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$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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PWM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 11, 2025.

Round-trip from

$202
(Southwest)

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 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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 11/123:40 pmBDL - PWM
1 stop6h 35mSouthwest
Sat 11/153:15 pmPWM - BDL
1 stop6h 45mSouthwest
Deal found 9/10$202
This JetBlue deal was found by Cheapflights users on 9/10. 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.
Wed 10/85:15 pmBOS - PWM
1 stop5h 49mJetBlue
Wed 10/157:09 amPWM - BOS
1 stop6h 41mJetBlue
Deal found 9/10$203
This JetBlue deal was found by Cheapflights users on 9/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:08 amBOS - PWM
1 stop6h 14mJetBlue
Tue 9/307:09 amPWM - BOS
1 stop4h 36mJetBlue
Deal found 9/11$223
This Priceline deal was found by Cheapflights users on 9/10. 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.
Wed 9/247:15 amBDL - PWM
1 stop6h 07mJetBlue
Sat 9/272:17 pmPWM - BDL
1 stop8h 12mJetBlue
Deal found 9/10$223
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline 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
Fri 10/177:09 amPWM - BOS
1 stop4h 36mJetBlue
Deal found 9/8$232
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/278:00 amBOS - PWM
1 stop8h 50mAmerican Airlines
Sat 10/48:40 amPWM - BOS
1 stop8h 52mAmerican Airlines
Deal found 9/9$253
This JetBlue deal was found by Cheapflights users on 9/9. 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 10/112:17 pmPWM - BOS
1 stop4h 06mJetBlue
Deal found 9/9$258
This Priceline deal was found by Cheapflights users on 9/9. 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 10/75:15 pmBOS - PWM
1 stop5h 49mJetBlue
Tue 10/147:09 amPWM - BOS
1 stop4h 36mJetBlue
Deal found 9/9$273
This Delta deal was found by Cheapflights users on 9/9. 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.
Fri 10/245:00 pmBOS - PWM
1 stop20h 58mDelta
Sun 10/266:50 amPWM - BOS
1 stop24h 30mDelta
Deal found 9/9$283
This Priceline deal was found by Cheapflights users on 9/9. 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.
Fri 9/265:19 pmBOS - PWM
1 stop4h 48mJetBlue
Mon 9/297:09 amPWM - BOS
1 stop4h 36mJetBlue
Deal found 9/9$308
This Southwest deal was found by Cheapflights users on 9/11. 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.
Thu 10/305:50 pmALB - PWM
1 stop6h 15mSouthwest
Mon 11/35:30 amPWM - ALB
1 stop10h 00mSouthwest
Deal found 9/11$311
This Southwest deal was found by Cheapflights users on 9/10. 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 10/205:35 amBDL - PWM
1 stop8h 30mSouthwest
Thu 10/2311:45 amPWM - BDL
1 stop6h 30mSouthwest
Deal found 9/10$327

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 11, 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

Wed 11/12

3:40 pm-10:15 pm

1 stop6h 35m

Portland

Sat 11/15

3:15 pm-10:00 pm

1 stop6h 45m

$202

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Sat 10/18

5:15 pm-11:04 pm

1 stop5h 49m

Portland

Fri 10/24

7:09 am-11:45 am

1 stop4h 36m

$203

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Mon 9/29

5:19 pm-10:07 pm

1 stop4h 48m

Portland

Wed 10/1

2:17 pm-9:29 pm

1 stop7h 12m

$223

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Tue 10/14

5:15 pm-11:04 pm

1 stop5h 49m

Portland

Fri 10/17

7:09 am-11:45 am

1 stop4h 36m

$232

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Wed 9/24

7:15 am-1:22 pm

1 stop6h 07m

Portland

Sat 9/27

7:09 am-10:29 pm

1 stop15h 20m

$244

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Tue 10/7

5:15 pm-11:04 pm

1 stop5h 49m

Portland

Tue 10/14

7:09 am-11:45 am

1 stop4h 36m

$273

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Fri 10/24

5:00 pm-1:58 pm

1 stop20h 58m

Portland

Sun 10/26

6:50 am-7:20 am

1 stop24h 30m

$283

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Thu 10/2

8:30 am-1:22 pm

1 stop4h 52m

Portland

Thu 10/16

7:09 am-11:45 am

1 stop4h 36m

$283

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Fri 9/26

5:19 pm-10:07 pm

1 stop4h 48m

Portland

Tue 9/30

7:09 am-11:45 am

1 stop4h 36m

$283

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-4:37 pm

1 stop9h 36m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 43 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 49m. Southwest provides one of the quickest options available for as low as $203. The distance between Massachusetts and Portland, Maine is about 95 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), Delta ($115), and American Airlines ($127).

  • 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.

  • 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$202Average$444FlexibilityNo cancel feeOn-time62%

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