$184+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Oct 28 — Nov 41
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Massachusetts with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Portland to MassachusettsExplore the most affordable flight options available from Portland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 28, 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 28, 2026.
This American Airlines deal was found by Cheapflights users on 9/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:55 pm -
1 stop7h 42m
Thu 10/294:59 pm -
1 stop9h 06m
Deal found 9/25![American Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Thu 10/228:35 am -
1 stop10h 14m
Wed 10/287:00 am -
1 stop8h 22m
Deal found 9/27![American Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/1111:40 am -
1 stop9h 05m
Tue 11/171:10 pm -
2 stops12h 10m
Deal found 9/23![Southwest logo]()
$382
This Alaska Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/53:04 pm -
1 stop11h 42m
Tue 11/107:03 am -
1 stop12h 47m
Deal found 9/23![Alaska Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 9/25. 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 11/27:00 pm -
2 stops10h 20m
Tue 11/31:10 pm -
2 stops12h 05m
Deal found 9/25![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/71:40 pm -
2 stops15h 25m
Wed 11/115:55 pm -
1 stop8h 30m
Deal found 9/23![Southwest logo]()
$388
This American Airlines deal was found by Cheapflights users on 9/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:55 pm -
1 stop7h 42m
Thu 10/294:59 pm -
1 stop9h 06m
Deal found 9/25![American Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Fri 10/308:35 am -
1 stop7h 39m
Wed 11/41:30 pm -
1 stop9h 17m
Deal found 9/27![American Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/411:30 pm -
1 stop6h 53m
Sun 11/87:10 am -
1 stop10h 27m
Deal found 9/22![United Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 00m
Tue 10/274:20 pm -
1 stop9h 50m
Deal found 9/24![Southwest logo]()
$398
This SmartFares deal was found by Cheapflights users on 9/26. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:03 am -
Nonstop5h 27m
Tue 11/177:03 am -
1 stop12h 47m
Deal found 9/26![Alaska Airlines logo]()
$401
This Expedia deal was found by Cheapflights users on 9/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:44 pm -
1 stop11h 21m
Fri 10/164:30 pm -
2 stops10h 24m
Deal found 9/26![Multiple Airlines logo]()
$1,269
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 28, 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 28, 2026.
This Southwest deal was found by Cheapflights users on 9/27. 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.
Mon 10/267:35 pm -
2 stops10h 15m
Sat 10/317:20 am -
2 stops13h 45m
Deal found 9/27![Southwest logo]()
$403
This Alaska Airlines deal was found by Cheapflights users on 9/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:09 am -
1 stop19h 19m
Sat 10/317:51 am -
1 stop15h 49m
Deal found 9/25![Alaska Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 9/27. 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.
Thu 10/228:44 pm -
1 stop7h 51m
Mon 10/263:47 pm -
1 stop9h 09m
Deal found 9/27![Delta logo]()
$437
This Alaska Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/231:49 pm -
1 stop12h 32m
Tue 10/277:51 am -
1 stop12h 00m
Deal found 9/22![Alaska Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/2211:35 pm -
1 stop11h 50m
Thu 10/294:50 pm -
1 stop10h 25m
Deal found 9/24![Southwest logo]()
$432
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/1410:15 pm -
1 stop10h 00m
Sun 10/186:00 am -
1 stop8h 56m
Deal found 9/22![Delta logo]()
$437
This Alaska Airlines deal was found by Cheapflights users on 9/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:04 pm -
1 stop11h 42m
Mon 11/97:03 am -
1 stop16h 12m
Deal found 9/25![Alaska Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 3/26:04 am -
1 stop8h 44m
Wed 3/106:00 am -
1 stop9h 39m
Deal found 9/23![Delta logo]()
$437
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:35 pm -
1 stop7h 40m
Mon 10/2611:50 am -
2 stops11h 55m
Deal found 9/22![Southwest logo]()
$453
This Alaska Airlines deal was found by Cheapflights users on 9/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:04 pm -
1 stop11h 42m
Sat 11/77:03 pm -
Nonstop6h 23m
Deal found 9/25![Alaska Airlines logo]()
$451
This Alaska Airlines deal was found by Cheapflights users on 9/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/257:00 am -
Nonstop5h 27m
Mon 3/15:06 pm -
Nonstop6h 20m
Deal found 9/25![Alaska Airlines logo]()
$467
This Expedia deal was found by Cheapflights users on 9/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:44 pm -
1 stop11h 21m
Fri 10/164:30 pm -
2 stops10h 24m
Deal found 9/26![Multiple Airlines logo]()
$1,269
This Expedia deal was found by Cheapflights users on 9/25. 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.
