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Massachusetts

$167+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/410:57 am
PWM
-
BOS
1 stop12h 22m
Multiple Airlines
Sun 2/83:43 pm
BOS
-
PWM
1 stop17h 24m
Multiple Airlines
Deal found 1/20$359
This American Airlines deal was found by Cheapflights users on 1/21. 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 3/1112:44 pm
PWM
-
BOS
1 stop10h 39m
American Airlines
Tue 3/178:00 am
BOS
-
PWM
1 stop10h 04m
American Airlines
Deal found 1/21$465
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/1110:57 am
PWM
-
BOS
1 stop22h 09m
Multiple Airlines
Tue 2/176:10 pm
BOS
-
PWM
2 stops16h 07m
Multiple Airlines
Deal found 1/19$550
This American Airlines deal was found by Cheapflights users on 1/21. 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 2/187:00 am
PWM
-
BOS
1 stop11h 09m
American Airlines
Wed 2/2510:00 am
BOS
-
PWM
1 stop12h 59m
American Airlines
Deal found 1/21$559
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Tue 2/176:14 pm
PWM
-
BOS
1 stop19h 41m
Multiple Airlines
Thu 2/1910:01 am
BOS
-
PWM
1 stop24h 48m
Multiple Airlines
Deal found 1/20$577
This American Airlines deal was found by Cheapflights users on 1/19. 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 2/1112:40 pm
PWM
-
BOS
1 stop7h 50m
American Airlines
Tue 2/172:31 pm
BOS
-
PWM
1 stop8h 28m
American Airlines
Deal found 1/19$588
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 3/116:18 pm
PWM
-
BOS
2 stops42h 35m
Multiple Airlines
Tue 3/174:23 pm
BOS
-
PWM
1 stop17h 54m
Multiple Airlines
Deal found 1/21$599
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/1810:57 am
PWM
-
BOS
1 stop11h 04m
Multiple Airlines
Wed 2/255:50 pm
BOS
-
PWM
2 stops40h 59m
Multiple Airlines
Deal found 1/21$600
This United Airlines deal was found by Cheapflights users on 1/19. 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 1/244:10 pm
PWM
-
BOS
1 stop20h 36m
United Airlines
Mon 1/2612:45 pm
BOS
-
PWM
1 stop25h 54m
United Airlines
Deal found 1/19$633

Find flight deals from Portland to Massachusetts

Keep the following information in mind while searching for Portland to Massachusetts flight deals. Data was last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$359
(Kiwi.com)

One-way from

$167
(American Airlines)
Provider with most accurate pricing for Portland-Boston Logan Intl flight deals.
Search Deals
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 January 21, 2026.
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

Wed 2/4

10:57 am-11:19 pm

1 stop12h 22m

Boston Logan Intl

Sun 2/8

3:43 pm-9:07 am

1 stop17h 24m

$359

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 3/11

12:44 pm-11:23 pm

1 stop10h 39m

Boston Logan Intl

Tue 3/17

8:00 am-6:04 pm

1 stop10h 04m

$465

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 2/11

10:57 am-9:06 am

1 stop22h 09m

Boston Logan Intl

Tue 2/17

6:10 pm-10:17 am

2 stops16h 07m

$550

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 2/18

7:00 am-6:09 pm

1 stop11h 09m

Boston Logan Intl

Wed 2/25

10:00 am-10:59 pm

1 stop12h 59m

$559

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 2/17

6:14 pm-1:55 pm

1 stop19h 41m

Boston Logan Intl

Thu 2/19

10:01 am-10:49 am

1 stop24h 48m

$577

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 2/11

12:40 pm-8:30 pm

1 stop7h 50m

Boston Logan Intl

Tue 2/17

2:31 pm-10:59 pm

1 stop8h 28m

$588

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 3/11

6:18 pm-12:53 pm

2 stops42h 35m

Boston Logan Intl

Tue 3/17

4:23 pm-10:17 am

1 stop17h 54m

$599

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 2/18

10:57 am-10:01 pm

1 stop11h 04m

Boston Logan Intl

Wed 2/25

5:50 pm-10:49 am

2 stops40h 59m

$600

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 2/5

3:58 pm-6:13 pm

1 stop26h 15m

Boston Logan Intl

Mon 2/9

6:00 am-10:54 pm

1 stop16h 54m

$686

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 5/1

5:10 pm-8:52 am

1 stop15h 42m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 19 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, October is the cheapest month in which you can book a flight from Portland, Maine to Massachusetts (average of $123). Flying from Portland, Maine to Massachusetts in December is currently the most expensive (average of $458). 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 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.

  • How long is the flight from Portland, Maine to Massachusetts?

    American Airlines can get you from Portland, Maine to Massachusetts in just under 10h 39m. Your travel time can differ by up to . The distance from Portland, Maine to Massachusetts is about 95 mi.

  • 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, October is the cheapest month in which you can book a flight from Portland, Maine to Massachusetts (average of $123). Flying from Portland, Maine to Massachusetts in December is currently the most expensive (average of $458). 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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