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$160+ Cheap flights from Portland, ME (PWM) to Massachusetts

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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
1 adult, Economy
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Find flight deals from Portland to Massachusetts

Cheapest flights from Portland to Massachusetts
Explore the most affordable flight options available from Portland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1311:16 amPWM - BOS
2 stops12h 40mMultiple Airlines
Tue 1/133:43 pmBOS - PWM
1 stop18h 39mMultiple Airlines
Deal found 11/16$274
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
Mon 12/159:46 amPWM - BOS
1 stop24h 15mMultiple Airlines
Fri 12/1910:56 amBOS - PWM
1 stop23h 40mMultiple Airlines
Deal found 11/17$344
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/16:05 pmPWM - BOS
2 stops29h 48mMultiple Airlines
Fri 12/58:11 pmBOS - PWM
1 stop14h 25mMultiple Airlines
Deal found 11/16$386
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
Wed 12/1711:16 amPWM - BOS
1 stop22h 36mMultiple Airlines
Wed 12/2411:09 amBOS - PWM
2 stops24h 09mMultiple Airlines
Deal found 11/17$402
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1411:58 amPWM - BOS
2 stops19h 35mMultiple Airlines
Sun 12/2110:56 amBOS - PWM
1 stop22h 10mMultiple Airlines
Deal found 11/16$475
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/1810:49 amPWM - BOS
2 stops46h 21mMultiple Airlines
Thu 12/2510:47 amBOS - PWM
1 stop23h 54mMultiple Airlines
Deal found 11/18$486
This United Airlines deal was found by Cheapflights users on 11/18. 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.
Thu 12/185:30 amPWM - BOS
1 stop8h 50mUnited Airlines
Thu 12/257:32 pmBOS - PWM
1 stop3h 50mUnited Airlines
Deal found 11/18$500
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2211:21 amPWM - BOS
1 stop23h 03mMultiple Airlines
Mon 11/2411:04 pmBOS - PWM
2 stops19h 51mMultiple Airlines
Deal found 11/16$512
This American Airlines deal was found by Cheapflights users on 11/17. 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 12/173:55 pmPWM - BOS
1 stop20h 13mAmerican Airlines
Wed 12/247:56 amBOS - PWM
1 stop10h 15mAmerican Airlines
Deal found 11/17$522

Cheap flight deals from Portland to Massachusetts

Keep the following information in mind while searching for Portland to Massachusetts flight deals. Data was last updated November 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$274
(Kiwi.com)

One-way from

$160
(Kiwi.com)
Provider with most accurate pricing for Portland-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Portland-Boston Logan Intl flights.
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From Portland to Massachusetts
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One-way flight from Portland to Massachusetts
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Massachusetts 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 18, 2025.
Use the filters below to find and compare flights from Portland to Massachusetts that are best for you.

Fly from

Portland

Fly to

Massachusetts

Route

Depart

Return

Price

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 12/13

11:16 am-11:56 pm

2 stops12h 40m

Boston Logan Intl

Tue 1/13

3:43 pm-10:22 am

1 stop18h 39m

$274

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 12/15

9:46 am-10:01 am

1 stop24h 15m

Boston Logan Intl

Fri 12/19

10:56 am-10:36 am

1 stop23h 40m

$344

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 12/1

6:05 pm-11:53 pm

2 stops29h 48m

Boston Logan Intl

Fri 12/5

8:11 pm-10:36 am

1 stop14h 25m

$386

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 12/17

11:16 am-9:52 am

1 stop22h 36m

Boston Logan Intl

Wed 12/24

11:09 am-11:18 am

2 stops24h 09m

$402

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sun 12/14

11:58 am-7:33 am

2 stops19h 35m

Boston Logan Intl

Sun 12/21

10:56 am-9:06 am

1 stop22h 10m

$475

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 12/18

10:49 am-9:10 am

2 stops46h 21m

Boston Logan Intl

Thu 12/25

10:47 am-10:41 am

1 stop23h 54m

$486

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 12/18

5:30 am-2:20 pm

1 stop8h 50m

Boston Logan Intl

Thu 12/25

7:32 pm-11:22 pm

1 stop3h 50m

$500

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 11/22

11:21 am-10:24 am

1 stop23h 03m

Boston Logan Intl

Mon 11/24

11:04 pm-6:55 pm

2 stops19h 51m

$512

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 12/17

3:55 pm-12:08 pm

1 stop20h 13m

Boston Logan Intl

Wed 12/24

7:56 am-6:11 pm

1 stop10h 15m

$522

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 1/30

11:29 am-2:38 pm

3 stops27h 09m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/15

Showing 1-10 of 17 results
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Best time to book a flight from Portland to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Portland 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 Portland to Massachusetts

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

Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Massachusetts (average of $89). Flying from Portland, Maine to Massachusetts in December is currently the most expensive (average of $401). 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.

What is the cheapest time of day to fly from PWM to MA?

Find hourly flight availability from Portland to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 18, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 45% on flights from Portland, Maine to Massachusetts by exploring options for tickets in the evening.

Related info for your journey

Find useful and relevant information for your journey from Portland to Massachusetts. 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 from for flights from Portland to Massachusetts?

    If you book a flight to Massachusetts from Portland, you will be flying from Portland, which is the city’s only airport. Portland (PWM) is located 2.9 mi from the center of Portland.

  • Can I find deals for flights from Portland to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Portland to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Massachusetts.

  • Can I find deals for business class flights from Portland to Massachusetts?

    Yes. Cheapflights offers flight deals from Portland to Massachusetts 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 Portland, Maine to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Massachusetts (average of $89). Flying from Portland, Maine to Massachusetts in December is currently the most expensive (average of $401). 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

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