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Portland

$102+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PWM
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$218
(Expedia)

One-way from

$102
(Priceline)
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 September 16, 2025.

This Expedia deal was found by Cheapflights users on 9/14. 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.
Mon 9/2912:20 pmBOS - PWM
1 stop9h 47mJetBlue
Fri 10/37:09 amPWM - BOS
1 stop4h 36mJetBlue
Deal found 9/14$218
This JetBlue deal was found by Cheapflights users on 9/14. 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.
Fri 10/245:15 pmBOS - PWM
1 stop5h 49mJetBlue
Sat 10/257:09 amPWM - BOS
1 stop4h 36mJetBlue
Deal found 9/14$232
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/77:00 amBOS - PWM
1 stop6h 22mJetBlue
Sun 10/127:09 amPWM - BOS
1 stop4h 36mJetBlue
Deal found 9/15$238
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/277:10 amBDL - PWM
1 stop6h 12mJetBlue
Sat 10/42:17 pmPWM - BDL
1 stop8h 10mJetBlue
Deal found 9/15$238
This Trip.com deal was found by Cheapflights users on 9/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:10 amBDL - PWM
1 stop15h 54mJetBlue
Tue 10/217:09 amPWM - BDL
1 stop15h 20mJetBlue
Deal found 9/14$244
This Expedia deal was found by Cheapflights users on 9/14. 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 10/145:15 pmBOS - PWM
1 stop5h 49mJetBlue
Wed 10/157:09 amPWM - BOS
1 stop6h 41mJetBlue
Deal found 9/14$267
This Expedia deal was found by Cheapflights users on 9/14. 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.
Fri 10/245:15 pmBOS - PWM
1 stop5h 49mJetBlue
Sun 10/267:01 amPWM - BOS
1 stop7h 59mJetBlue
Deal found 9/14$268
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/46:30 pmBDL - PWM
1 stop22h 55mBreeze Airways
Mon 12/811:21 amPWM - BDL
2 stops10h 04mBreeze Airways
Deal found 9/15$274
This JetBlue deal was found by Cheapflights users on 9/15. 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.
Sat 10/45:20 pmBOS - PWM
1 stop4h 42mJetBlue
Sat 10/117:09 amPWM - BOS
1 stop6h 40mJetBlue
Deal found 9/15$283
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:10 amBDL - PWM
1 stop15h 54mJetBlue
Sun 10/267:01 amPWM - BDL
1 stop15h 28mJetBlue
Deal found 9/15$291
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:10 amBDL - PWM
1 stop15h 54mJetBlue
Sun 10/267:01 amPWM - BDL
1 stop15h 28mJetBlue
Deal found 9/16$302
This Delta deal was found by Cheapflights users on 9/15. 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 11/255:45 amALB - PWM
1 stop5h 00mDelta
Wed 12/34:53 pmPWM - ALB
1 stop6h 42mDelta
Deal found 9/15$317

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 September 16, 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

Tue 9/30

7:08 am-1:22 pm

1 stop6h 14m

Portland

Sat 10/4

7:30 am-1:47 pm

1 stop6h 17m

$218

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Mon 9/29

12:20 pm-10:07 pm

1 stop9h 47m

Portland

Fri 10/3

7:09 am-11:45 am

1 stop4h 36m

$218

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Tue 10/14

5:15 pm-11:04 pm

1 stop5h 49m

Portland

Tue 10/21

7:09 am-11:45 am

1 stop4h 36m

$218

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Fri 10/24

5:15 pm-11:04 pm

1 stop5h 49m

Portland

Sat 10/25

7:09 am-11:45 am

1 stop4h 36m

$232

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Tue 10/7

7:00 am-1:22 pm

1 stop6h 22m

Portland

Sun 10/12

7:09 am-11:45 am

1 stop4h 36m

$238

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Sat 9/27

7:10 am-1:22 pm

1 stop6h 12m

Portland

Sat 10/4

2:17 pm-10:27 pm

1 stop8h 10m

$238

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Tue 10/14

7:10 am-11:04 pm

1 stop15h 54m

Portland

Tue 10/21

7:09 am-10:29 pm

1 stop15h 20m

$244

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Tue 10/14

5:15 pm-11:04 pm

1 stop5h 49m

Portland

Wed 10/15

7:09 am-1:50 pm

1 stop6h 41m

$267

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Fri 10/24

5:15 pm-11:04 pm

1 stop5h 49m

Portland

Sun 10/26

7:01 am-3:00 pm

1 stop7h 59m

$268

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Thu 12/4

6:30 pm-5:25 pm

1 stop22h 55m

Portland

Mon 12/8

11:21 am-9:25 pm

2 stops10h 04m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 54 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, January is the cheapest month in which you can book a flight from Massachusetts to Portland, Maine (average of $296). Flying from Massachusetts to Portland, Maine in July is currently the most expensive (average of $394). 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 04m. JetBlue 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 cheapest airlines to fly from Massachusetts to Portland, Maine one-way?

    The cheapest airlines for a one-way flight from Massachusetts to Portland, Maine are JetBlue ($102), American Airlines ($142), and Delta ($159).

  • 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.

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

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Portland, Maine (average of $296). Flying from Massachusetts to Portland, Maine in July is currently the most expensive (average of $394). 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
Brunswick
North Conway
Auburn
Conway
Lewiston

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Massachusetts to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Massachusetts to Portland

Discover the top airline that operate flights from Massachusetts to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$202Average$444FlexibilityNo cancel feeOn-time62%

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