Sat 10/109:44 pm -
1 stop8h 36m
Wed 10/1410:26 am -
2 stops16h 28m
Deal found 9/25![Multiple Airlines logo]()
$1,331
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated September 28, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated September 28, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/312:01 pm -
1 stop8h 33m
Sat 10/2412:00 pm -
1 stop10h 41m
Deal found 9/23![American Airlines logo]()
$532
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Mon 10/56:01 am -
1 stop10h 32m
Thu 10/1512:57 pm -
1 stop10h 47m
Deal found 9/27![American Airlines logo]()
$582
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/62:20 pm -
1 stop8h 00m
Thu 10/155:39 am -
1 stop8h 02m
Deal found 9/23![Delta logo]()
$572
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/711:43 am -
1 stop9h 16m
Wed 10/143:47 pm -
1 stop9h 09m
Deal found 9/23![Delta logo]()
$467
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/78:35 am -
1 stop10h 14m
Wed 10/143:06 pm -
1 stop10h 59m
Deal found 9/23![American Airlines logo]()
$468
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/712:29 pm -
1 stop8h 29m
Thu 10/153:47 pm -
1 stop9h 09m
Deal found 9/23![Delta logo]()
$492
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/710:54 am -
1 stop10h 00m
Sat 10/106:00 am -
1 stop8h 56m
Deal found 9/23![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/75:15 pm -
1 stop9h 12m
Tue 10/135:50 am -
1 stop7h 44m
Deal found 9/23![Delta logo]()
$528
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/72:27 pm -
1 stop7h 27m
Wed 10/149:51 am -
2 stops13h 19m
Deal found 9/22![United Airlines logo]()
$562
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/711:25 am -
1 stop9h 33m
Sun 10/116:50 am -
1 stop9h 48m
Deal found 9/24![Delta logo]()
$568
This Expedia deal was found by Cheapflights users on 9/25. 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.
Sat 10/109:44 pm -
1 stop8h 36m
Wed 10/1410:26 am -
2 stops16h 28m
Deal found 9/25![Multiple Airlines logo]()
$1,331
This Expedia deal was found by Cheapflights users on 9/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:44 pm -
1 stop11h 21m
Fri 10/164:30 pm -
2 stops10h 24m
Deal found 9/26![Multiple Airlines logo]()
$1,269
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 28, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/27:00 am -
1 stop11h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![United Airlines logo]()
$184
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/39:00 am -
1 stop7h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![United Airlines logo]()
$189
This Alaska Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/242:53 pm -
1 stop11h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Alaska Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Southwest logo]()
$194
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Thu 10/228:35 am -
1 stop10h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$196
This Alaska Airlines deal was found by Cheapflights users on 9/27. 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.
Sat 10/171:49 pm -
1 stop12h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Alaska Airlines logo]()
$197
This United Airlines deal was found by Cheapflights users on 9/25. 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 11/137:00 am -
1 stop11h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![United Airlines logo]()
$200
This Alaska Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/272:53 pm -
1 stop11h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Alaska Airlines logo]()
$202
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 3/237:10 am -
1 stop10h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![United Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/238:35 am -
1 stop10h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![American Airlines logo]()
$205
This Alaska Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 12/39:00 am -
1 stop29h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Alaska Airlines logo]()
$207
This United Airlines deal was found by Cheapflights users on 9/25. 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.
Sun 10/2511:33 pm -
1 stop7h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![United Airlines logo]()
$209
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 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $376 (American Airlines) |
One-way from | $184 (United Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $424 |
Good round-trip deal | $482 or less |
Good one-way deal | $233 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 28, 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 Portland - BOS Boston Logan Intl
PDXBOS
Portland
Mon 2/15
10:56 pm-10:39 am
1 stop8h 43m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$189
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sat 10/31
6:20 am-7:25 pm
2 stops10h 05m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$210
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sat 10/24
7:05 pm-9:55 am
2 stops11h 50m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$210
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Fri 11/13
7:00 pm-8:10 am
2 stops10h 10m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$210
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Fri 10/30
11:35 pm-12:30 pm
2 stops9h 55m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$210
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Fri 12/4
6:00 am-6:58 pm
1 stop9h 58m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$219
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sat 10/31
7:03 am-3:43 pm
Nonstop5h 40m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$234
Quickest round-trip
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Fri 11/27
7:04 am-3:25 pm
Nonstop5h 21m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$234
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Mon 1/11
7:27 am-3:53 pm
Nonstop5h 26m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$234
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sat 11/21
9:59 pm-6:20 am
Nonstop5h 21m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$234
Showing 1-10 of 24 resultsSorted by cheapest first
Best time to book a flight from Portland to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Portland with our price prediction graph.
PDX-BOS
PDX-MVY
PDX-HYA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Massachusetts
PDX-USMA
PDX-BOS
PDX-MVY
PDX-HYA
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 $530). 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 28, 2026.
It’s typically best to fly out from Portland to Massachusetts at noon. Doing so could potentially save you 32% 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 September 28, 2026.
The most flights from PDX to USMA are scheduled on a Sunday (4 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).
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 $374 and $631 in October.The cheapest round-trip price found within the last 5 days was $376 on American Airlines (Oct 22-Oct 29).
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 28, 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
Food
7.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Food
7.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Food
7.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Food
7.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Food
7.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Food
7.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
7.9
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
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 September 28, 2026.
Popular flight searches
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Portland to Massachusetts flights
Consider these flights traveling from Portland to Massachusetts.
Top 6 airlines flying from Portland to Massachusetts
Discover the top 6 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 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$115 | Average$291 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$178 | Average$341 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$208 | Average$399 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$227 | Average$364 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$236 | Average$382 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$288 | Average$514 | FlexibilityNo cancel fee | On-time75% |