$131+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Jul 10 — Jul 171
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 June 10, 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 June 10, 2026.
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/15:18 am
PDX
- BDL
1 stop11h 16m
American Airlines
Tue 9/156:24 pm
BDL
- PDX
1 stop8h 43m
American Airlines
Deal found 6/10![American Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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
- BDL
2 stops9h 40m
Southwest
Tue 9/296:00 am
BDL
- PDX
1 stop7h 40m
Southwest
Deal found 6/9![Southwest logo]()
$254
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 10/2112:32 pm
PDX
- ALB
1 stop7h 46m
American Airlines
Tue 10/276:00 am
ALB
- PDX
1 stop8h 32m
American Airlines
Deal found 6/9![American Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 10/2111:55 am
PDX
- ALB
1 stop8h 15m
Delta
Tue 10/275:00 pm
ALB
- PDX
2 stops9h 52m
Delta
Deal found 6/8![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/86:04 am
PDX
- ALB
2 stops13h 48m
Delta
Wed 9/3012:32 pm
ALB
- PDX
2 stops10h 44m
Delta
Deal found 6/8![Delta logo]()
$271
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:59 pm
PDX
- BDL
1 stop8h 21m
American Airlines
Wed 9/25:41 pm
BDL
- PDX
1 stop9h 18m
American Airlines
Deal found 6/9![American Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/1511:30 pm
PDX
- BDL
2 stops9h 40m
Southwest
Sat 9/195:50 am
BDL
- PDX
1 stop9h 40m
Southwest
Deal found 6/9![Southwest logo]()
$278
This JetBlue deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/611:27 pm
PDX
- ACK
1 stop10h 36m
JetBlue
Mon 7/133:33 pm
ACK
- PDX
1 stop9h 58m
JetBlue
Deal found 6/6![JetBlue logo]()
$279
This JetBlue deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/9![JetBlue logo]()
$280
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 stops12h 22m
Delta
Wed 8/263:24 pm
ACK
- PDX
1 stop8h 49m
Delta
Deal found 6/8![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 9/97:05 am
PDX
- BOS
2 stops11h 20m
Southwest
Wed 9/165:25 am
BOS
- PDX
1 stop8h 15m
Southwest
Deal found 6/5![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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
Wed 8/125:25 am
BOS
- PDX
1 stop8h 15m
Southwest
Deal found 6/5![Southwest logo]()
$287
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 June 10, 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 June 10, 2026.
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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
- BDL
1 stop8h 36m
United Airlines
Tue 9/295:03 pm
BDL
- PDX
1 stop8h 20m
United Airlines
Deal found 6/9![United Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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
- BDL
2 stops9h 40m
Southwest
Tue 9/296:00 am
BDL
- PDX
1 stop7h 40m
Southwest
Deal found 6/9![Southwest logo]()
$254
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 6/5![JetBlue logo]()
$280
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 stops12h 22m
Delta
Wed 8/263:24 pm
ACK
- PDX
1 stop8h 49m
Delta
Deal found 6/7![Delta logo]()
$286
This Alaska Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/49:36 pm
PDX
- BOS
Nonstop5h 33m
Alaska Airlines
Mon 9/78:00 am
BOS
- PDX
1 stop32h 50m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/1410:30 pm
PDX
- HYA
1 stop10h 45m
American Airlines
Tue 7/211:26 pm
HYA
- PDX
2 stops14h 24m
American Airlines
Deal found 6/5![American Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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
- ALB
1 stop9h 05m
Southwest
Wed 9/306:20 pm
ALB
- PDX
1 stop7h 50m
Southwest
Deal found 6/8![Southwest logo]()
$261
This Priceline deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:27 pm
PDX
- ACK
1 stop7h 55m
JetBlue
Mon 7/133:33 pm
ACK
- PDX
1 stop9h 58m
JetBlue
Deal found 6/5![JetBlue logo]()
$280
This Expedia deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/611:27 pm
