$139+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Oct 6 — Oct 131
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 6, 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 6, 2026.
This KAYAK deal was found by Cheapflights users on 9/5. 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 9/5![JetBlue logo]()
$276
This JetBlue deal was found by Cheapflights users on 9/2. 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 9/2![JetBlue logo]()
$277
This JetBlue deal was found by Cheapflights users on 9/2. 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 9/276:00 am -
1 stop4h 51m
Sat 10/36:40 pm -
1 stop5h 14m
Deal found 9/2![JetBlue logo]()
$278
This Priceline deal was found by Cheapflights users on 9/1. 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 11/56:30 am -
1 stop4h 11m
Sun 11/86:39 pm -
1 stop5h 04m
Deal found 9/1![JetBlue logo]()
$344
This Southwest deal was found by Cheapflights users on 9/1. 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 11/55:10 pm -
1 stop5h 20m
Sat 11/77:25 am -
1 stop7h 20m
Deal found 9/1![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 9/3. 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 11/205:10 pm -
1 stop5h 20m
Fri 11/275:35 am -
1 stop4h 55m
Deal found 9/3![Southwest logo]()
$377
This FlightHub deal was found by Cheapflights users on 9/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:00 am -
1 stop11h 21m
Tue 9/296:40 pm -
1 stop5h 14m
Deal found 9/3![JetBlue logo]()
$388
This Priceline deal was found by Cheapflights users on 9/1. 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 9/136:00 am -
1 stop4h 51m
Tue 9/226:40 pm -
1 stop5h 14m
Deal found 9/1![JetBlue logo]()
$398
This Priceline deal was found by Cheapflights users on 9/2. 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 9/166:00 am -
1 stop4h 51m
Sat 9/196:40 pm -
1 stop5h 14m
Deal found 9/2![JetBlue logo]()
$411
This Southwest deal was found by Cheapflights users on 9/2. 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 9/302:50 pm -
1 stop6h 40m
Wed 10/73:50 pm -
1 stop6h 50m
Deal found 9/2![Southwest logo]()
$428
This Southwest deal was found by Cheapflights users on 9/2. 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 11/265:15 am -
1 stop7h 00m
Mon 11/305:25 am -
1 stop4h 25m
Deal found 9/2![Southwest logo]()
$439
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 6, 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 6, 2026.
This JetBlue deal was found by Cheapflights users on 9/5. 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 9/5![JetBlue logo]()
$277
This Southwest deal was found by Cheapflights users on 9/1. 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 11/55:10 pm -
1 stop5h 20m
Sat 11/77:25 am -
1 stop7h 20m
Deal found 9/1![Southwest logo]()
$357
This JetBlue deal was found by Cheapflights users on 9/5. 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 9/5![JetBlue logo]()
$277
This JetBlue deal was found by Cheapflights users on 9/2. 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 9/276:00 am -
1 stop4h 51m
Sat 10/36:40 pm -
1 stop5h 14m
Deal found 9/2![JetBlue logo]()
$278
This Priceline deal was found by Cheapflights users on 9/1. 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 11/56:30 am -
1 stop4h 11m
Sun 11/86:39 pm -
1 stop5h 04m
Deal found 9/1![JetBlue logo]()
$344
This Southwest deal was found by Cheapflights users on 9/2. 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 9/302:50 pm -
1 stop6h 40m
Wed 10/73:50 pm -
1 stop6h 50m
Deal found 9/2![Southwest logo]()
$428
This Southwest deal was found by Cheapflights users on 9/5. 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 10/312:45 pm -
1 stop5h 35m
Sat 10/105:40 pm -
1 stop4h 35m
Deal found 9/5![Southwest logo]()
$514
This KAYAK deal was found by Cheapflights users on 9/5. 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 9/246:00 am -
1 stop4h 51m
Sat 9/266:40 pm -
1 stop5h 14m
Deal found 9/5![JetBlue logo]()
$464
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated September 6, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated September 6, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 9/1. 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 9/136:00 am -
1 stop4h 51m
Tue 9/226:40 pm -
1 stop5h 14m
Deal found 9/1![JetBlue logo]()
$398
This Priceline deal was found by Cheapflights users on 9/1. 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 9/136:00 am -
1 stop4h 51m
Wed 9/166:40 pm -
1 stop5h 14m
