$145+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Massachusetts
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Last-minute
One-way
Cheapest flights from Portland to MassachusettsExplore the most affordable flight options available from Portland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 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 17, 2026.
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 am -
1 stop5h 01m
Sat 10/108:11 pm -
1 stop3h 43m
Deal found 9/14![JetBlue logo]()
$295
This Expedia deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
Wed 10/286:30 am -
1 stop4h 11m
Wed 11/48:10 pm -
1 stop3h 33m
Deal found 9/13![JetBlue logo]()
$296
This JetBlue deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:30 am -
1 stop4h 11m
Wed 11/48:10 pm -
1 stop3h 33m
Deal found 9/16![JetBlue logo]()
$297
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/75:25 am -
1 stop7h 25m
Sat 11/147:25 am -
1 stop7h 20m
Deal found 9/14![Southwest logo]()
$312
This KAYAK deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Mon 10/196:00 am -
1 stop5h 01m
Thu 10/226:40 pm -
1 stop5h 14m
Deal found 9/15![JetBlue logo]()
$329
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 12/410:25 am -
1 stop5h 25m
Sun 12/135:10 pm -
1 stop6h 40m
Deal found 9/15![Southwest logo]()
$344
This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
1 stop4h 51m
Sat 10/108:11 pm -
1 stop3h 43m
Deal found 9/13![JetBlue logo]()
$364
This KAYAK deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/26:00 am -
1 stop4h 51m
Tue 10/66:10 pm -
1 stop5h 44m
Deal found 9/13![JetBlue logo]()
$416
This KAYAK deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/306:30 am -
1 stop4h 11m
Sun 11/14:10 pm -
1 stop7h 33m
Deal found 9/12![JetBlue logo]()
$420
This Expedia deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/106:00 am -
1 stop8h 29m
Sat 10/178:11 pm -
1 stop3h 43m
Deal found 9/12![JetBlue logo]()
$421
This Priceline deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/146:00 am -
1 stop8h 29m
Wed 10/216:39 pm -
1 stop5h 15m
Deal found 9/15![JetBlue logo]()
$422
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 17, 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 17, 2026.
This Expedia deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
Wed 10/286:30 am -
1 stop4h 11m
Wed 11/48:10 pm -
1 stop3h 33m
Deal found 9/13![JetBlue logo]()
$296
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 12/410:25 am -
1 stop5h 25m
Sun 12/135:10 pm -
1 stop6h 40m
Deal found 9/15![Southwest logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Fri 12/49:48 am -
1 stop25h 14m
Sun 12/1311:35 am -
2 stops46h 39m
Deal found 9/15![Multiple Airlines logo]()
$530
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/319:46 am -
1 stop14h 13m
Wed 11/45:30 am -
2 stops17h 51m
Deal found 9/14![United Airlines logo]()
$550
This JetBlue deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:30 am -
1 stop4h 11m
Wed 11/48:10 pm -
1 stop3h 33m
Deal found 9/15![JetBlue logo]()
$297
This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
1 stop4h 51m
Sat 10/108:11 pm -
1 stop3h 43m
Deal found 9/13![JetBlue logo]()
$364
This KAYAK deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
Mon 10/126:00 am -
1 stop5h 01m
Mon 10/196:40 pm -
1 stop5h 14m
Deal found 9/12![JetBlue logo]()
$416
This KAYAK deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/26:00 am -
1 stop4h 51m
Tue 10/66:10 pm -
1 stop5h 44m
Deal found 9/13![JetBlue logo]()
$416
This KAYAK deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/306:30 am -
1 stop4h 11m
Sun 11/14:10 pm -
1 stop7h 33m
Deal found 9/12![JetBlue logo]()
$420
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated September 17, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
Mon 9/286:00 am -
1 stop4h 51m
Fri 10/26:59 pm -
1 stop4h 55m
Deal found 9/13![JetBlue logo]()
$431
This KAYAK deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/26:00 am -
1 stop4h 51m
Tue 10/66:10 pm -
1 stop5h 44m
Deal found 9/13![JetBlue logo]()
$416
This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
1 stop4h 51m
Sat 10/108:11 pm -
1 stop3h 43m
Deal found 9/13![JetBlue logo]()
$364
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 am -
1 stop5h 01m
Sat 10/108:11 pm -
1 stop3h 43m
Deal found 9/14![JetBlue logo]()
$295
This lol.travel deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
Thu 10/86:00 am -
1 stop5h 01m
Thu 10/156:40 pm -
1 stop5h 14m
Deal found 9/13![JetBlue logo]()
$425
This Expedia deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/106:00 am -
