$170+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Nov 29 — Dec 61
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to MassachusettsExplore the most affordable flight options available from Portland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 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 30, 2026.
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:03 pm -
2 stops27h 20m
Tue 12/19:45 pm -
2 stops17h 35m
Deal found 10/25![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 10/27. 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
Thu 12/37:55 am -
1 stop6h 50m
Deal found 10/27![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 10/25. 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 stop4h 15m
Tue 12/15:30 am -
1 stop4h 20m
Deal found 10/25![Southwest logo]()
$407
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:50 am -
2 stops20h 45m
Fri 12/48:05 pm -
2 stops17h 02m
Deal found 10/25![Delta logo]()
$415
This JetBlue deal was found by Cheapflights users on 10/27. 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 11/106:30 am -
1 stop4h 11m
Wed 11/116:39 pm -
1 stop5h 04m
Deal found 10/27![JetBlue logo]()
$431
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:27 am -
1 stop25h 55m
Fri 12/49:35 am -
2 stops13h 45m
Deal found 10/25![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:03 pm -
2 stops27h 20m
Mon 11/309:30 pm -
1 stop17h 50m
Deal found 10/25![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:03 pm -
2 stops27h 20m
Sun 11/299:00 pm -
1 stop13h 59m
Deal found 10/25![Delta logo]()
$470
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:50 am -
2 stops20h 45m
Wed 12/29:10 am -
1 stop15h 11m
Deal found 10/25![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:27 am -
1 stop6h 54m
Wed 12/212:49 pm -
2 stops10h 31m
Deal found 10/25![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:50 am -
2 stops20h 45m
Mon 11/309:30 pm -
1 stop17h 50m
Deal found 10/25![Delta logo]()
$486
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:50 am -
2 stops20h 45m
Sun 11/299:00 pm -
1 stop13h 59m
Deal found 10/25![Delta logo]()
$491
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 30, 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 30, 2026.
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:03 pm -
2 stops27h 20m
Thu 12/312:49 pm -
2 stops10h 31m
Deal found 10/25![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 10/27. 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
Thu 12/37:55 am -
1 stop6h 50m
Deal found 10/27![Southwest logo]()
$397
This JetBlue deal was found by Cheapflights users on 10/27. 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 11/106:30 am -
1 stop4h 11m
Wed 11/116:39 pm -
1 stop5h 04m
Deal found 10/27![JetBlue logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/263:10 pm -
2 stops19h 01m
Thu 12/311:08 am -
1 stop22h 00m
Deal found 10/27![Multiple Airlines logo]()
$529
This United Airlines deal was found by Cheapflights users on 10/25. 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 11/216:00 am -
2 stops17h 59m
Wed 12/25:45 am -
2 stops13h 40m
Deal found 10/25![United Airlines logo]()
$573
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:27 am -
1 stop25h 55m
Fri 12/49:35 am -
2 stops13h 45m
Deal found 10/25![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:39 am -
1 stop11h 38m
Wed 12/29:45 pm -
2 stops13h 15m
Deal found 10/25![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:50 am -
2 stops20h 45m
Mon 11/309:30 pm -
1 stop17h 50m
Deal found 10/25![Delta logo]()
$486
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:27 am -
1 stop7h 54m
Sun 11/299:00 pm -
1 stop13h 59m
Deal found 10/25![Delta logo]()
$534
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated October 30, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 10/27. 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 11/106:30 am -
1 stop4h 11m
Wed 11/116:39 pm -
1 stop5h 04m
Deal found 10/27![JetBlue logo]()
$431
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:27 am -
1 stop25h 55m
Fri 12/49:35 am -
2 stops13h 45m
Deal found 10/25![Delta logo]()
$457
This Southwest deal was found by Cheapflights users on 10/25. 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 stop4h 15m
Tue 12/15:30 am -
1 stop4h 20m
Deal found 10/25![Southwest logo]()
$407
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:27 am -
1 stop6h 54m
Wed 12/212:49 pm -
2 stops10h 31m
Deal found 10/25![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:03 pm -
2 stops27h 20m
Tue 12/19:45 pm -
2 stops17h 35m
Deal found 10/25![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:03 pm -
2 stops27h 20m
Mon 11/309:30 pm -
1 stop17h 50m
Deal found 10/25![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:03 pm -
2 stops27h 20m
Sun 11/299:00 pm -
1 stop13h 59m
Deal found 10/25![Delta logo]()
$470
This Southwest deal was found by Cheapflights users on 10/27. 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
Thu 12/37:55 am -
1 stop6h 50m
Deal found 10/27![Southwest logo]()
$397
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:50 am -
2 stops20h 45m
Fri 12/48:05 pm -
2 stops17h 02m
Deal found 10/25![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:50 am -
2 stops20h 45m
Wed 12/29:10 am -
1 stop15h 11m
Deal found 10/25![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:50 am -
2 stops20h 45m
Mon 11/309:30 pm -
1 stop17h 50m
Deal found 10/25![Delta logo]()
$486
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:50 am -
2 stops20h 45m
Sun 11/299:00 pm -
1 stop13h 59m
Deal found 10/25![Delta logo]()
$491
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 30, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/186:31 pm -
2 stops16h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:09 pm -
2 stops40h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 10/25. 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 12/13:25 pm -
1 stop6h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Southwest logo]()
$199
This Priceline deal was found by Cheapflights users on 10/28. 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 11/136:30 am -
1 stop3h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![JetBlue logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/133:53 pm -
3 stops17h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 10/26![Multiple Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/135:50 am -
2 stops13h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![United Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 10/28. 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 -
1 stop4h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$633
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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $393 (Delta) |
One-way from | $170 (Kiwi.com) |
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 30, 2026.
Use the filters below to find and compare flights from Portland to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Tue 12/1
5:09 pm-9:39 am
2 stops40h 30m
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 12/1
3:25 pm-9:55 pm
1 stop6h 30m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$199
Quickest round-trip
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Fri 11/13
6:30 am-10:16 am
1 stop3h 46m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$216
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Sat 11/14
6:30 am-10:46 am
1 stop4h 16m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$216
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Wed 11/18
6:30 am-10:41 am
1 stop4h 11m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$216
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Fri 11/13
3:53 pm-9:29 am
3 stops17h 36m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Wed 11/25
4:03 pm-7:23 pm
2 stops27h 20m
Boston Logan Intl
Thu 12/3
12:49 pm-11:20 pm
2 stops10h 31m
$393
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Thu 11/26
5:15 am-12:15 pm
1 stop7h 00m
Boston Logan Intl
Thu 12/3
7:55 am-2:45 pm
1 stop6h 50m
$397
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Fri 11/13
5:50 am-6:57 pm
2 stops13h 07m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$423
PortlandBoston
PWM Portland - BOS Boston Logan Intl
PWMBOS
Portland
Tue 11/10
6:30 am-10:41 am
1 stop4h 11m
Boston Logan Intl
Wed 11/11
6:39 pm-11:43 pm
1 stop5h 04m
$431
Showing 1-10 of 17 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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations