$129+ Cheap flights from Portland, ME (PWM) 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Nov 24 — Dec 11
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 October 25, 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 October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/235:10 pm -
1 stop6h 45m
Tue 12/13:30 pm -
1 stop6h 20m
Deal found 10/20![Southwest logo]()
$258
This JetBlue deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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.
Tue 11/106:30 am -
1 stop4h 11m
Wed 11/116:39 pm -
1 stop5h 04m
Deal found 10/20![JetBlue logo]()
$297
This Southwest deal was found by Cheapflights users on 10/22. 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.
Thu 11/195:15 am -
1 stop5h 20m
Thu 11/265:25 am -
1 stop5h 05m
Deal found 10/22![Southwest logo]()
$360
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/195:25 pm -
1 stop6h 45m
Sun 1/35:25 am -
1 stop4h 25m
Deal found 10/20![Southwest logo]()
$378
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/55:25 am -
1 stop7h 25m
Sun 12/135:35 am -
1 stop4h 55m
Deal found 10/21![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/1710:25 am -
1 stop4h 05m
Tue 11/245:25 am -
1 stop4h 25m
Deal found 10/20![Southwest logo]()
$400
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/51:40 pm -
1 stop6h 15m
Mon 11/95:35 am -
1 stop4h 55m
Deal found 10/21![Southwest logo]()
$411
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/205:20 am -
1 stop4h 20m
Fri 11/275:35 am -
1 stop4h 55m
Deal found 10/21![Southwest logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Sat 12/512:28 pm -
2 stops21h 13m
Sun 12/1311:08 am -
1 stop22h 00m
Deal found 10/21![Multiple Airlines logo]()
$436
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 October 25, 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 October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/23. 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 12/1412:45 pm -
1 stop6h 00m
Thu 12/175:35 am -
1 stop4h 55m
Deal found 10/23![Southwest logo]()
$258
This JetBlue deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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.
Tue 11/106:30 am -
1 stop4h 11m
Wed 11/116:39 pm -
1 stop5h 04m
Deal found 10/20![JetBlue logo]()
$297
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/194:30 pm -
1 stop15h 51m
Wed 1/68:45 pm -
1 stop17h 08m
Deal found 10/20![Delta logo]()
$505
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/235:10 pm -
1 stop6h 45m
Tue 12/13:30 pm -
1 stop6h 20m
Deal found 10/20![Southwest logo]()
$258
This Priceline deal was found by Cheapflights users on 10/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:30 am -
1 stop8h 30m
Thu 11/124:09 pm -
1 stop7h 34m
Deal found 10/24![JetBlue logo]()
$431
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/51:40 pm -
1 stop6h 15m
Mon 11/95:35 am -
1 stop4h 55m
Deal found 10/21![Southwest logo]()
$411
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/205:20 am -
1 stop4h 20m
Fri 11/275:35 am -
1 stop4h 55m
Deal found 10/21![Southwest logo]()
$422
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/196:35 am -
1 stop25h 46m
Mon 1/41:10 pm -
1 stop24h 43m
Deal found 10/20![Delta logo]()
$542
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/196:35 am -
1 stop25h 46m
Sat 1/212:00 pm -
1 stop11h 06m
Deal found 10/20![Delta logo]()
$575
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated October 25, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/51:40 pm -
1 stop6h 15m
Mon 11/95:35 am -
1 stop4h 55m
Deal found 10/21![Southwest logo]()
$411
This JetBlue deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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.
Tue 11/106:30 am -
1 stop4h 11m
Wed 11/116:39 pm -
1 stop5h 04m
Deal found 10/20![JetBlue logo]()
$297
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/1710:25 am -
1 stop4h 05m
Tue 11/245:25 am -
1 stop4h 25m
Deal found 10/20![Southwest logo]()
$400
This Southwest deal was found by Cheapflights users on 10/22. 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.
Thu 11/195:15 am -
1 stop5h 20m
Thu 11/265:25 am -
1 stop5h 05m
Deal found 10/22![Southwest logo]()
$360
This United Airlines deal was found by Cheapflights users on 10/22. 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.
Thu 11/195:50 am -
2 stops18h 09m
Thu 11/265:30 am -
1 stop8h 57m
Deal found 10/22![United Airlines logo]()
$648
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/205:20 am -
1 stop4h 20m
Fri 11/275:35 am -
1 stop4h 55m
Deal found 10/21![Southwest logo]()
$422
This Southwest deal was found by Cheapflights users on 10/23. 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 11/215:25 pm -
1 stop6h 45m
Sat 11/285:40 am -
1 stop3h 45m
Deal found 10/23![Southwest logo]()
$558
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/235:10 pm -
1 stop6h 45m
Tue 12/13:30 pm -
1 stop6h 20m
Deal found 10/20![Southwest logo]()
$258
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 October 25, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/155:15 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$129
This Southwest deal was found by Cheapflights users on 10/22. 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.
Sat 3/64:00 pm -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/710:54 am -
1 stop22h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$261
This Priceline deal was found by Cheapflights users on 10/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:30 am -
1 stop4h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![JetBlue logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/66:31 pm -
3 stops38h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 10/22. 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.
Fri 3/55:59 pm -
1 stop22h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$318
This Priceline deal was found by Cheapflights users on 10/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:30 am -
1 stop4h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![JetBlue logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:31 pm -
2 stops17h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 10/22. 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.
Sun 3/75:59 pm -
2 stops13h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$406
This United Airlines deal was found by Cheapflights users on 10/22. 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.
Sat 11/286:00 am -
1 stop25h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![United Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/159:12 am -
2 stops10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![United Airlines logo]()
$413
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 October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $258 (Southwest) |
One-way from | $129 (Southwest) |
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 October 25, 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
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Tue 12/15
5:15 am-12:20 pm
1 stop7h 05m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Sat 3/6
4:00 pm-11:20 pm
1 stop7h 20m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Mon 12/14
12:45 pm-6:45 pm
1 stop6h 00m
Boston Logan Intl
Thu 12/17
5:35 am-10:30 am
1 stop4h 55m
$258
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Mon 11/23
5:10 pm-11:55 pm
1 stop6h 45m
Boston Logan Intl
Tue 12/1
3:30 pm-9:50 pm
1 stop6h 20m
$258
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Sun 3/7
10:54 am-9:26 am
1 stop22h 32m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$261
Quickest round-trip
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Wed 11/4
6:30 am-10:41 am
1 stop4h 11m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$270
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Tue 11/10
6:30 am-10:41 am
1 stop4h 11m
Boston Logan Intl
Wed 11/11
6:39 pm-11:43 pm
1 stop5h 04m
$297
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Fri 3/5
5:59 pm-4:23 pm
1 stop22h 24m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$318
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Fri 10/30
6:30 am-10:41 am
1 stop4h 11m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$319
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Wed 11/4
6:31 pm-11:44 am
2 stops17h 13m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$352
Showing 1-10 of 21 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.
PWM-BOS
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
PWM-USMA
PWM-BOS
No data available for this route at this time. Please check back soon.
Related info for your journey
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