$169+ Cheap flights from Portland (PDX) to Massachusetts
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Oct 11 — Oct 181
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 September 11, 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 September 11, 2026.
This SmartFares deal was found by Cheapflights users on 9/10. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:44 pm -
Nonstop5h 28m
Sat 10/244:46 pm -
Nonstop6h 14m
Deal found 9/10![Alaska Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 10/279:44 pm -
1 stop8h 21m
Thu 11/512:22 pm -
1 stop10h 25m
Deal found 9/9![American Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:35 pm -
1 stop8h 25m
Tue 11/35:40 am -
2 stops10h 30m
Deal found 9/10![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:35 pm -
2 stops9h 40m
Mon 11/22:30 pm -
2 stops12h 25m
Deal found 9/10![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 9/9. 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 10/278:35 am -
2 stops10h 45m
Thu 11/511:50 am -
1 stop11h 30m
Deal found 9/9![Southwest logo]()
$348
This Delta deal was found by Cheapflights users on 9/8. 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.
Fri 10/1611:12 pm -
1 stop9h 50m
Wed 10/215:23 am -
1 stop8h 18m
Deal found 9/8![Delta logo]()
$352
This lol.travel deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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.
Sat 10/317:03 am -
Nonstop5h 40m
Sat 11/79:03 am -
Nonstop6h 20m
Deal found 9/11![Alaska Airlines logo]()
$352
This SmartFares deal was found by Cheapflights users on 9/7. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:53 pm -
1 stop11h 28m
Wed 10/2810:07 am -
Nonstop6h 12m
Deal found 9/7![Alaska Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 9/8. 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 10/1911:35 pm -
1 stop8h 20m
Thu 10/224:25 pm -
2 stops10h 50m
Deal found 9/8![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 9/8. 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 10/288:35 am -
2 stops9h 40m
Sat 10/317:20 am -
2 stops13h 55m
Deal found 9/8![Southwest logo]()
$362
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:44 pm -
Nonstop5h 28m
Wed 10/2810:07 am -
Nonstop6h 12m
Deal found 9/10![Alaska Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 9/9. 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.
Mon 10/1911:00 pm -
1 stop9h 15m
Wed 10/2812:20 pm -
1 stop9h 49m
Deal found 9/9![Delta logo]()
$363
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 September 11, 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 September 11, 2026.
This United Airlines deal was found by Cheapflights users on 9/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:00 am -
1 stop7h 56m
Sat 10/317:35 am -
1 stop8h 50m
Deal found 9/8![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 9/8. 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 11/97:00 pm -
2 stops9h 55m
Thu 11/126:40 pm -
1 stop8h 15m
Deal found 9/8![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 9/8. 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 10/2711:00 pm -
1 stop9h 15m
Sat 10/316:00 am -
1 stop7h 41m
Deal found 9/8![Delta logo]()
$363
This Alaska Airlines deal was found by Cheapflights users on 9/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:44 pm -
Nonstop5h 28m
Sat 10/314:58 pm -
1 stop9h 04m
Deal found 9/6![Alaska Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:35 am -
2 stops10h 07m
Tue 11/36:00 am -
1 stop8h 52m
Deal found 9/10![United Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 9/9. 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 10/2911:00 pm -
2 stops10h 00m
Mon 11/26:00 am -
1 stop7h 41m
Deal found 9/9![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:05 pm -
2 stops10h 10m
Sat 10/318:30 am -
2 stops12h 45m
Deal found 9/10![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:59 pm -
1 stop7h 28m
Sat 10/314:55 pm -
1 stop8h 32m
Deal found 9/10![United Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 9/9. 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 10/2911:52 am -
1 stop8h 58m
Sat 10/316:10 am -
2 stops13h 00m
Deal found 9/9![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 9/8. 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 10/197:35 pm -
2 stops9h 40m
Thu 10/224:25 pm -
2 stops10h 50m
Deal found 9/8![Southwest logo]()
$377
This Alaska Airlines deal was found by Cheapflights users on 9/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/255:02 am -
1 stop9h 04m
Tue 1/54:56 pm -
Nonstop6h 25m
Deal found 9/8![Alaska Airlines logo]()
$417
This KAYAK deal was found by Cheapflights users on 9/8. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/189:50 pm -
1 stop16h 19m
Thu 12/317:30 am -
1 stop29h 10m
Deal found 9/8![Multiple Airlines logo]()
$854
This Delta deal was found by Cheapflights users on 9/9. 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 10/2211:52 am -
1 stop8h 58m
Tue 10/275:18 pm -
2 stops9h 26m
Deal found 9/9![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2611:35 pm -
1 stop8h 20m
Sat 10/318:10 am -
1 stop8h 15m
Deal found 9/7![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:20 am -
2 stops12h 00m
Tue 11/1712:30 pm -
2 stops12h 15m
Deal found 9/7![Southwest logo]()
$380
This Alaska Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/1110:59 pm -
Nonstop5h 21m
Sat 11/147:03 am -
1 stop29h 40m
Deal found 9/11![Alaska Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 9/9. 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 12/2511:42 am -
1 stop8h 56m
Mon 1/42:20 pm -
1 stop11h 06m
Deal found 9/9![Delta logo]()
$404
This United Airlines deal was found by Cheapflights users on 9/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/307:49 pm -
2 stops15h 26m
Wed 2/36:00 am -
2 stops12h 30m
Deal found 9/8![United Airlines logo]()
$458
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 10/316:20 am -
1 stop7h 45m
Sat 11/710:40 am -
2 stops12h 25m
Deal found 9/9![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:12 pm -
1 stop6h 35m
Mon 10/195:23 am -
1 stop8h 18m
Deal found 9/6![Delta logo]()
$417
This Southwest deal was found by Cheapflights users on 9/9. 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.
