston
PDX - BOS
PDXBOS
Portland
Wed 7/15
6:50 pm-8:17 am
2 stops10h 27m
Boston Logan Intl
Tue 8/25
6:00 am-11:28 am
1 stop8h 28m
$352
PortlandBoston
PDX - BOS
PDXBOS
Portland
Tue 9/22
11:02 pm-2:50 pm
2 stops12h 48m
Boston Logan Intl
Sat 9/26
6:00 am-3:56 pm
2 stops12h 56m
$357
PortlandBoston
PDX - BOS
PDXBOS
Portland
Fri 8/21
11:30 pm-2:10 pm
2 stops11h 40m
Boston Logan Intl
Mon 8/24
3:55 pm-11:05 pm
1 stop10h 10m
$372
PortlandNantucket
PDX - ACK
PDXACK
Portland
Tue 8/18
12:30 am-3:57 pm
2 stops12h 27m
Nantucket Memorial
Tue 8/25
3:24 pm-9:13 pm
1 stop8h 49m
$373
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-BDL
PDX-BOS
PDX-ACK
PDX-HYA
PDX-PVC
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-BDL
PDX-BOS
PDX-ACK
PDX-HYA
What is the cheapest month to book a flight from Portland to Massachusetts?
Currently, April is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $60). Flying from Portland to Massachusetts in January is currently the most expensive (average of $142). 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 May 30, 2026.
It’s typically best to fly out from Portland to Massachusetts at noon. Doing so could potentially save you 27% 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 May 30, 2026.
The most flights from PDX to USMA are scheduled on a Monday (3 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 62 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 May 30, 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
Entertainment
7.0
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Entertainment
7.0
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Entertainment
7.0
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Entertainment
7.0
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Entertainment
7.0
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Entertainment
7.0
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.1
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Portland to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from 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 May 30, 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 May 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$345 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$118 | Average$282 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$149 | Average$334 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$282 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$184 | Average$390 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$236 | Average$384 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$271 | Average$496 | FlexibilityNo cancel fee | On-time75% |