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$184+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
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 October 22, 2025.

This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/264:40 pmPWM - BOS
1 stop16h 38mDelta
Fri 11/286:05 amBOS - PWM
1 stop17h 54mDelta
Deal found 10/20$358
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Sat 11/811:21 amPWM - BOS
1 stop22h 37mMultiple Airlines
Tue 11/1112:00 pmBOS - PWM
2 stops22h 36mMultiple Airlines
Deal found 10/21$382
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/1911:21 amPWM - BOS
1 stop23h 03mMultiple Airlines
Wed 11/269:54 pmBOS - PWM
2 stops19h 06mMultiple Airlines
Deal found 10/20$386
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Thu 10/303:15 pmPWM - BOS
2 stops17h 13mMultiple Airlines
Fri 10/312:15 pmBOS - PWM
1 stop20h 21mMultiple Airlines
Deal found 10/20$398
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:22 pmPWM - BOS
1 stop23h 26mUnited Airlines
Tue 11/119:30 amBOS - PWM
1 stop24h 34mUnited Airlines
Deal found 10/21$400
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/1011:16 amPWM - BOS
1 stop9h 21mMultiple Airlines
Wed 12/2411:09 amBOS - PWM
2 stops45h 57mMultiple Airlines
Deal found 10/21$422
This American Airlines deal was found by Cheapflights users on 10/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:00 amPWM - BOS
1 stop8h 58mAmerican Airlines
Fri 10/317:30 pmBOS - PWM
1 stop16h 38mAmerican Airlines
Deal found 10/20$423
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sat 11/1511:16 amPWM - BOS
2 stops11h 06mMultiple Airlines
Sun 11/1612:59 pmBOS - PWM
1 stop20h 07mMultiple Airlines
Deal found 10/20$426
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/122:20 pmPWM - BOS
1 stop9h 22mUnited Airlines
Sat 11/155:30 amBOS - PWM
1 stop8h 49mUnited Airlines
Deal found 10/22$430
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/59:45 amPWM - BOS
1 stop9h 40mUnited Airlines
Mon 12/85:30 amBOS - PWM
1 stop8h 49mUnited Airlines
Deal found 10/20$481

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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$348
(Priceline)

One-way from

$184
(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 October 22, 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

Thu 4/16

2:20 pm-8:30 pm

1 stop6h 10m

Boston Logan Intl

Thu 4/23

8:30 am-1:23 pm

1 stop4h 53m

$348

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 11/26

4:40 pm-9:18 am

1 stop16h 38m

Boston Logan Intl

Fri 11/28

6:05 am-11:59 pm

1 stop17h 54m

$358

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 11/8

11:21 am-9:58 am

1 stop22h 37m

Boston Logan Intl

Tue 11/11

12:00 pm-10:36 am

2 stops22h 36m

$382

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 11/19

11:21 am-10:24 am

1 stop23h 03m

Boston Logan Intl

Wed 11/26

9:54 pm-5:00 pm

2 stops19h 06m

$386

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 11/8

5:30 am-11:42 pm

1 stop18h 12m

Boston Logan Intl

Tue 11/11

9:30 am-10:04 am

1 stop24h 34m

$400

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 11/7

7:22 pm-6:48 pm

1 stop23h 26m

Boston Logan Intl

Tue 11/11

9:30 am-11:01 pm

2 stops13h 31m

$405

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 12/10

11:16 am-8:37 pm

1 stop9h 21m

Boston Logan Intl

Wed 12/24

11:09 am-9:06 am

2 stops45h 57m

$422

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 11/15

11:16 am-10:22 pm

2 stops11h 06m

Boston Logan Intl

Sun 11/16

12:59 pm-9:06 am

1 stop20h 07m

$426

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 11/12

2:20 pm-11:42 pm

1 stop9h 22m

Boston Logan Intl

Sat 11/15

5:30 am-2:19 pm

1 stop8h 49m

$430

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 12/5

9:45 am-7:25 pm

1 stop9h 40m

Boston Logan Intl

Mon 12/8

5:30 am-2:19 pm

1 stop8h 49m

$481

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

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, 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 October 22, 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?

    JetBlue, Delta, and United Airlines can get you from Portland, Maine to Massachusetts in just under 6h 10m. Your travel time can differ by up to 12h 02m. 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, 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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