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$113+ Cheap flights from Massachusetts to Portland, ME (PWM)

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 3/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PWM
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Massachusetts to Portland

Cheapest flights from Massachusetts to Portland
Explore the most affordable flight options available from Massachusetts to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Delta deal was found by Cheapflights users on 1/19. 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 3/25:35 am
ALB
-
PWM
1 stop5h 43m
Delta
Wed 3/45:59 pm
PWM
-
ALB
1 stop5h 03m
Delta
Deal found 1/19$321
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/2610:01 am
BOS
-
PWM
1 stop24h 48m
Multiple Airlines
Wed 3/410:57 am
PWM
-
BOS
1 stop11h 04m
Multiple Airlines
Deal found 1/21$341
This Southwest deal was found by Cheapflights users on 1/20. 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 5/209:10 am
ALB
-
PWM
1 stop6h 10m
Southwest
Wed 5/271:00 pm
PWM
-
ALB
1 stop5h 45m
Southwest
Deal found 1/20$347
This American Airlines deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1512:27 pm
BOS
-
PWM
1 stop8h 52m
American Airlines
Thu 8/201:14 pm
PWM
-
BOS
1 stop8h 36m
American Airlines
Deal found 1/21$358
This Delta deal was found by Cheapflights users on 1/21. 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 3/287:00 am
ALB
-
PWM
1 stop5h 31m
Delta
Sun 3/295:48 pm
PWM
-
ALB
1 stop5h 12m
Delta
Deal found 1/21$367
This Southwest deal was found by Cheapflights users on 1/21. 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 3/285:40 pm
ALB
-
PWM
1 stop6h 30m
Southwest
Sun 3/295:30 am
PWM
-
ALB
1 stop6h 45m
Southwest
Deal found 1/21$396
This JetBlue deal was found by Cheapflights users on 1/21. 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 9/177:08 am
BOS
-
PWM
1 stop6h 14m
JetBlue
Sun 9/207:09 am
PWM
-
BOS
1 stop4h 36m
JetBlue
Deal found 1/21$403
This American Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 am
ALB
-
PWM
2 stops10h 40m
American Airlines
Wed 5/276:00 am
PWM
-
ALB
1 stop8h 30m
American Airlines
Deal found 1/20$409
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/58:31 pm
BDL
-
PWM
1 stop12h 36m
Multiple Airlines
Mon 2/95:06 pm
PWM
-
BDL
2 stops40h 17m
Multiple Airlines
Deal found 1/21$414
This American Airlines deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:00 am
BDL
-
PWM
1 stop18h 43m
American Airlines
Mon 2/912:46 pm
PWM
-
BDL
1 stop10h 58m
American Airlines
Deal found 1/21$427
This American Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/67:40 pm
BDL
-
PWM
1 stop16h 26m
American Airlines
Sun 2/85:20 am
PWM
-
BDL
2 stops17h 23m
American Airlines
Deal found 1/20$463
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/176:10 pm
BOS
-
PWM
2 stops16h 07m
Multiple Airlines
Tue 2/246:14 pm
PWM
-
BOS
1 stop19h 41m
Multiple Airlines
Deal found 1/20$466

Find flight deals from Massachusetts to Portland

Keep the following information in mind while searching for Massachusetts to Portland flight deals. Data was last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$321
(Delta)

One-way from

$113
(Expedia)
Provider with most accurate pricing for Boston Logan Intl-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Portland flights.
Search Deals
From Massachusetts to Portland
Search Deals
One-way flight from Massachusetts to Portland
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Portland 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 January 21, 2026.
Use the filters below to find and compare flights from Massachusetts to Portland that are best for you.

Fly from

Massachusetts

Fly to

Portland

Route

Depart

Return

Price

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Mon 3/2

5:35 am-11:18 am

1 stop5h 43m

Portland

Wed 3/4

5:59 pm-11:02 pm

1 stop5h 03m

$321

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Thu 2/26

10:01 am-10:49 am

1 stop24h 48m

Portland

Wed 3/4

10:57 am-10:01 pm

1 stop11h 04m

$341

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Wed 5/20

9:10 am-3:20 pm

1 stop6h 10m

Portland

Wed 5/27

1:00 pm-6:45 pm

1 stop5h 45m

$347

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Sat 3/28

7:00 am-12:31 pm

1 stop5h 31m

Portland

Sun 3/29

5:48 pm-11:00 pm

1 stop5h 12m

$367

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Sat 3/28

5:40 pm-12:10 am

1 stop6h 30m

Portland

Sun 3/29

5:30 am-12:15 pm

1 stop6h 45m

$396

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Wed 5/20

6:00 am-4:40 pm

2 stops10h 40m

Portland

Wed 5/27

6:00 am-2:30 pm

1 stop8h 30m

$409

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Thu 2/5

8:31 pm-9:07 am

1 stop12h 36m

Portland

Mon 2/9

5:06 pm-9:23 am

2 stops40h 17m

$414

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Thu 2/5

5:00 am-11:43 pm

1 stop18h 43m

Portland

Mon 2/9

12:46 pm-11:44 pm

1 stop10h 58m

$427

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Fri 2/6

12:10 pm-12:06 pm

1 stop23h 56m

Portland

Sun 2/8

12:46 pm-11:44 pm

1 stop10h 58m

$427

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Thu 2/19

11:33 am-11:50 pm

2 stops12h 17m

Portland

Thu 2/26

6:00 am-8:12 am

1 stop26h 12m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 43 results
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Best time to book a flight from Massachusetts to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Massachusetts with our price prediction graph.
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 Massachusetts to Portland
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 Massachusetts to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Massachusetts?

    Portland (PWM), located 2.9 mi from the city center, is the airport you fly into when you book flights from Massachusetts to Portland.

  • How long is the flight from Massachusetts to Portland, Maine?

    A quick flight from Massachusetts to Portland, Maine can take about 5h 43m. Delta provides one of the quickest options available for as low as $321. The distance between Massachusetts and Portland, Maine is about 187 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Massachusetts to Portland, Maine?

    The most popular route from Massachusetts to Portland, Maine is Boston Logan Intl - Portland. You may also consider Albany Intl - Portland or Hartford Bradley Intl - Portland.

  • Can I find deals for flights from Massachusetts to Portland that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Portland.

  • Can I find deals for business class flights from Massachusetts to Portland?

    Yes. Cheapflights offers flight deals from Massachusetts to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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