$137+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Oct 13 — Oct 201
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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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 13, 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 13, 2026.
This JetBlue 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 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 9/9![JetBlue logo]()
$277
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 am -
1 stop5h 01m
Wed 10/146:40 pm -
1 stop5h 14m
Deal found 9/11![JetBlue logo]()
$288
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
1 stop4h 51m
Wed 10/76:40 pm -
1 stop5h 14m
Deal found 9/11![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 9/11. 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 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 10/106:35 pm -
1 stop5h 19m
Deal found 9/11![JetBlue logo]()
$297
This KAYAK 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 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 9/9![JetBlue logo]()
$309
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 am -
1 stop4h 51m
Wed 10/76:40 pm -
1 stop5h 14m
Deal found 9/11![JetBlue logo]()
$362
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:00 am -
1 stop4h 51m
Wed 10/76:40 pm -
1 stop5h 14m
Deal found 9/11![JetBlue logo]()
$363
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 11/215:25 pm -
1 stop6h 40m
Tue 12/15:30 am -
1 stop4h 20m
Deal found 9/10![Southwest logo]()
$367
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 13, 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 13, 2026.
This JetBlue 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 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 9/9![JetBlue logo]()
$277
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.
Sat 9/265:40 am -
1 stop4h 15m
Wed 9/303:20 pm -
1 stop6h 50m
Deal found 9/11![Southwest logo]()
$519
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:47 am -
1 stop8h 12m
Fri 10/97:00 am -
1 stop9h 57m
Deal found 9/11![American Airlines logo]()
$547
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.
Sat 10/312:05 pm -
1 stop9h 54m
Wed 11/45:30 am -
2 stops17h 51m
Deal found 9/9![United Airlines logo]()
$555
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 9/13. 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 JetBlue 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 JetBlue 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 10/154:11 pm -
1 stop7h 43m
Deal found 9/9![JetBlue logo]()
$392
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
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated September 13, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated September 13, 2026 and is based on user searches.
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am -
1 stop4h 51m
Mon 9/287:00 pm -
1 stop4h 54m
Deal found 9/9![JetBlue logo]()
$411
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:00 am -
1 stop4h 51m
Wed 10/76:40 pm -
1 stop5h 14m
Deal found 9/11![JetBlue logo]()
$363
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
1 stop4h 51m
Wed 10/76:40 pm -
1 stop5h 14m
Deal found 9/11![JetBlue logo]()
$295
This JetBlue 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 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 10/106:35 pm -
1 stop5h 19m
Deal found 9/11![JetBlue logo]()
$297
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 am -
1 stop4h 51m
Wed 10/76:40 pm -
1 stop5h 14m
Deal found 9/11![JetBlue logo]()
$362
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 am -
1 stop5h 01m
Wed 10/146:40 pm -
1 stop5h 14m
Deal found 9/11![JetBlue logo]()
$288
This JetBlue 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 JetBlue 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 10/154:11 pm -
1 stop7h 43m
Deal found 9/9![JetBlue logo]()
$392
This KAYAK 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 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 9/9![JetBlue logo]()
$309
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 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:30 am -
1 stop4h 11m
Wed 11/48:10 pm -
1 stop3h 33m
Deal found 9/9![JetBlue logo]()
$277
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 13, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
This KAYAK 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 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 9/10![JetBlue logo]()
$137
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:30 am -
1 stop4h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![JetBlue logo]()
$139
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 9/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:00 am -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![JetBlue logo]()
$147
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 am -
1 stop5h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![JetBlue logo]()
$149
This KAYAK 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 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![JetBlue logo]()
$171
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.
Wed 3/35:35 am -
1 stop6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$179
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 9/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am -
1 stop5h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![JetBlue logo]()
$204
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 KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:00 am -
1 stop4h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![JetBlue logo]()
$214
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
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 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $277 (JetBlue) |
One-way from | $137 (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 13, 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
Quickest round-trip
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Thu 11/5
6:30 am-10:41 am
1 stop4h 11m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
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
$147
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Tue 10/6
6:00 am-11:16 am
1 stop5h 16m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Wed 3/3
5:35 am-12:25 pm
1 stop6h 50m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
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
Sun 9/20
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
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
$277
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Mon 10/5
3:53 pm-12:07 pm
3 stops20h 14m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$292
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
Mon 10/19
3:53 pm-11:52 am
3 stops43h 59m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$305
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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