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$203+ Cheap flights from Portland, ME (PWM) to Massachusetts

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Fri 11/149:46 amPWM - BOS
1 stop22h 42mMultiple Airlines
Sun 11/168:40 amBOS - PWM
2 stops29h 11mMultiple Airlines
Deal found 10/27$293
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/126:18 pmPWM - BOS
2 stops29h 41mMultiple Airlines
Sun 11/1612:59 pmBOS - PWM
1 stop20h 07mMultiple Airlines
Deal found 10/28$309
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Tue 11/116:37 pmPWM - BOS
1 stop28h 17mAmerican Airlines
Sat 11/158:00 amBOS - PWM
1 stop10h 10mAmerican Airlines
Deal found 10/26$503
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/1212:38 pmPWM - BOS
1 stop10h 16mAmerican Airlines
Sat 11/158:00 amBOS - PWM
1 stop10h 10mAmerican Airlines
Deal found 10/29$543
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/136:37 pmPWM - BOS
1 stop14h 56mAmerican Airlines
Sun 11/166:00 amBOS - PWM
1 stop9h 19mAmerican Airlines
Deal found 10/26$557
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/610:49 amPWM - BOS
1 stop23h 44mMultiple Airlines
Fri 11/73:55 pmBOS - PWM
2 stops18h 46mMultiple Airlines
Deal found 10/28$661
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/2911:16 amPWM - BOS
1 stop22h 45mMultiple Airlines
Tue 12/25:45 pmBOS - PWM
1 stop16h 51mMultiple Airlines
Deal found 10/29$707
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/116:00 amPWM - BOS
1 stop6h 23mUnited Airlines
Thu 11/139:00 amBOS - PWM
1 stop4h 36mUnited Airlines
Deal found 10/29$755

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 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$232
(Priceline)

One-way from

$207
(Kiwi.com)
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 October 29, 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

Tue 3/31

2:20 pm-8:30 pm

1 stop6h 10m

Boston Logan Intl

Tue 4/7

8:30 am-1:23 pm

1 stop4h 53m

$203

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 4/6

2:20 pm-8:30 pm

1 stop6h 10m

Boston Logan Intl

Fri 4/10

8:30 am-1:23 pm

1 stop4h 53m

$232

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 11/14

9:46 am-8:28 am

1 stop22h 42m

Boston Logan Intl

Sun 11/16

8:40 am-1:51 pm

2 stops29h 11m

$293

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 11/12

6:18 pm-11:59 pm

2 stops29h 41m

Boston Logan Intl

Sun 11/16

12:59 pm-9:06 am

1 stop20h 07m

$309

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 3/31

6:00 am-5:28 pm

1 stop11h 28m

Boston Logan Intl

Tue 4/7

9:50 am-9:27 pm

2 stops11h 37m

$475

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 11/11

6:37 pm-10:54 pm

1 stop28h 17m

Boston Logan Intl

Sat 11/15

8:00 am-6:10 pm

1 stop10h 10m

$503

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 11/12

11:16 am-12:04 pm

1 stop24h 48m

Boston Logan Intl

Sat 11/15

1:36 pm-2:30 pm

2 stops24h 54m

$503

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 11/12

12:38 pm-10:54 pm

1 stop10h 16m

Boston Logan Intl

Sat 11/15

8:00 am-6:10 pm

1 stop10h 10m

$543

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 11/13

6:37 pm-9:33 am

1 stop14h 56m

Boston Logan Intl

Sun 11/16

6:00 am-3:19 pm

1 stop9h 19m

$557

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 11/29

11:16 am-10:01 am

1 stop22h 45m

Boston Logan Intl

Tue 12/2

5:45 pm-10:36 am

1 stop16h 51m

$707

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 16 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 29, 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 can get you from Portland, Maine to Massachusetts in just under 6h 10m. 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, 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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