Mon 2/2210:55 am -
1 stop7h 05m
Sat 2/2712:55 pm -
2 stops12h 20m
Deal found 9/9![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/216:50 am -
2 stops8h 35m
Sat 1/239:40 am -
2 stops10h 35m
Deal found 9/7![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:51 am -
2 stops11h 06m
Sat 10/106:00 am -
1 stop7h 41m
Deal found 9/6![Delta logo]()
$445
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:00 pm -
2 stops10h 05m
Sun 11/157:05 am -
1 stop8h 40m
Deal found 9/10![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 9/8. 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 9/282:10 pm -
1 stop8h 07m
Wed 9/305:55 am -
1 stop7h 54m
Deal found 9/8![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 9/8. 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.
Sat 9/267:10 am -
1 stop9h 05m
Tue 9/297:05 am -
1 stop8h 32m
Deal found 9/8![Delta logo]()
$447
This Southwest deal was found by Cheapflights users on 9/6. 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.
Sun 10/2511:35 pm -
1 stop8h 25m
Fri 10/306:50 am -
1 stop8h 20m
Deal found 9/6![Southwest logo]()
$419
This KAYAK deal was found by Cheapflights users on 9/8. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/189:50 pm -
1 stop16h 19m
Fri 1/17:30 am -
1 stop29h 10m
Deal found 9/8![Multiple Airlines logo]()
$924
This Southwest deal was found by Cheapflights users on 9/6. 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.
Mon 10/267:35 pm -
2 stops9h 40m
Fri 10/3012:30 pm -
2 stops11h 45m
Deal found 9/6![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/211:30 pm -
2 stops9h 50m
Mon 11/92:25 pm -
2 stops12h 30m
Deal found 9/11![Southwest logo]()
$427
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated September 11, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/8. 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.
Fri 10/1611:12 pm -
1 stop9h 50m
Wed 10/215:23 am -
1 stop8h 18m
Deal found 9/8![Delta logo]()
$352
This SmartFares deal was found by Cheapflights users on 9/10. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:44 pm -
Nonstop5h 28m
Sat 10/244:46 pm -
Nonstop6h 14m
Deal found 9/10![Alaska Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 9/8. 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 10/1911:35 pm -
1 stop8h 20m
Thu 10/224:25 pm -
2 stops10h 50m
Deal found 9/8![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 9/9. 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.
Mon 10/1911:12 pm -
1 stop6h 46m
Tue 10/276:00 am -
1 stop7h 41m
Deal found 9/9![Delta logo]()
$363
This SmartFares deal was found by Cheapflights users on 9/7. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:53 pm -
1 stop11h 28m
Wed 10/2810:07 am -
Nonstop6h 12m
Deal found 9/7![Alaska Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:35 pm -
2 stops9h 40m
Mon 11/22:30 pm -
2 stops12h 25m
Deal found 9/10![Southwest logo]()
$347
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 10/279:44 pm -
1 stop8h 21m
Thu 11/512:22 pm -
1 stop10h 25m
Deal found 9/9![American Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 9/9. 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 10/278:35 am -
2 stops10h 45m
Thu 11/511:50 am -
1 stop11h 30m
Deal found 9/9![Southwest logo]()
$348
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:44 pm -
Nonstop5h 28m
Wed 10/2810:07 am -
Nonstop6h 12m
Deal found 9/10![Alaska Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 9/8. 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 10/288:35 am -
2 stops9h 40m
Sat 10/317:20 am -
2 stops13h 55m
Deal found 9/8![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:35 pm -
1 stop8h 25m
Tue 11/35:40 am -
2 stops10h 30m
Deal found 9/10![Southwest logo]()
$342
This lol.travel deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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.