PDX
- EWB
2 stops13h 18m
Multiple Airlines
Sun 7/127:00 am
EWB
- PDX
2 stops18h 48m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$574
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 10/1511:39 am
PDX
- ALB
2 stops8h 31m
Delta
Mon 10/196:00 am
ALB
- PDX
2 stops9h 29m
Delta
Deal found 6/8![Delta logo]()
$323
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:00 am
PDX
- BOS
1 stop13h 25m
Southwest
Sat 8/227:05 am
BOS
- PDX
1 stop8h 25m
Southwest
Deal found 6/6![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/1711:35 am
PDX
- BOS
1 stop9h 24m
Delta
Mon 9/216:05 am
BOS
- PDX
1 stop8h 30m
Delta
Deal found 6/9![Delta logo]()
$347
This Alaska Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/69:19 am
PDX
- BOS
1 stop11h 40m
Alaska Airlines
Mon 7/136:03 am
BOS
- PDX
Nonstop6h 16m
Alaska Airlines
Deal found 6/5![Alaska Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 10/2011:35 pm
PDX
- BOS
2 stops10h 05m
Southwest
Sat 10/241:25 pm
BOS
- PDX
2 stops11h 10m
Southwest
Deal found 6/5![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 10/212:36 pm
PDX
- BOS
1 stop8h 46m
Delta
Thu 10/86:00 am
BOS
- PDX
1 stop8h 50m
Delta
Deal found 6/9![Delta logo]()
$347
This Alaska Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/155:40 pm
PDX
- BOS
1 stop9h 00m
Alaska Airlines
Wed 7/226:03 am
BOS
- PDX
Nonstop6h 16m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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
- ALB
1 stop8h 22m
United Airlines
Wed 9/234:53 pm
ALB
- PDX
1 stop8h 59m
United Airlines
Deal found 6/9![United Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/1812:35 am
PDX
- ACK
2 stops11h 06m
Delta
Tue 8/253:24 pm
ACK
- PDX
1 stop8h 49m
Delta
Deal found 6/10![Delta logo]()
$350
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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
Wed 8/122:10 pm
BOS
- PDX
2 stops11h 05m
Southwest
Deal found 6/6![Southwest logo]()
$352
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 6/306:15 am
PDX
- ALB
1 stop10h 15m
American Airlines
Tue 7/146:21 am
ALB
- PDX
1 stop8h 12m
American Airlines
Deal found 6/5![American Airlines logo]()
$486
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/110:55 pm
PDX
- BDL
1 stop8h 30m
Delta
Tue 9/1511:35 am
BDL
- PDX
2 stops13h 27m
Delta
Deal found 6/10![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/183:40 pm
PDX
- BOS
1 stop11h 20m
Southwest
Sun 9/205:30 am
BOS
- PDX
2 stops11h 35m
Southwest
Deal found 6/9![Southwest logo]()
$367
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:40 pm
PDX
- BDL
1 stop7h 33m
United Airlines
Wed 11/1810:23 am
BDL
- PDX
2 stops13h 10m
United Airlines
Deal found 6/6![United Airlines logo]()
$496
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/1011:15 pm
PDX
- HYA
2 stops12h 09m
American Airlines
Sat 7/183:02 pm
HYA
- PDX
2 stops12h 48m
American Airlines
Deal found 6/9![American Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/2711:20 pm
PDX
- BDL
1 stop6h 28m
Delta
Sun 8/305:30 am
BDL
- PDX
1 stop7h 56m
Delta
Deal found 6/9![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/207:00 pm
PDX
- BDL
2 stops11h 40m
Southwest
Mon 8/241:40 pm
BDL
- PDX
1 stop10h 05m
Southwest
Deal found 6/8![Southwest logo]()
$371
This KAYAK deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/2011:27 pm
PDX
- EWB
2 stops13h 18m
Multiple Airlines
Fri 8/287:00 am
EWB
- PDX
2 stops18h 32m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$642
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/77:55 pm
PDX
- BDL
2 stops11h 35m
Southwest
Mon 8/106:20 pm
BDL
- PDX
1 stop7h 45m
Southwest
Deal found 6/9![Southwest logo]()
$371
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 6/209:57 pm
PDX
- HYA
2 stops11h 14m
American Airlines
Wed 6/2412:42 pm
HYA
- PDX
2 stops13h 09m
American Airlines
Deal found 6/5![American Airlines logo]()
$558
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/411:20 pm
PDX
- BDL
