$122+ Cheap flights from Portland, ME (PWM) to Massachusetts
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Sep 4 — Sep 111
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 August 5, 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 August 5, 2026.
This JetBlue deal was found by Cheapflights users on 8/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:30 am -
1 stop4h 13m
Sat 10/316:40 pm -
1 stop5h 03m
Deal found 8/3![JetBlue logo]()
$243
This Priceline deal was found by Cheapflights users on 7/31. 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 9/42:45 pm -
1 stop4h 12m
Mon 9/78:25 am -
1 stop5h 21m
Deal found 7/31![JetBlue logo]()
$247
This JetBlue deal was found by Cheapflights users on 7/31. 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.
Mon 8/316:00 am -
1 stop5h 33m
Sun 9/67:41 am -
1 stop4h 49m
Deal found 7/31![JetBlue logo]()
$249
This Priceline deal was found by Cheapflights users on 8/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:30 am -
1 stop4h 13m
Fri 10/306:40 pm -
1 stop5h 03m
Deal found 8/3![JetBlue logo]()
$267
This Priceline deal was found by Cheapflights users on 8/1. 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.
Sat 8/222:40 pm -
1 stop4h 17m
Thu 9/37:05 pm -
1 stop5h 20m
Deal found 8/1![JetBlue logo]()
$281
This JetBlue deal was found by Cheapflights users on 8/4. 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 8/276:00 am -
1 stop5h 25m
Fri 8/288:09 pm -
1 stop4h 16m
Deal found 8/4![JetBlue logo]()
$289
This JetBlue deal was found by Cheapflights users on 7/31. 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.
Mon 8/246:00 am -
1 stop5h 33m
Mon 8/318:41 am -
1 stop5h 04m
Deal found 7/31![JetBlue logo]()
$314
This Justfly.com deal was found by Cheapflights users on 8/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:40 pm -
1 stop4h 44m
Wed 9/97:11 am -
1 stop16h 43m
Deal found 8/3![JetBlue logo]()
$338
This JetBlue deal was found by Cheapflights users on 7/31. 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 8/222:40 pm -
1 stop4h 17m
Fri 8/288:09 pm -
1 stop4h 16m
Deal found 7/31![JetBlue logo]()
$348
This Justfly.com deal was found by Cheapflights users on 8/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am -
1 stop4h 51m
Sun 10/47:00 pm -
1 stop4h 54m
Deal found 8/3![JetBlue logo]()
$353
This Southwest deal was found by Cheapflights users on 8/3. 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.
Wed 10/2812:55 pm -
1 stop4h 15m
Fri 10/3010:40 am -
1 stop6h 15m
Deal found 8/3![Southwest logo]()
$357
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 August 5, 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 August 5, 2026.
This JetBlue deal was found by Cheapflights users on 8/4. 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.
Fri 10/306:30 am -
1 stop4h 13m
Sat 10/316:40 pm -
1 stop5h 03m
Deal found 8/4![JetBlue logo]()
$243
This Southwest deal was found by Cheapflights users on 8/3. 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.
Wed 10/2812:55 pm -
1 stop4h 15m
Fri 10/3010:40 am -
1 stop6h 15m
Deal found 8/3![Southwest logo]()
$357
This Priceline deal was found by Cheapflights users on 7/31. 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 9/42:45 pm -
1 stop4h 12m
Mon 9/78:25 am -
1 stop5h 21m
Deal found 7/31![JetBlue logo]()
$247
This JetBlue deal was found by Cheapflights users on 7/31. 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.
Mon 8/316:00 am -
1 stop5h 33m
Sun 9/67:41 am -
1 stop4h 49m
Deal found 7/31![JetBlue logo]()
$249
This Southwest deal was found by Cheapflights users on 8/3. 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.
Mon 8/317:40 am -
1 stop7h 15m
Sun 9/67:45 am -
1 stop7h 45m
Deal found 8/3![Southwest logo]()
$377
This Priceline deal was found by Cheapflights users on 7/31. 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 8/306:00 am -
1 stop5h 33m
Sun 9/68:30 pm -
1 stop3h 55m
Deal found 7/31![JetBlue logo]()
$314
This JetBlue deal was found by Cheapflights users on 7/31. 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.
Mon 8/246:00 am -
1 stop5h 33m
Mon 8/318:41 am -
1 stop5h 04m
Deal found 7/31![JetBlue logo]()
$314
This Southwest deal was found by Cheapflights users on 8/2. 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.
Sun 8/307:40 am -
1 stop7h 45m
Sun 9/67:45 am -
1 stop7h 45m
Deal found 8/2![Southwest logo]()
$409
This JetBlue deal was found by Cheapflights users on 7/31. 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 8/222:40 pm -
1 stop4h 17m
Fri 8/288:09 pm -
1 stop4h 16m
Deal found 7/31![JetBlue logo]()
$348
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated August 5, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 8/1. 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.
Sat 8/222:40 pm -
1 stop4h 17m
Thu 9/37:05 pm -
1 stop5h 20m
Deal found 8/1![JetBlue logo]()
$281
This JetBlue deal was found by Cheapflights users on 7/31. 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 8/222:40 pm -
1 stop4h 17m
Fri 8/288:09 pm -
1 stop4h 16m
Deal found 7/31![JetBlue logo]()
$348
This JetBlue deal was found by Cheapflights users on 7/31. 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.