Sat 10/317:03 am -
Nonstop5h 40m
Sat 11/79:03 am -
Nonstop6h 20m
Deal found 9/11![Alaska Airlines logo]()
$352
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 September 11, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Delta deal was found by Cheapflights users on 9/10. 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.
Mon 10/1911:12 pm -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/297:35 pm -
2 stops9h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Southwest logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:02 pm -
3 stops23h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/1611:20 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Delta logo]()
$179
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1911:30 pm -
1 stop8h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$182
This Alaska Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/77:03 am -
Nonstop5h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Alaska Airlines logo]()
$184
This Delta deal was found by Cheapflights users on 9/10. 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.
Mon 10/198:44 pm -
2 stops11h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$187
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/247:05 am -
1 stop10h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![American Airlines logo]()
$188
This Southwest deal was found by Cheapflights users on 9/9. 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.
Mon 10/197:35 pm -
2 stops9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$189
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Wed 10/710:33 pm -
1 stop8h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![United Airlines logo]()
$189
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:53 pm -
1 stop11h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Alaska Airlines logo]()
$192
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/107:10 am -
1 stop9h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![United Airlines logo]()
$194
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 September 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $335 (SmartFares) |
One-way from | $169 (Delta) |
Popular in | December |
Cheapest in | January |
Average price | $411 |
Good round-trip deal | $391 or less |
Good one-way deal | $228 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 7,457,451 searches. Data last updated September 11, 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 Portland - BDL Hartford Bradley Intl
PDXBDL
Portland
Mon 11/16
11:20 pm-12:12 pm
1 stop9h 52m
Hartford Bradley Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$169
PortlandHartford
PDX Portland - BDL Hartford Bradley Intl
PDXBDL
Portland
Mon 10/19
11:35 pm-10:55 am
1 stop8h 20m
Hartford Bradley Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$169
PortlandHartford
PDX Portland - BDL Hartford Bradley Intl
PDXBDL
Portland
Thu 10/29
11:30 pm-10:43 am
1 stop8h 13m
Hartford Bradley Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$169
PortlandHartford
PDX Portland - BDL Hartford Bradley Intl
PDXBDL
Portland
Wed 12/2
11:53 am-11:43 pm
1 stop8h 50m
Hartford Bradley Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$169
PortlandHartford
PDX Portland - BDL Hartford Bradley Intl
PDXBDL
Portland
Sat 10/24
11:59 pm-10:43 am
1 stop7h 44m
Hartford Bradley Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$169
PortlandHartford
PDX Portland - BDL Hartford Bradley Intl
PDXBDL
Portland
Mon 10/19
11:30 pm-10:49 am
1 stop8h 19m
Hartford Bradley Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$169
PortlandHartford
PDX Portland - BDL Hartford Bradley Intl
PDXBDL
Portland
Wed 12/2
6:30 am-9:20 pm
2 stops11h 50m
Hartford Bradley Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$174
PortlandAlbany
PDX Portland - ALB Albany Intl
PDXALB
Portland
Thu 10/22
11:30 pm-10:39 am
1 stop8h 09m
Albany Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$182
PortlandAlbany
PDX Portland - ALB Albany Intl
PDXALB
Portland
Tue 10/20
7:02 am-5:42 pm
1 stop7h 40m
Albany Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$182
PortlandAlbany
PDX Portland - ALB Albany Intl
PDXALB
Portland
Mon 10/19
11:30 pm-10:39 am
1 stop8h 09m
Albany Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$182
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-BOS
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-ALB
PDX-BOS
PDX-PVC
What is the cheapest month to book a flight from Portland to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $327). Flying from Portland to Massachusetts in December is currently the most expensive (average of $529). 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 September 11, 2026.
It’s typically best to fly out from Portland to Massachusetts at noon. Doing so could potentially save you 31% on the flight price compared to flying in the morning, which is usually more expensive.
How much does it cost to fly round-trip from Portland to Massachusetts?
Airfare is typical for this route at the moment.
Portland to Massachusetts flights typically cost between $335 and $524 in October.The cheapest round-trip price found within the last 5 days was $335 on Alaska Airlines (Oct 17-Oct 24).
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 September 11, 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.
Entertainment
7.0
Comfort
7.8
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Related info for your journey
Find useful and relevant information for your journey from Portland to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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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 September 11, 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 7,457,451 searches. Data last updated September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$292 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$178 | Average$337 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$208 | Average$412 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$227 | Average$364 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$236 | Average$379 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$289 | Average$511 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$337 | Average$427 | FlexibilityNo cancel fee | On-time85% |