1 stop9h 54m
Delta
Sun 9/65:50 am
BDL
- PDX
1 stop7h 36m
Delta
Deal found 6/9![Delta logo]()
$408
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated June 10, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/2610:27 am
PDX
- BOS
1 stop8h 26m
United Airlines
Sat 7/49:40 am
BOS
- PDX
1 stop8h 29m
United Airlines
Deal found 6/7![United Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/8![American Airlines logo]()
$311
This Flysmarter deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:29 pm
PDX
- BOS
Nonstop5h 23m
JetBlue
Fri 7/107:19 pm
BOS
- PDX
Nonstop6h 12m
JetBlue
Deal found 6/8![JetBlue logo]()
$319
This Expedia deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/311:29 pm
PDX
- BOS
Nonstop5h 23m
Multiple Airlines
Fri 7/106:03 am
BOS
- PDX
Nonstop6h 16m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$326
This JetBlue deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/611:27 pm
PDX
- ACK
1 stop10h 36m
JetBlue
Mon 7/133:33 pm
ACK
- PDX
1 stop9h 58m
JetBlue
Deal found 6/6![JetBlue logo]()
$279
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/610:30 pm
PDX
- BOS
1 stop10h 33m
American Airlines
Mon 7/135:52 pm
BOS
- PDX
1 stop10h 03m
American Airlines
Deal found 6/9![American Airlines logo]()
$292
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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.
Wed 7/82:16 pm
PDX
- BOS
Nonstop5h 24m
JetBlue
Fri 7/107:19 pm
BOS
- PDX
Nonstop6h 12m
JetBlue
Deal found 6/8![JetBlue logo]()
$327
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Thu 7/911:27 pm
PDX
- BOS
Nonstop5h 21m
JetBlue
Mon 7/137:19 pm
BOS
- PDX
Nonstop6h 12m
JetBlue
Deal found 6/10![JetBlue logo]()
$322
This Priceline deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:27 pm
PDX
- ACK
1 stop7h 55m
JetBlue
Mon 7/133:33 pm
ACK
- PDX
1 stop9h 58m
JetBlue
Deal found 6/5![JetBlue logo]()
$280
This lol.travel deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:27 pm
PDX
- BOS
Nonstop5h 21m
JetBlue
Tue 7/149:55 am
BOS
- PDX
Nonstop6h 08m
JetBlue
Deal found 6/10![JetBlue logo]()
$320
This American Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/1110:30 pm
PDX
- BOS
1 stop7h 13m
American Airlines
Sun 7/196:01 am
BOS
- PDX
1 stop8h 32m
American Airlines
Deal found 6/7![American Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/225:07 am
PDX
- BOS
1 stop8h 48m
American Airlines
Mon 8/106:00 am
BOS
- PDX
1 stop8h 50m
American Airlines
Deal found 6/9![American Airlines logo]()
$315
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 June 10, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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
Deal found 6/8![Southwest logo]()
$131
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/1711:30 pm
PDX
- BOS
1 stop7h 25m
Southwest
Deal found 6/8![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 10/2011:35 pm
PDX
- BOS
2 stops10h 05m
Southwest
Deal found 6/9![Southwest logo]()
$138
This JetBlue deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2711:29 pm
PDX
- MVY
1 stop7h 39m
JetBlue
Deal found 6/6![JetBlue logo]()
$140
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/611:40 pm
PDX
- BOS
1 stop8h 25m
United Airlines
Deal found 6/7![United Airlines logo]()
$141
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/138:00 am
PDX
- BOS
1 stop13h 25m
Southwest
Deal found 6/8![Southwest logo]()
$142
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/412:35 am
PDX
- BDL
1 stop7h 19m
Delta
Deal found 6/8![Delta logo]()
$147
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/1510:30 pm
PDX
- BOS
1 stop7h 13m
American Airlines
Deal found 6/9![American Airlines logo]()
$149
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/55:18 am
PDX
- BOS
1 stop11h 24m
American Airlines
Deal found 6/9![American Airlines logo]()
$151
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/196:45 am
PDX
- ALB
2 stops13h 32m
Delta
Deal found 6/9![Delta logo]()
$152
