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$116+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PWM
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
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 November 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/147:10 amBDL - PWM
2 stops34h 28mBreeze Airways
Mon 11/172:36 pmPWM - BDL
1 stop8h 02mBreeze Airways
Deal found 11/1$314
This Southwest deal was found by Cheapflights users on 11/2. 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.
Sat 11/226:00 pmBDL - PWM
1 stop6h 20mSouthwest
Sun 11/235:25 pmPWM - BDL
1 stop6h 15mSouthwest
Deal found 11/2$409
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/1612:59 pmBOS - PWM
1 stop20h 07mMultiple Airlines
Thu 11/203:15 pmPWM - BOS
2 stops25h 35mMultiple Airlines
Deal found 11/1$456
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/147:46 pmBDL - PWM
1 stop16h 00mAmerican Airlines
Mon 11/175:43 amPWM - BDL
1 stop18h 01mAmerican Airlines
Deal found 11/1$457
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/298:24 amBOS - PWM
2 stops30h 06mMultiple Airlines
Sat 12/611:16 amPWM - BOS
1 stop22h 11mMultiple Airlines
Deal found 11/1$472
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 11/225:06 amBDL - PWM
2 stops13h 04mAmerican Airlines
Sun 11/2312:47 pmPWM - BDL
2 stops10h 56mAmerican Airlines
Deal found 11/2$483
This United Airlines deal was found by Cheapflights users on 11/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:00 amBDL - PWM
2 stops17h 17mUnited Airlines
Sun 11/237:22 pmPWM - BDL
1 stop18h 44mUnited Airlines
Deal found 11/2$522
This Southwest deal was found by Cheapflights users on 11/2. 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.
Sun 11/303:50 pmALB - PWM
1 stop8h 20mSouthwest
Sun 12/75:25 pmPWM - ALB
1 stop6h 20mSouthwest
Deal found 11/2$525
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/85:30 amBDL - PWM
1 stop11h 08mAmerican Airlines
Wed 11/1212:26 pmPWM - BDL
1 stop11h 18mAmerican Airlines
Deal found 11/1$547
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/269:00 amBDL - PWM
2 stops13h 46mAmerican Airlines
Sat 11/295:43 amPWM - BDL
2 stops12h 47mAmerican Airlines
Deal found 11/1$563
This United Airlines deal was found by Cheapflights users on 11/1. 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 11/147:55 pmBDL - PWM
2 stops27h 22mUnited Airlines
Mon 11/173:20 pmPWM - BDL
2 stops18h 18mUnited Airlines
Deal found 11/1$588
This United Airlines deal was found by Cheapflights users on 11/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:00 amALB - PWM
1 stop8h 12mUnited Airlines
Mon 11/107:22 pmPWM - ALB
1 stop4h 21mUnited Airlines
Deal found 11/2$637

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 November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$314
(Kiwi.com)

One-way from

$116
(Kiwi.com)
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
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One-way flight from Massachusetts to Portland
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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 November 2, 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

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Fri 11/14

1:36 pm-10:36 am

1 stop21h 00m

Portland

Mon 11/17

2:36 pm-10:38 pm

1 stop8h 02m

$314

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Tue 3/31

6:00 am-11:57 am

1 stop5h 57m

Portland

Wed 4/1

4:50 pm-11:14 pm

1 stop6h 24m

$317

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Fri 1/23

5:35 am-11:20 am

1 stop5h 45m

Portland

Sun 1/25

5:56 pm-10:55 pm

1 stop4h 59m

$327

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Sat 11/22

6:00 pm-12:20 am

1 stop6h 20m

Portland

Sun 11/23

5:25 pm-11:40 pm

1 stop6h 15m

$409

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Sun 11/16

12:59 pm-9:06 am

1 stop20h 07m

Portland

Thu 11/20

3:15 pm-4:50 pm

2 stops25h 35m

$456

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Sat 11/29

8:24 am-2:30 pm

2 stops30h 06m

Portland

Sat 12/6

11:16 am-9:27 am

1 stop22h 11m

$472

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Sat 11/22

6:00 am-11:17 pm

2 stops17h 17m

Portland

Sun 11/23

7:22 pm-2:06 pm

1 stop18h 44m

$522

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Sun 11/30

3:50 pm-12:10 am

1 stop8h 20m

Portland

Sun 12/7

5:25 pm-11:45 pm

1 stop6h 20m

$525

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Fri 11/14

7:46 pm-11:46 am

1 stop16h 00m

Portland

Mon 11/17

5:43 am-6:29 pm

2 stops12h 46m

$545

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Wed 11/26

9:00 am-10:46 pm

2 stops13h 46m

Portland

Sat 11/29

5:43 am-6:30 pm

2 stops12h 47m

$563

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 29 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

What is the cheapest month to book a flight from Massachusetts to Portland, Maine?

Currently, July is the cheapest month in which you can book a flight from Massachusetts to Portland, Maine (average of $94). Flying from Massachusetts to Portland, Maine in February is currently the most expensive (average of $436). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 57m. Delta provides one of the quickest options available for as low as $317. 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 Hartford Bradley Intl - Portland. You may also consider Albany Intl - Portland or Boston Logan 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.

  • What is the cheapest month to book a flight from Massachusetts to Portland, Maine?

    Currently, July is the cheapest month in which you can book a flight from Massachusetts to Portland, Maine (average of $94). Flying from Massachusetts to Portland, Maine in February is currently the most expensive (average of $436). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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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