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$173+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PWM
Nov 12 — Nov 191
Wed 11/12
Wed 11/19
1 adult, Economy
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Find 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 October 13, 2025.

This American Airlines deal was found by Cheapflights users on 10/11. 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.
Mon 10/277:30 pmBOS - PWM
1 stop17h 05mAmerican Airlines
Fri 10/317:00 amPWM - BOS
1 stop8h 58mAmerican Airlines
Deal found 10/11$244
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 10/289:05 amBDL - PWM
1 stop25h 36mBreeze Airways
Sat 11/111:21 amPWM - BDL
1 stop11h 36mBreeze Airways
Deal found 10/13$309
This Southwest deal was found by Cheapflights users on 10/11. 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 11/1012:20 pmBDL - PWM
1 stop4h 30mSouthwest
Mon 11/173:30 pmPWM - BDL
1 stop4h 35mSouthwest
Deal found 10/11$327
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Sun 10/266:00 amBOS - PWM
1 stop17h 17mUnited Airlines
Tue 11/46:00 amPWM - BOS
1 stop9h 27mUnited Airlines
Deal found 10/11$328
This Southwest deal was found by Cheapflights users on 10/12. 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 11/215:40 amALB - PWM
1 stop5h 30mSouthwest
Sun 11/235:25 pmPWM - ALB
1 stop6h 20mSouthwest
Deal found 10/12$337
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/912:59 pmBOS - PWM
1 stop20h 07mMultiple Airlines
Sun 11/163:15 pmPWM - BOS
2 stops32h 44mMultiple Airlines
Deal found 10/12$344
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Tue 10/2810:20 amBOS - PWM
1 stop9h 54mAmerican Airlines
Sat 11/17:00 amPWM - BOS
1 stop13h 26mAmerican Airlines
Deal found 10/12$345
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 10/266:00 amBDL - PWM
2 stops27h 06mBreeze Airways
Wed 10/2911:21 amPWM - BDL
1 stop12h 36mBreeze Airways
Deal found 10/13$345
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/118:05 amBDL - PWM
2 stops26h 36mBreeze Airways
Tue 11/186:29 pmPWM - BDL
1 stop20h 47mBreeze Airways
Deal found 10/12$349
This American Airlines deal was found by Cheapflights users on 10/13. 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 10/3010:20 amBOS - PWM
1 stop9h 54mAmerican Airlines
Sat 11/18:19 amPWM - BOS
1 stop12h 07mAmerican Airlines
Deal found 10/13$350
This Southwest deal was found by Cheapflights users on 10/13. 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 11/65:40 pmBDL - PWM
1 stop6h 40mSouthwest
Sun 11/95:30 amPWM - BDL
1 stop6h 15mSouthwest
Deal found 10/13$367
This Delta deal was found by Cheapflights users on 10/11. 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 11/55:45 amALB - PWM
1 stop5h 04mDelta
Wed 11/55:00 pmPWM - ALB
1 stop6h 02mDelta
Deal found 10/11$367

Cheap flight deals from Massachusetts to Portland

Keep the following information in mind while searching for Massachusetts to Portland flight deals. Data was last updated October 13, 2025.

Round-trip from

$244
(American Airlines)

One-way from

$173
(Priceline)
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 October 13, 2025.
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

Mon 10/27

7:30 pm-12:35 pm

1 stop17h 05m

Portland

Fri 10/31

7:00 am-3:58 pm

1 stop8h 58m

$244

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Tue 10/28

9:05 am-10:41 am

1 stop25h 36m

Portland

Sat 11/1

11:21 am-10:57 pm

1 stop11h 36m

$309

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Tue 11/11

3:40 pm-10:15 pm

1 stop6h 35m

Portland

Tue 11/18

3:30 pm-10:05 pm

1 stop6h 35m

$327

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Mon 11/10

12:20 pm-4:50 pm

1 stop4h 30m

Portland

Mon 11/17

3:30 pm-8:05 pm

1 stop4h 35m

$327

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Sun 10/26

6:00 am-11:17 pm

1 stop17h 17m

Portland

Tue 11/4

6:00 am-3:27 pm

1 stop9h 27m

$328

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Fri 11/21

5:40 am-11:10 am

1 stop5h 30m

Portland

Sun 11/23

5:25 pm-11:45 pm

1 stop6h 20m

$337

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Tue 10/28

10:20 am-8:14 pm

1 stop9h 54m

Portland

Sat 11/1

7:00 am-8:26 pm

1 stop13h 26m

$345

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Sun 10/26

6:00 am-9:06 am

2 stops27h 06m

Portland

Wed 10/29

11:21 am-11:57 pm

1 stop12h 36m

$345

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Thu 10/30

10:20 am-8:14 pm

1 stop9h 54m

Portland

Sat 11/1

8:19 am-8:26 pm

1 stop12h 07m

$350

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Wed 11/5

5:45 am-10:49 am

1 stop5h 04m

Portland

Wed 11/5

5:00 pm-11:02 pm

1 stop6h 02m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 38 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 6h 35m. American Airlines provides one of the quickest options available for as low as $327. The distance between Massachusetts and Portland, Maine is about 169 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 Hartford Bradley Intl - Portland. You may also consider Boston Logan Intl - Portland or Albany 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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