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Massachusetts

$155+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Apr 14 — Apr 211
Tue 4/14
Tue 4/21
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 March 15, 2026.

This JetBlue deal was found by Cheapflights users on 3/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
PWM
-
BOS
1 stop4h 38m
JetBlue
Mon 5/115:00 pm
BOS
-
PWM
1 stop6h 36m
JetBlue
Deal found 3/15$205
This Priceline deal was found by Cheapflights users on 3/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:00 am
PWM
-
BOS
1 stop4h 38m
JetBlue
Mon 5/115:00 pm
BOS
-
PWM
1 stop6h 36m
JetBlue
Deal found 3/10$207
This Expedia deal was found by Cheapflights users on 3/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:30 am
PWM
-
BOS
2 stops13h 55m
JetBlue
Tue 5/55:00 pm
BOS
-
PWM
1 stop6h 36m
JetBlue
Deal found 3/13$283
This Expedia deal was found by Cheapflights users on 3/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:00 am
PWM
-
BOS
1 stop8h 45m
JetBlue
Wed 4/86:02 pm
BOS
-
PWM
1 stop5h 56m
JetBlue
Deal found 3/14$303
This American Airlines deal was found by Cheapflights users on 3/13. 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 4/2810:24 am
PWM
-
BOS
1 stop9h 10m
American Airlines
Tue 5/512:52 pm
BOS
-
PWM
1 stop21h 02m
American Airlines
Deal found 3/13$311
This American Airlines deal was found by Cheapflights users on 3/13. 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 4/73:39 pm
PWM
-
BOS
1 stop17h 42m
American Airlines
Thu 4/92:48 pm
BOS
-
PWM
1 stop19h 06m
American Airlines
Deal found 3/13$323
This KAYAK deal was found by Cheapflights users on 3/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
PWM
-
BOS
1 stop4h 38m
JetBlue
Sat 5/95:25 pm
BOS
-
PWM
1 stop6h 11m
JetBlue
Deal found 3/14$339
This American Airlines deal was found by Cheapflights users on 3/12. 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.
Mon 5/43:39 pm
PWM
-
BOS
1 stop15h 41m
American Airlines
Sat 5/910:00 am
BOS
-
PWM
1 stop23h 54m
American Airlines
Deal found 3/12$341
This JetBlue deal was found by Cheapflights users on 3/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/44:25 pm
PWM
-
BOS
1 stop7h 54m
JetBlue
Wed 4/86:02 pm
BOS
-
PWM
1 stop5h 56m
JetBlue
Deal found 3/11$345
This Priceline deal was found by Cheapflights users on 3/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/92:25 pm
PWM
-
BOS
1 stop5h 39m
JetBlue
Thu 6/186:05 am
BOS
-
PWM
1 stop7h 24m
JetBlue
Deal found 3/12$364
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 5/411:29 am
PWM
-
BOS
2 stops14h 02m
Multiple Airlines
Sat 5/98:40 am
BOS
-
PWM
1 stop7h 36m
Multiple Airlines
Deal found 3/12$366
This Southwest deal was found by Cheapflights users on 3/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:30 am
PWM
-
BOS
1 stop5h 20m
Southwest
Sat 4/411:30 am
BOS
-
PWM
1 stop5h 15m
Southwest
Deal found 3/10$367

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 March 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$205
(JetBlue)

One-way from

$155
(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.
Search Deals
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 March 15, 2026.
Use the filters below to find and compare flights from Portland to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 5/4

6:00 am-10:38 am

1 stop4h 38m

Boston Logan Intl

Mon 5/11

5:00 pm-11:36 pm

1 stop6h 36m

$205

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 5/8

6:00 am-10:38 am

1 stop4h 38m

Boston Logan Intl

Mon 5/11

5:00 pm-11:36 pm

1 stop6h 36m

$207

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 4/28

10:24 am-7:34 pm

1 stop9h 10m

Boston Logan Intl

Tue 5/5

12:52 pm-9:54 am

1 stop21h 02m

$311

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 4/7

3:39 pm-9:21 am

1 stop17h 42m

Boston Logan Intl

Thu 4/9

2:48 pm-9:54 am

1 stop19h 06m

$323

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 5/4

6:00 am-10:38 am

1 stop4h 38m

Boston Logan Intl

Sat 5/9

5:25 pm-11:36 pm

1 stop6h 11m

$339

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 4/4

4:25 pm-12:19 am

1 stop7h 54m

Boston Logan Intl

Wed 4/8

6:02 pm-11:58 pm

1 stop5h 56m

$345

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 6/9

2:25 pm-8:04 pm

1 stop5h 39m

Boston Logan Intl

Thu 6/18

6:05 am-1:29 pm

1 stop7h 24m

$364

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 4/1

4:30 pm-11:25 pm

1 stop6h 55m

Boston Logan Intl

Thu 4/2

9:00 am-2:15 pm

1 stop5h 15m

$367
Quickest round-trip

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 3/31

5:30 am-10:50 am

1 stop5h 20m

Boston Logan Intl

Sat 4/4

11:30 am-4:45 pm

1 stop5h 15m

$367

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 8/17

7:40 am-2:55 pm

1 stop7h 15m

Boston Logan Intl

Sun 8/23

5:55 am-12:45 pm

1 stop6h 50m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/13

Showing 1-10 of 22 resultsSorted by cheapest first
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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 $117). Flying from Portland, Maine to Massachusetts in January is currently the most expensive (average of $480). 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?

    JetBlue and American Airlines can get you from Portland, Maine to Massachusetts in just under 4h 38m. Your travel time can differ by up to 4h 32m. 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, October is the cheapest month in which you can book a flight from Portland, Maine to Massachusetts (average of $117). Flying from Portland, Maine to Massachusetts in January is currently the most expensive (average of $480). 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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