Mon 8/246:00 am -
1 stop5h 33m
Mon 8/318:41 am -
1 stop5h 04m
Deal found 7/31![JetBlue logo]()
$314
This JetBlue deal was found by Cheapflights users on 8/4. 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 8/276:00 am -
1 stop5h 25m
Fri 8/288:09 pm -
1 stop4h 16m
Deal found 8/4![JetBlue logo]()
$289
This Expedia deal was found by Cheapflights users on 8/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 am -
1 stop5h 33m
Sun 9/67:00 pm -
1 stop5h 25m
Deal found 8/2![JetBlue logo]()
$407
This JetBlue deal was found by Cheapflights users on 7/31. 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.
Mon 8/316:00 am -
1 stop5h 33m
Sun 9/67:41 am -
1 stop4h 49m
Deal found 7/31![JetBlue logo]()
$249
This Southwest deal was found by Cheapflights users on 8/3. 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.
Mon 8/317:40 am -
1 stop7h 15m
Sun 9/67:45 am -
1 stop7h 45m
Deal found 8/3![Southwest logo]()
$377
This JetBlue deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/11:20 pm -
1 stop6h 14m
Tue 9/86:05 am -
1 stop6h 25m
Deal found 8/4![JetBlue logo]()
$243
This Justfly.com deal was found by Cheapflights users on 8/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:40 pm -
1 stop4h 44m
Wed 9/97:11 am -
1 stop16h 43m
Deal found 8/3![JetBlue logo]()
$338
This Priceline deal was found by Cheapflights users on 7/31. 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 9/42:45 pm -
1 stop4h 12m
Mon 9/78:25 am -
1 stop5h 21m
Deal found 7/31![JetBlue logo]()
$247
This Justfly.com deal was found by Cheapflights users on 8/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am -
1 stop4h 51m
Sun 10/47:00 pm -
1 stop4h 54m
Deal found 8/3![JetBlue logo]()
$353
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 August 5, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
This JetBlue deal was found by Cheapflights users on 8/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 am -
1 stop4h 51m
Deal found 8/3![JetBlue logo]()
$122
This JetBlue deal was found by Cheapflights users on 8/2. 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.
Tue 9/11:20 pm -
1 stop4h 32m
Deal found 8/2![JetBlue logo]()
$124
This Priceline deal was found by Cheapflights users on 8/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am -
1 stop4h 46m
Deal found 8/3![JetBlue logo]()
$146
This Southwest deal was found by Cheapflights users on 8/1. 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.
Sat 11/215:25 pm -
1 stop3h 50m
Deal found 8/1![Southwest logo]()
$179
This Priceline deal was found by Cheapflights users on 7/31. 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 8/192:40 pm -
1 stop4h 17m
Deal found 7/31![JetBlue logo]()
$191
This Priceline deal was found by Cheapflights users on 8/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:40 pm -
1 stop4h 17m
Deal found 8/3![JetBlue logo]()
$194
This KAYAK deal was found by Cheapflights users on 8/4. 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 8/316:00 am -
1 stop5h 33m
Deal found 8/4![JetBlue logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 9/25:01 pm -
2 stops16h 08m
Deal found 8/2![Multiple Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Tue 9/18:00 am -
3 stops27h 47m
Deal found 8/2![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Sat 9/125:09 pm -
2 stops17h 49m
Deal found 8/2![Multiple Airlines logo]()
$230
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 August 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $243 (JetBlue) |
One-way from | $122 (JetBlue) |
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 2,558,603 searches. Data last updated August 5, 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 - BOS
PWMBOS
Portland
Fri 10/30
6:30 am-10:43 am
1 stop4h 13m
Boston Logan Intl
Sat 10/31
6:40 pm-11:43 pm
1 stop5h 03m
$243
PortlandBoston
PWM - BOS
PWMBOS
Portland
Fri 9/4
2:45 pm-6:57 pm
1 stop4h 12m
Boston Logan Intl
Mon 9/7
8:25 am-1:46 pm
1 stop5h 21m
$247
PortlandBoston
PWM - BOS
PWMBOS
Portland
Mon 8/31
6:00 am-11:33 am
1 stop5h 33m
Boston Logan Intl
Sun 9/6
7:41 am-12:30 pm
1 stop4h 49m
$249
PortlandBoston
PWM - BOS
PWMBOS
Portland
Sun 8/30
6:00 am-11:33 am
1 stop5h 33m
Boston Logan Intl
Sun 9/6
8:30 pm-12:25 am
1 stop3h 55m
$314
PortlandBoston
PWM - BOS
PWMBOS
Portland
Mon 8/24
6:00 am-11:33 am
1 stop5h 33m
Boston Logan Intl
Mon 8/31
8:41 am-1:45 pm
1 stop5h 04m
$314
Quickest round-trip
PortlandBoston
PWM - BOS
PWMBOS
Portland
Sat 8/22
2:40 pm-6:57 pm
1 stop4h 17m
Boston Logan Intl
Fri 8/28
8:09 pm-12:25 am
1 stop4h 16m
$348
PortlandBoston
PWM - BOS
PWMBOS
Portland
Wed 10/28
12:55 pm-5:10 pm
1 stop4h 15m
Boston Logan Intl
Fri 10/30
10:40 am-4:55 pm
1 stop6h 15m
$357
PortlandBoston
PWM - BOS
PWMBOS
Portland
Mon 8/31
7:40 am-2:55 pm
1 stop7h 15m
Boston Logan Intl
Sun 9/6
7:45 am-3:30 pm
1 stop7h 45m
$377
PortlandBoston
PWM - BOS
PWMBOS
Portland
Sun 8/30
7:40 am-3:25 pm
1 stop7h 45m
Boston Logan Intl
Sun 9/6
7:45 am-3:30 pm
1 stop7h 45m
$409
Cheapest one-way
PortlandBoston
PWM - BOS
PWMBOS
Portland
Tue 9/1
1:20 pm-5:52 pm
1 stop4h 32m
$124
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
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