Deal found 9/1![JetBlue logo]()
$465
This Priceline deal was found by Cheapflights users on 9/2. 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 9/166:00 am -
1 stop4h 51m
Sat 9/196:40 pm -
1 stop5h 14m
Deal found 9/2![JetBlue logo]()
$411
This KAYAK deal was found by Cheapflights users on 9/3. 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 9/236:40 pm -
1 stop5h 14m
Deal found 9/3![JetBlue logo]()
$464
This FlightHub deal was found by Cheapflights users on 9/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am -
1 stop25h 59m
Sat 9/266:40 pm -
1 stop5h 14m
Deal found 9/3![JetBlue logo]()
$455
This FlightHub deal was found by Cheapflights users on 9/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:00 am -
1 stop11h 21m
Tue 9/296:40 pm -
1 stop5h 14m
Deal found 9/3![JetBlue logo]()
$388
This JetBlue deal was found by Cheapflights users on 9/2. 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 9/276:00 am -
1 stop4h 51m
Sat 10/36:40 pm -
1 stop5h 14m
Deal found 9/2![JetBlue logo]()
$278
This Southwest deal was found by Cheapflights users on 9/2. 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 9/302:50 pm -
1 stop6h 40m
Wed 10/73:50 pm -
1 stop6h 50m
Deal found 9/2![Southwest logo]()
$428
This Justfly.com deal was found by Cheapflights users on 9/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:00 am -
1 stop25h 59m
Fri 10/96:55 am -
1 stop16h 59m
Deal found 9/2![JetBlue logo]()
$489
This KAYAK deal was found by Cheapflights users on 9/5. 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 9/5![JetBlue logo]()
$276
This JetBlue deal was found by Cheapflights users on 9/2. 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 9/2![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 6, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
This Priceline deal was found by Cheapflights users on 9/2. 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 9/236:00 am -
1 stop4h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![JetBlue logo]()
$139
This Southwest deal was found by Cheapflights users on 9/1. 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 11/55:10 pm -
1 stop6h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Southwest logo]()
$179
This KAYAK deal was found by Cheapflights users on 9/3. 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 9/3![JetBlue logo]()
$205
This Priceline deal was found by Cheapflights users on 9/2. 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![JetBlue logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Mon 9/283:53 pm -
3 stops20h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 9/237:00 am -
3 stops27h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 10/127:00 am -
2 stops28h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$321
This United Airlines deal was found by Cheapflights users on 9/1. 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 11/53:41 pm -
2 stops18h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![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 September 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $276 (KAYAK) |
One-way from | $139 (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 September 6, 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
Wed 9/23
6:00 am-10:51 am
1 stop4h 51m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Thu 11/5
5:10 pm-11:50 pm
1 stop6h 40m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Mon 10/12
6:00 am-11:01 am
1 stop5h 01m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$205
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Mon 9/28
6:00 am-10:51 am
1 stop4h 51m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$206
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
Sat 10/3
6:00 am-10:51 am
1 stop4h 51m
Boston Logan Intl
Sat 10/10
6:35 pm-11:54 pm
1 stop5h 19m
$277
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Sun 9/27
6:00 am-10:51 am
1 stop4h 51m
Boston Logan Intl
Sat 10/3
6:40 pm-11:54 pm
1 stop5h 14m
$278
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Wed 9/23
7:00 am-10:22 am
3 stops27h 22m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Mon 10/12
7:00 am-11:52 am
2 stops28h 52m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$321
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Thu 11/5
6:30 am-10:41 am
1 stop4h 11m
Boston Logan Intl
Sun 11/8
6:39 pm-11:43 pm
1 stop5h 04m
$344
Showing 1-10 of 14 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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