$149+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Nov 13 — Nov 201
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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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 October 14, 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 14, 2026.
This flygcity.se deal was found by Cheapflights users on 10/13. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:30 am -
1 stop4h 11m
Thu 11/128:10 pm -
1 stop3h 33m
Deal found 10/13![JetBlue logo]()
$279
This JetBlue deal was found by Cheapflights users on 10/9. 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 10/9![JetBlue logo]()
$297
This JetBlue deal was found by Cheapflights users on 10/11. 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.
Sun 11/16:30 am -
1 stop4h 11m
Sat 11/79:42 am -
1 stop14h 01m
Deal found 10/11![JetBlue logo]()
$370
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:20 am -
1 stop4h 20m
Mon 11/169:10 am -
1 stop5h 35m
Deal found 10/10![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 10/10. 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.
Wed 12/235:20 pm -
1 stop4h 00m
Mon 12/285:25 am -
1 stop4h 25m
Deal found 10/10![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2410:25 am -
1 stop5h 25m
Sat 1/25:40 am -
1 stop3h 45m
Deal found 10/13![Southwest logo]()
$427
This Priceline deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop4h 51m
Tue 10/278:10 pm -
1 stop3h 33m
Deal found 10/10![JetBlue logo]()
$431
This Southwest deal was found by Cheapflights users on 10/11. 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.
Tue 11/245:25 am -
1 stop6h 30m
Sat 11/285:40 am -
1 stop3h 45m
Deal found 10/11![Southwest logo]()
$514
This Priceline deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:00 am -
1 stop5h 01m
Sun 10/258:10 pm -
1 stop3h 33m
Deal found 10/10![JetBlue logo]()
$534
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:25 am -
1 stop5h 55m
Thu 12/317:55 am -
1 stop6h 50m
Deal found 10/13![Southwest logo]()
$557
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:41 pm -
2 stops18h 38m
Tue 11/175:30 am -
1 stop8h 57m
Deal found 10/13![United Airlines logo]()
$568
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 14, 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 14, 2026.
This flygcity.se deal was found by Cheapflights users on 10/13. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:30 am -
1 stop4h 11m
Thu 11/128:10 pm -
1 stop3h 33m
Deal found 10/13![JetBlue logo]()
$279
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2410:25 am -
1 stop5h 25m
Sat 1/25:40 am -
1 stop3h 45m
Deal found 10/13![Southwest logo]()
$427
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:41 pm -
2 stops18h 38m
Tue 11/175:30 am -
1 stop8h 57m
Deal found 10/13![United Airlines logo]()
$568
This JetBlue deal was found by Cheapflights users on 10/10. 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 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 10/10![JetBlue logo]()
$297
This Expedia deal was found by Cheapflights users on 10/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:30 am -
1 stop10h 29m
Wed 11/188:10 pm -
1 stop3h 33m
Deal found 10/14![JetBlue logo]()
$297
This Priceline deal was found by Cheapflights users on 10/9. 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.
Sun 11/86:30 am -
1 stop4h 11m
Sun 11/156:39 pm -
1 stop5h 04m
Deal found 10/9![JetBlue logo]()
$364
This JetBlue deal was found by Cheapflights users on 10/11. 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.
Sun 11/16:30 am -
1 stop4h 11m
Sat 11/79:42 am -
1 stop14h 01m
Deal found 10/11![JetBlue logo]()
$370
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:25 am -
1 stop5h 55m
Thu 12/317:55 am -
1 stop6h 50m
Deal found 10/13![Southwest logo]()
$557
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated October 14, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:00 am -
1 stop5h 01m
Sun 10/258:10 pm -
1 stop3h 33m
Deal found 10/10![JetBlue logo]()
$534
This Priceline deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop4h 51m
Tue 10/278:10 pm -
1 stop3h 33m
Deal found 10/10![JetBlue logo]()
$431
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:25 am -
1 stop5h 55m
Thu 12/317:55 am -
1 stop6h 50m
Deal found 10/13![Southwest logo]()
$557
This JetBlue deal was found by Cheapflights users on 10/9. 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 10/9![JetBlue logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/9. 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 10/315:30 am -
1 stop13h 27m
Wed 11/45:30 am -
2 stops17h 51m
Deal found 10/9![United Airlines logo]()
$606
This JetBlue deal was found by Cheapflights users on 10/11. 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.
Sun 11/16:30 am -
1 stop4h 11m
Sat 11/79:42 am -
1 stop14h 01m
Deal found 10/11![JetBlue logo]()
$370
This flygcity.se deal was found by Cheapflights users on 10/13. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:30 am -
1 stop4h 11m
Thu 11/128:10 pm -
1 stop3h 33m
Deal found 10/13![JetBlue logo]()
$279
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:20 am -
1 stop4h 20m
Mon 11/169:10 am -
1 stop5h 35m
Deal found 10/10![Southwest logo]()
$377
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:41 pm -
2 stops18h 38m
Tue 11/175:30 am -
1 stop8h 57m
Deal found 10/13![United Airlines logo]()
$568
This Southwest deal was found by Cheapflights users on 10/11. 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.
Tue 11/245:25 am -
1 stop6h 30m
Sat 11/285:40 am -
1 stop3h 45m
Deal found 10/11![Southwest logo]()
$514
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 14, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
This Priceline deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:30 am -
1 stop4h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![JetBlue logo]()
$149
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:25 am -
1 stop4h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Southwest logo]()
$189
This Priceline deal was found by Cheapflights users on 10/12. 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 Priceline 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 10/12![JetBlue logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:28 pm -
2 stops21h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:53 pm -
3 stops17h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/123:10 pm -
3 stops42h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 10/14. 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.
Fri 11/275:20 am -
1 stop4h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Southwest logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:31 pm -
3 stops39h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Thu 10/293:10 pm -
3 stops42h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$303
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Fri 11/278:49 am -
2 stops15h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$349
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 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $279 (flygcity.se) |
One-way from | $149 (Priceline) |
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 14, 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
Sat 11/7
6:30 am-10:46 am
1 stop4h 16m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
Quickest round-trip
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Thu 11/12
6:30 am-10:41 am
1 stop4h 11m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Mon 12/21
5:20 pm-10:50 pm
1 stop5h 30m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Sat 12/12
5:25 am-10:05 am
1 stop4h 40m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Sat 12/12
12:28 pm-10:13 am
2 stops21h 45m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$230
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Thu 11/12
3:10 pm-9:29 am
3 stops42h 19m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$257
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Fri 11/27
5:20 am-9:40 am
1 stop4h 20m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$259
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Fri 11/6
6:30 am-10:41 am
1 stop4h 11m
Boston Logan Intl
Thu 11/12
8:10 pm-11:43 pm
1 stop3h 33m
$279
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
Wed 11/11
6:30 am-4:59 pm
1 stop10h 29m
Boston Logan Intl
Wed 11/18
8:10 pm-11:43 pm
1 stop3h 33m
$297
Showing 1-10 of 19 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
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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