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/215:49 am
PDX
- BOS
1 stop9h 15m
American Airlines
Deal found 6/5![American Airlines logo]()
$154
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/3111:30 pm
PDX
- BOS
1 stop9h 45m
Southwest
Deal found 6/5![Southwest logo]()
$158
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 June 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $249 (American Airlines) |
One-way from | $131 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $420 |
Good round-trip deal | $386 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 June 10, 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
PortlandHartford
PDX - BDL
PDXBDL
Portland
Tue 9/22
11:02 pm-10:38 am
1 stop8h 36m
Hartford Bradley Intl
Tue 9/29
5:03 pm-10:23 pm
1 stop8h 20m
$249
PortlandHartford
PDX - BDL
PDXBDL
Portland
Tue 9/22
11:30 pm-12:10 pm
2 stops9h 40m
Hartford Bradley Intl
Tue 9/29
6:00 am-10:40 am
1 stop7h 40m
$254
PortlandAlbany
PDX - ALB
PDXALB
Portland
Tue 9/8
11:30 pm-11:35 am
1 stop9h 05m
Albany Intl
Wed 9/30
6:20 pm-11:10 pm
1 stop7h 50m
$261
PortlandNantucket
PDX - ACK
PDXACK
Portland
Mon 8/24
11:27 pm-10:22 am
1 stop7h 55m
Nantucket Memorial
Thu 8/27
3:43 pm-10:32 pm
1 stop9h 49m
$280
PortlandNantucket
PDX - ACK
PDXACK
Portland
Fri 7/10
11:27 pm-10:22 am
1 stop7h 55m
Nantucket Memorial
Mon 7/13
3:33 pm-10:31 pm
1 stop9h 58m
$280
PortlandNantucket
PDX - ACK
PDXACK
Portland
Mon 8/17
12:35 am-3:57 pm
2 stops12h 22m
Nantucket Memorial
Wed 8/26
3:24 pm-9:13 pm
1 stop8h 49m
$286
PortlandBoston
PDX - BOS
PDXBOS
Portland
Sat 8/8
8:00 am-12:25 am
1 stop13h 25m
Boston Logan Intl
Sat 8/22
7:05 am-12:30 pm
1 stop8h 25m
$297
PortlandAlbany
PDX - ALB
PDXALB
Portland
Thu 10/15
11:39 am-11:10 pm
2 stops8h 31m
Albany Intl
Mon 10/19
6:00 am-12:29 pm
2 stops9h 29m
$323
PortlandBoston
PDX - BOS
PDXBOS
Portland
Tue 10/20
11:35 pm-12:40 pm
2 stops10h 05m
Boston Logan Intl
Sat 10/24
1:25 pm-9:35 pm
2 stops11h 10m
$346
PortlandBoston
PDX - BOS
PDXBOS
Portland
Thu 9/17
11:35 am-11:59 pm
1 stop9h 24m
Boston Logan Intl
Mon 9/21
6:05 am-11:35 am
1 stop8h 30m
$347
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-ALB
PDX-ACK
PDX-BOS
PDX-MVY
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Massachusetts
PDX-USMA
PDX-BDL
PDX-ALB
PDX-ACK
PDX-BOS
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 October is currently the most expensive (average of $162). 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 June 10, 2026.
It’s typically best to fly out from Portland to Massachusetts at noon. Doing so could potentially save you 25% 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 June 10, 2026.
The most flights from PDX to USMA are scheduled on a Wednesday (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 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 June 10, 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.
Comfort
7.8
Overall
7.9
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Overall
7.9
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Overall
7.9
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Overall
7.9
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Overall
7.9
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Overall
7.9
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
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 June 10, 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 June 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$382 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$116 | Average$283 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$166 | Average$356 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$283 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$184 | Average$389 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$236 | Average$371 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$278 | Average$505 | FlexibilityNo cancel fee | On-time75% |