Portland

$132+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PWM
Mar 7 — Mar 141
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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 February 5, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:00 am
BDL
-
PWM
1 stop11h 16m
Breeze Airways
Thu 8/277:56 pm
PWM
-
BDL
1 stop25h 39m
Breeze Airways
Deal found 2/4$281
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:00 am
BDL
-
PWM
1 stop11h 16m
Breeze Airways
Fri 8/286:13 pm
PWM
-
BDL
1 stop28h 59m
Breeze Airways
Deal found 2/4$297
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:30 am
ALB
-
PWM
1 stop5h 31m
Delta
Tue 9/155:59 pm
PWM
-
ALB
1 stop4h 53m
Delta
Deal found 2/4$315
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
BOS
-
PWM
1 stop9h 09m
American Airlines
Wed 4/223:39 pm
PWM
-
BOS
1 stop7h 15m
American Airlines
Deal found 2/3$323
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:05 am
BDL
-
PWM
1 stop6h 50m
Southwest
Wed 4/14:30 pm
PWM
-
BDL
1 stop6h 25m
Southwest
Deal found 2/4$327
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:35 pm
ALB
-
PWM
1 stop6h 30m
Southwest
Mon 3/165:30 pm
PWM
-
ALB
1 stop6h 45m
Southwest
Deal found 2/4$327
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
ALB
-
PWM
1 stop6h 25m
Southwest
Tue 9/1510:30 am
PWM
-
ALB
2 stops10h 50m
Southwest
Deal found 2/4$332
This Southwest deal was found by Cheapflights users on 2/3. 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.
Thu 8/1310:15 am
ALB
-
PWM
1 stop4h 45m
Southwest
Mon 8/175:55 am
PWM
-
ALB
1 stop3h 35m
Southwest
Deal found 2/3$337
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:35 am
ALB
-
PWM
1 stop5h 43m
Delta
Tue 3/105:48 pm
PWM
-
ALB
1 stop5h 12m
Delta
Deal found 2/2$341
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:00 am
BDL
-
PWM
1 stop11h 16m
Breeze Airways
Sat 8/295:01 pm
PWM
-
BDL
1 stop22h 19m
Breeze Airways
Deal found 2/4$342
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:31 pm
BOS
-
PWM
1 stop17h 10m
American Airlines
Sun 5/241:31 pm
PWM
-
BOS
1 stop8h 33m
American Airlines
Deal found 2/2$343
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 3/33:40 pm
ALB
-
PWM
1 stop6h 35m
Southwest
Tue 3/105:30 am
PWM
-
ALB
1 stop6h 15m
Southwest
Deal found 2/2$347

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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$323
(American Airlines)

One-way from

$132
(Kiwi.com)
Provider with most accurate pricing for Boston Logan Intl-Portland flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-Portland flights.
From Massachusetts to Portland
One-way flight from Massachusetts to Portland

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 February 5, 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

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Wed 4/15

6:00 am-3:09 pm

1 stop9h 09m

Portland

Wed 4/22

3:39 pm-10:54 pm

1 stop7h 15m

$323

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Wed 3/18

9:05 am-3:55 pm

1 stop6h 50m

Portland

Wed 4/1

4:30 pm-10:55 pm

1 stop6h 25m

$327

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Mon 3/9

5:35 pm-12:05 am

1 stop6h 30m

Portland

Mon 3/16

5:30 pm-12:15 am

1 stop6h 45m

$327

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Tue 3/3

5:35 am-11:18 am

1 stop5h 43m

Portland

Tue 3/10

5:48 pm-11:00 pm

1 stop5h 12m

$341

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Tue 3/3

3:40 pm-10:15 pm

1 stop6h 35m

Portland

Tue 3/10

5:30 am-11:45 am

1 stop6h 15m

$347

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Sun 3/1

7:30 am-11:20 pm

2 stops15h 50m

Portland

Sat 3/7

1:15 pm-7:38 am

2 stops18h 23m

$355

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Mon 3/2

6:00 am-1:43 pm

1 stop7h 43m

Portland

Sat 3/7

1:15 pm-7:38 am

2 stops18h 23m

$395

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Fri 2/27

6:00 am-12:18 am

1 stop18h 18m

Portland

Wed 3/4

6:30 am-6:21 pm

1 stop11h 51m

$395

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Fri 2/27

6:00 am-12:18 am

1 stop18h 18m

Portland

Thu 3/5

2:35 pm-7:30 am

1 stop16h 55m

$395

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Tue 3/3

6:00 am-12:18 am

1 stop18h 18m

Portland

Sat 3/7

1:15 pm-7:38 am

2 stops18h 23m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 36 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. American Airlines provides one of the quickest options available for as low as $341. 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?

  • 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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