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$141+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PWM
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$252
(Kiwi.com)

One-way from

$141
(Kiwi.com)
Provider with most accurate pricing for Boston Logan Intl-Portland flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Portland flights.
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From Massachusetts to Portland
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One-way flight from Massachusetts to Portland
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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 January 8, 2026.

This Delta deal was found by Cheapflights users on 1/7. 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 2/35:40 amALB - PWM
1 stop5h 40mDelta
Wed 2/45:59 pmPWM - ALB
1 stop4h 56mDelta
Deal found 1/7$271
This Southwest deal was found by Cheapflights users on 1/6. 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 2/39:25 amBDL - PWM
1 stop5h 30mSouthwest
Wed 2/45:45 amPWM - BDL
1 stop5h 50mSouthwest
Deal found 1/6$272
This Southwest deal was found by Cheapflights users on 1/7. 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 2/35:30 amALB - PWM
2 stops9h 25mSouthwest
Wed 2/412:45 pmPWM - ALB
1 stop5h 40mSouthwest
Deal found 1/7$277
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 1/224:48 pmBDL - PWM
1 stop23h 38mBreeze Airways
Mon 1/269:47 amPWM - BDL
2 stops13h 29mBreeze Airways
Deal found 1/7$281
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/2212:01 pmALB - PWM
1 stop22h 48mBreeze Airways
Mon 1/2611:29 amPWM - ALB
1 stop24h 56mBreeze Airways
Deal found 1/6$281
This Expedia deal was found by Cheapflights users on 1/8. 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.
Tue 5/126:45 amBDL - PWM
1 stop6h 38mJetBlue
Wed 5/132:18 pmPWM - BDL
1 stop9h 26mJetBlue
Deal found 1/8$284
This Southwest deal was found by Cheapflights users on 1/6. 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 2/56:00 amBDL - PWM
1 stop6h 25mSouthwest
Thu 2/125:30 amPWM - BDL
1 stop6h 35mSouthwest
Deal found 1/6$313
This Delta deal was found by Cheapflights users on 1/8. 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 2/125:35 amALB - PWM
1 stop5h 43mDelta
Sun 2/155:59 pmPWM - ALB
1 stop5h 03mDelta
Deal found 1/8$313
This Southwest deal was found by Cheapflights users on 1/6. 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 2/68:35 amBDL - PWM
1 stop3h 50mSouthwest
Sun 2/85:45 amPWM - BDL
1 stop5h 50mSouthwest
Deal found 1/6$337
This Southwest deal was found by Cheapflights users on 1/8. 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 3/138:55 amALB - PWM
1 stop7h 50mSouthwest
Mon 3/165:30 pmPWM - ALB
1 stop6h 45mSouthwest
Deal found 1/8$339
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/237:13 pmBDL - PWM
2 stops15h 09mBreeze Airways
Sun 1/256:19 pmPWM - BDL
1 stop18h 52mBreeze Airways
Deal found 1/6$340
This American Airlines deal was found by Cheapflights users on 1/7. 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 7/236:00 amBOS - PWM
1 stop8h 03mAmerican Airlines
Mon 7/271:31 pmPWM - BOS
1 stop18h 02mAmerican Airlines
Deal found 1/7$351

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 8, 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

Tue 2/3

5:40 am-11:20 am

1 stop5h 40m

Portland

Wed 2/4

5:59 pm-10:55 pm

1 stop4h 56m

$271

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Tue 2/3

9:25 am-2:55 pm

1 stop5h 30m

Portland

Wed 2/4

5:45 am-11:35 am

1 stop5h 50m

$272

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Tue 2/3

5:30 am-2:55 pm

2 stops9h 25m

Portland

Wed 2/4

12:45 pm-6:25 pm

1 stop5h 40m

$277

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Thu 1/22

12:01 pm-10:49 am

1 stop22h 48m

Portland

Mon 1/26

11:29 am-12:25 pm

1 stop24h 56m

$281

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Tue 5/12

6:45 am-1:23 pm

1 stop6h 38m

Portland

Wed 5/13

2:18 pm-11:44 pm

1 stop9h 26m

$284

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Thu 1/22

4:48 pm-4:26 pm

1 stop23h 38m

Portland

Mon 1/26

11:29 am-5:48 pm

1 stop6h 19m

$303

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Thu 2/12

5:35 am-11:18 am

1 stop5h 43m

Portland

Sun 2/15

5:59 pm-11:02 pm

1 stop5h 03m

$313

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Fri 2/6

6:00 am-12:25 pm

1 stop6h 25m

Portland

Sun 2/8

12:45 pm-5:15 pm

1 stop4h 30m

$337

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Fri 1/23

7:13 pm-10:22 am

2 stops15h 09m

Portland

Sun 1/25

6:19 pm-1:11 pm

1 stop18h 52m

$340

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Fri 3/13

7:55 am-4:45 pm

2 stops8h 50m

Portland

Mon 3/16

5:30 pm-12:15 am

1 stop6h 45m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 45 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 30m. Delta provides one of the quickest options available for as low as $272. 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 Boston Logan Intl - Portland. You may also consider Hartford Bradley 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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