1 stop8h 29m
Sat 10/178:11 pm -
1 stop3h 43m
Deal found 9/12![JetBlue logo]()
$421
This Priceline deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/146:00 am -
1 stop8h 29m
Wed 10/216:39 pm -
1 stop5h 15m
Deal found 9/15![JetBlue logo]()
$422
This KAYAK deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Mon 10/196:00 am -
1 stop5h 01m
Thu 10/226:40 pm -
1 stop5h 14m
Deal found 9/15![JetBlue logo]()
$329
This Expedia deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
Wed 10/286:30 am -
1 stop4h 11m
Wed 11/48:10 pm -
1 stop3h 33m
Deal found 9/13![JetBlue logo]()
$296
This KAYAK deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/306:30 am -
1 stop4h 11m
Sun 11/14:10 pm -
1 stop7h 33m
Deal found 9/12![JetBlue logo]()
$420
This JetBlue deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:30 am -
1 stop4h 11m
Wed 11/48:10 pm -
1 stop3h 33m
Deal found 9/16![JetBlue logo]()
$297
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 17, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This KAYAK deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
Sat 11/146:30 am -
1 stop4h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![JetBlue logo]()
$145
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Tue 10/136:00 am -
1 stop4h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![JetBlue logo]()
$147
This Expedia deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Thu 10/296:30 am -
1 stop3h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![JetBlue logo]()
$149
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 12/83:25 pm -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Southwest logo]()
$189
This KAYAK deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
Sun 10/116:00 am -
1 stop5h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![JetBlue logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates ” 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 11/146:31 pm -
2 stops39h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$251
This KAYAK deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
Mon 10/126:00 am -
1 stop5h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![JetBlue logo]()
$264
This KAYAK deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Sat 9/266:00 am -
1 stop4h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![JetBlue logo]()
$267
This KAYAK deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
Sun 9/206:00 am -
1 stop4h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![JetBlue logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
Tue 12/810:01 am -
3 stops47h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Tue 9/225:09 pm -
2 stops19h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$345
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 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $295 (KAYAK) |
One-way from | $145 (KAYAK) |
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 17, 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 12/8
3:25 pm-9:50 pm
1 stop6h 25m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Mon 10/5
6:00 am-11:49 am
1 stop5h 49m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$216
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Sat 11/14
6:31 pm-9:41 am
2 stops39h 10m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$251
Quickest round-trip
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Tue 9/22
6:00 am-10:51 am
1 stop4h 51m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$268
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Wed 10/28
6:30 am-10:41 am
1 stop4h 11m
Boston Logan Intl
Wed 11/4
8:10 pm-11:43 pm
1 stop3h 33m
$296
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Sat 10/31
6:30 am-10:41 am
1 stop4h 11m
Boston Logan Intl
Wed 11/4
8:10 pm-11:43 pm
1 stop3h 33m
$297
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Fri 12/4
10:25 am-3:50 pm
1 stop5h 25m
Boston Logan Intl
Sun 12/13
5:10 pm-11:50 pm
1 stop6h 40m
$344
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Fri 9/25
3:53 pm-10:51 am
3 stops18h 58m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$348
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Tue 10/20
5:09 pm-11:02 am
3 stops41h 53m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$352
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Fri 9/25
3:40 pm-10:15 pm
1 stop6h 35m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$353
Showing 1-10 of 20 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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