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$114+ 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 6/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
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 May 10, 2026.

This JetBlue deal was found by Cheapflights users on 5/7. 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.
Tue 9/11:17 pm
PWM
-
BOS
1 stop5h 28m
JetBlue
Wed 9/28:30 pm
BOS
-
PWM
1 stop3h 44m
JetBlue
Deal found 5/7$227
This JetBlue deal was found by Cheapflights users on 5/8. 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 6/226:00 am
PWM
-
BOS
1 stop5h 35m
JetBlue
Mon 6/298:43 am
BOS
-
PWM
1 stop4h 52m
JetBlue
Deal found 5/8$261
This JetBlue deal was found by Cheapflights users on 5/5. 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 5/236:00 am
PWM
-
BOS
1 stop5h 36m
JetBlue
Wed 5/276:40 pm
BOS
-
PWM
1 stop5h 18m
JetBlue
Deal found 5/5$270
This JetBlue deal was found by Cheapflights users on 5/7. 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.
Thu 5/286:00 am
PWM
-
BOS
1 stop5h 02m
JetBlue
Wed 6/37:03 am
BOS
-
PWM
1 stop6h 32m
JetBlue
Deal found 5/7$295
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Fri 5/221:35 pm
PWM
-
BOS
1 stop8h 53m
American Airlines
Mon 5/256:00 am
BOS
-
PWM
1 stop6h 40m
American Airlines
Deal found 5/5$313
This Priceline deal was found by Cheapflights users on 5/7. 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.
Thu 6/256:00 am
PWM
-
BOS
1 stop5h 26m
JetBlue
Tue 6/308:43 am
BOS
-
PWM
1 stop3h 47m
JetBlue
Deal found 5/7$328
This JetBlue deal was found by Cheapflights users on 5/6. 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.
Tue 5/266:00 am
PWM
-
BOS
1 stop5h 01m
JetBlue
Wed 5/277:03 am
BOS
-
PWM
1 stop6h 32m
JetBlue
Deal found 5/6$330
This Southwest deal was found by Cheapflights users on 5/6. 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.
Mon 11/95:20 am
PWM
-
BOS
1 stop6h 55m
Southwest
Wed 11/118:00 am
BOS
-
PWM
1 stop6h 50m
Southwest
Deal found 5/6$347
This Priceline deal was found by Cheapflights users on 5/6. 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.
Sun 6/216:00 am
PWM
-
BOS
1 stop5h 35m
JetBlue
Sun 6/217:15 pm
BOS
-
PWM
1 stop5h 10m
JetBlue
Deal found 5/6$359
This Expedia deal was found by Cheapflights users on 5/7. 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.
Fri 5/222:36 pm
PWM
-
BOS
1 stop9h 25m
JetBlue
Tue 5/266:40 pm
BOS
-
PWM
1 stop5h 18m
JetBlue
Deal found 5/7$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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$227
(JetBlue)

One-way from

$114
(Priceline)
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 May 10, 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 6/1

6:00 am-11:02 am

1 stop5h 02m

Boston Logan Intl

Wed 6/3

6:40 pm-11:58 pm

1 stop5h 18m

$227

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 6/10

6:00 am-11:02 am

1 stop5h 02m

Boston Logan Intl

Wed 6/17

7:03 pm-12:25 am

1 stop5h 22m

$227

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 9/1

1:17 pm-6:45 pm

1 stop5h 28m

Boston Logan Intl

Wed 9/2

7:05 pm-12:14 am

1 stop5h 09m

$227

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 6/27

6:45 am-11:35 am

1 stop4h 50m

Boston Logan Intl

Fri 7/3

7:05 pm-12:25 am

1 stop5h 20m

$261

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 6/22

6:00 am-11:35 am

1 stop5h 35m

Boston Logan Intl

Mon 6/29

8:43 am-1:35 pm

1 stop4h 52m

$261

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 5/23

6:00 am-11:36 am

1 stop5h 36m

Boston Logan Intl

Wed 5/27

6:40 pm-11:58 pm

1 stop5h 18m

$270
Quickest round-trip

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 6/18

2:30 pm-6:32 pm

1 stop4h 02m

Boston Logan Intl

Sat 6/20

8:30 pm-12:25 am

1 stop3h 55m

$294

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 5/28

6:00 am-11:02 am

1 stop5h 02m

Boston Logan Intl

Wed 6/3

7:03 am-1:35 pm

1 stop6h 32m

$295

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 5/22

1:35 pm-10:28 pm

1 stop8h 53m

Boston Logan Intl

Mon 5/25

6:00 am-12:40 pm

1 stop6h 40m

$313

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 6/25

6:00 am-11:26 am

1 stop5h 26m

Boston Logan Intl

Tue 6/30

8:43 am-12:30 pm

1 stop3h 47m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

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
No data available for this route at this time. Please check back soon.

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 5h 02m. 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.

See more FAQs

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