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Massachusetts

$118+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Jul 9 — Jul 161
Thu 7/9
Thu 7/16
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 June 9, 2026.

This JetBlue deal was found by Cheapflights users on 6/5. 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.
Fri 7/32:30 pm
PWM
-
BOS
1 stop4h 19m
JetBlue
Fri 7/107:39 pm
BOS
-
PWM
1 stop4h 37m
JetBlue
Deal found 6/5$237
This JetBlue deal was found by Cheapflights users on 6/7. 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.
Sat 7/42:30 pm
PWM
-
BOS
1 stop4h 19m
JetBlue
Sun 7/58:43 am
BOS
-
PWM
1 stop3h 47m
JetBlue
Deal found 6/7$271
This JetBlue deal was found by Cheapflights users on 6/4. 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.
Fri 6/266:00 am
PWM
-
BOS
1 stop5h 35m
JetBlue
Fri 7/34:40 pm
BOS
-
PWM
1 stop7h 45m
JetBlue
Deal found 6/4$294
This Expedia deal was found by Cheapflights users on 6/4. 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.
Thu 7/22:30 pm
PWM
-
BOS
1 stop9h 40m
JetBlue
Thu 7/96:05 pm
BOS
-
PWM
1 stop6h 11m
JetBlue
Deal found 6/4$376
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:01 pm
PWM
-
BOS
2 stops16h 08m
Multiple Airlines
Wed 7/88:41 am
BOS
-
PWM
1 stop7h 35m
Multiple Airlines
Deal found 6/8$384
This Southwest deal was found by Cheapflights users on 6/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:40 am
PWM
-
BOS
1 stop7h 15m
Southwest
Mon 8/173:35 pm
BOS
-
PWM
1 stop6h 50m
Southwest
Deal found 6/8$398
This Southwest deal was found by Cheapflights users on 6/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:30 am
PWM
-
BOS
1 stop6h 40m
Southwest
Thu 7/95:45 am
BOS
-
PWM
1 stop4h 00m
Southwest
Deal found 6/7$407
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/28:22 pm
PWM
-
BOS
2 stops35h 26m
Multiple Airlines
Thu 7/910:04 am
BOS
-
PWM
1 stop23h 08m
Multiple Airlines
Deal found 6/4$427
This Southwest deal was found by Cheapflights users on 6/6. 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 7/205:35 am
PWM
-
BOS
1 stop4h 15m
Southwest
Mon 7/207:50 pm
BOS
-
PWM
1 stop4h 20m
Southwest
Deal found 6/6$447
This JetBlue deal was found by Cheapflights users on 6/6. 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.
Mon 6/222:30 pm
PWM
-
BOS
1 stop4h 04m
JetBlue
Tue 6/305:15 am
BOS
-
PWM
1 stop7h 15m
JetBlue
Deal found 6/6$453
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:01 pm
PWM
-
BOS
2 stops16h 08m
Multiple Airlines
Sat 7/118:37 am
BOS
-
PWM
1 stop7h 39m
Multiple Airlines
Deal found 6/6$472
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:59 am
PWM
-
BOS
1 stop9h 24m
American Airlines
Fri 7/32:04 pm
BOS
-
PWM
1 stop19h 18m
American Airlines
Deal found 6/7$503

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 June 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(JetBlue)

One-way from

$118
(Expedia)
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 June 9, 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

Fri 7/3

2:30 pm-6:49 pm

1 stop4h 19m

Boston Logan Intl

Sun 7/19

7:39 pm-12:16 am

1 stop4h 37m

$237

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 8/14

6:00 am-11:21 am

1 stop5h 21m

Boston Logan Intl

Sun 8/16

8:43 am-12:17 pm

1 stop3h 34m

$237

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 8/14

6:00 am-11:21 am

1 stop5h 21m

Boston Logan Intl

Mon 8/17

8:43 am-12:21 pm

1 stop3h 38m

$237

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 7/3

2:30 pm-6:49 pm

1 stop4h 19m

Boston Logan Intl

Fri 7/10

7:39 pm-12:16 am

1 stop4h 37m

$237

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 7/4

2:30 pm-6:49 pm

1 stop4h 19m

Boston Logan Intl

Sat 7/11

4:43 pm-12:16 am

1 stop7h 33m

$237
Quickest round-trip

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 7/4

2:30 pm-6:49 pm

1 stop4h 19m

Boston Logan Intl

Sun 7/5

8:43 am-12:30 pm

1 stop3h 47m

$271

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 6/26

6:00 am-11:35 am

1 stop5h 35m

Boston Logan Intl

Fri 7/3

4:40 pm-12:25 am

1 stop7h 45m

$294

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 7/6

6:00 am-11:37 am

1 stop5h 37m

Boston Logan Intl

Tue 7/7

8:41 am-12:30 pm

1 stop3h 49m

$348
Cheapest one-way

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 8/11

1:17 pm-5:15 pm

1 stop3h 58m

$118
Quickest one-way

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 7/2

6:00 am-9:45 am

1 stop3h 45m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/4

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 4h 19m. 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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