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$199+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:16 amPWM - BOS
1 stop22h 36mMultiple Airlines
Wed 1/712:29 pmBOS - PWM
2 stops46h 20mMultiple Airlines
Deal found 12/10$434
This United Airlines deal was found by Cheapflights users on 12/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:01 pmPWM - BOS
2 stops15h 36mUnited Airlines
Wed 1/72:20 pmBOS - PWM
1 stop24h 11mUnited Airlines
Deal found 12/11$510
This American Airlines deal was found by Cheapflights users on 12/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:00 amPWM - BOS
1 stop8h 47mAmerican Airlines
Wed 1/79:30 amBOS - PWM
1 stop13h 24mAmerican Airlines
Deal found 12/11$622
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/229:46 amPWM - BOS
1 stop25h 48mMultiple Airlines
Fri 12/2610:57 amBOS - PWM
2 stops23h 39mMultiple Airlines
Deal found 12/10$628
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:30 amPWM - BOS
1 stop18h 24mUnited Airlines
Fri 12/265:20 amBOS - PWM
1 stop18h 39mUnited Airlines
Deal found 12/10$645
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2411:16 amPWM - BOS
1 stop22h 36mMultiple Airlines
Sun 12/286:00 amBOS - PWM
2 stops27h 06mMultiple Airlines
Deal found 12/9$665
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/163:00 pmPWM - BOS
1 stop6h 33mUnited Airlines
Wed 12/1712:02 pmBOS - PWM
1 stop6h 41mUnited Airlines
Deal found 12/10$1,028

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 December 12, 2025.

Round-trip from

$434
(Kiwi.com)

One-way from

$199
(Kiwi.com)
From Portland to Massachusetts
Search Deals
One-way flight from Portland to Massachusetts
Search Deals

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 December 12, 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

Wed 12/31

11:16 am-9:52 am

1 stop22h 36m

Boston Logan Intl

Wed 1/7

12:29 pm-10:49 am

2 stops46h 20m

$434

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 12/31

7:01 pm-10:37 am

2 stops15h 36m

Boston Logan Intl

Wed 1/7

2:20 pm-2:31 pm

1 stop24h 11m

$510

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 1/6

12:40 pm-11:21 am

1 stop22h 41m

Boston Logan Intl

Tue 1/13

6:05 am-10:54 pm

1 stop16h 49m

$515

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 1/7

2:31 pm-11:49 pm

1 stop9h 18m

Boston Logan Intl

Sat 1/10

9:30 am-6:54 pm

1 stop9h 24m

$555

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 2/3

11:12 am-11:49 pm

2 stops12h 37m

Boston Logan Intl

Wed 2/4

7:07 pm-2:31 pm

1 stop19h 24m

$571

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sun 1/25

11:01 am-8:59 am

2 stops45h 58m

Boston Logan Intl

Sun 2/1

7:00 am-9:07 am

1 stop26h 07m

$600

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 2/3

2:31 pm-11:49 pm

1 stop9h 18m

Boston Logan Intl

Thu 2/5

5:45 am-2:31 pm

1 stop8h 46m

$611

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 12/31

8:00 am-4:47 pm

1 stop8h 47m

Boston Logan Intl

Wed 1/7

6:05 am-3:31 pm

1 stop9h 26m

$622

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 12/22

9:46 am-11:34 am

1 stop25h 48m

Boston Logan Intl

Fri 12/26

10:57 am-10:36 am

2 stops23h 39m

$628

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 12/22

5:30 am-11:54 pm

1 stop18h 24m

Boston Logan Intl

Fri 12/26

5:20 am-11:59 pm

1 stop18h 39m

$645

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 18 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, September is the cheapest month in which you can book a flight from Portland, Maine to Massachusetts (average of $108). Flying from Portland, Maine to Massachusetts in December is currently the most expensive (average of $448). 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 December 12, 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.

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

    United Airlines and American Airlines can get you from Portland, Maine to Massachusetts in just under 15h 36m. Your travel time can differ by up to 7h 05m. The distance from Portland, Maine to Massachusetts is about 95 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, September is the cheapest month in which you can book a flight from Portland, Maine to Massachusetts (average of $108). Flying from Portland, Maine to Massachusetts in December is currently the most expensive (average of $448). 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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