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Massachusetts

$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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
May 29 — Jun 51
Fri 5/29
Fri 6/5
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 April 29, 2026.

This Flysmarter deal was found by Cheapflights users on 4/29. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:00 am
PWM
-
BOS
1 stop5h 02m
JetBlue
Wed 5/276:40 pm
BOS
-
PWM
1 stop5h 18m
JetBlue
Deal found 4/29$223
This Priceline deal was found by Cheapflights users on 4/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:00 am
PWM
-
BOS
1 stop5h 02m
JetBlue
Sat 5/233:55 pm
BOS
-
PWM
1 stop8h 03m
JetBlue
Deal found 4/27$227
This JetBlue deal was found by Cheapflights users on 4/26. 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 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 4/26$261
This Orbitz deal was found by Cheapflights users on 4/25. 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 Orbitz 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
Sat 5/303:55 pm
BOS
-
PWM
1 stop8h 03m
JetBlue
Deal found 4/25$280
This Priceline deal was found by Cheapflights users on 4/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/132:30 pm
PWM
-
BOS
1 stop4h 04m
JetBlue
Sun 6/148:14 pm
BOS
-
PWM
1 stop4h 11m
JetBlue
Deal found 4/26$294
This Expedia deal was found by Cheapflights users on 4/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
PWM
-
BOS
1 stop5h 02m
JetBlue
Sun 5/315:20 am
BOS
-
PWM
1 stop8h 10m
JetBlue
Deal found 4/26$298
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/133:39 pm
PWM
-
BOS
1 stop7h 15m
American Airlines
Sat 5/1610:00 am
BOS
-
PWM
1 stop5h 07m
American Airlines
Deal found 4/29$313
This JetBlue deal was found by Cheapflights users on 4/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:20 am
PWM
-
BOS
1 stop7h 08m
JetBlue
Sat 5/165:25 pm
BOS
-
PWM
1 stop5h 38m
JetBlue
Deal found 4/27$333
This Expedia deal was found by Cheapflights users on 4/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:00 am
PWM
-
BOS
1 stop8h 50m
JetBlue
Mon 6/13:52 pm
BOS
-
PWM
1 stop8h 06m
JetBlue
Deal found 4/27$335

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 April 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$227
(Priceline)

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 April 29, 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

Thu 5/21

6:00 am-11:02 am

1 stop5h 02m

Boston Logan Intl

Sat 5/23

3:55 pm-11:58 pm

1 stop8h 03m

$227
Quickest round-trip

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

$261

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 5/13

3:39 pm-10:54 pm

1 stop7h 15m

Boston Logan Intl

Sat 5/16

10:00 am-3:07 pm

1 stop5h 07m

$313

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 5/13

3:39 pm-7:22 am

1 stop15h 43m

Boston Logan Intl

Sun 5/17

6:00 am-9:54 am

1 stop3h 54m

$313

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 5/12

7:20 am-2:28 pm

1 stop7h 08m

Boston Logan Intl

Sat 5/16

5:25 pm-11:03 pm

1 stop5h 38m

$333

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 5/9

7:20 am-2:28 pm

1 stop7h 08m

Boston Logan Intl

Sun 5/10

5:02 pm-11:02 pm

1 stop6h 00m

$333

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 5/25

6:00 am-2:50 pm

1 stop8h 50m

Boston Logan Intl

Mon 6/1

3:52 pm-11:58 pm

1 stop8h 06m

$335

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 10/14

5:50 am-12:40 pm

1 stop6h 50m

Boston Logan Intl

Mon 10/26

2:40 pm-9:55 pm

1 stop7h 15m

$347

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 5/23

6:00 am-3:16 pm

1 stop9h 16m

Boston Logan Intl

Sat 5/30

6:45 pm-11:58 pm

1 stop5h 13m

$372

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 5/23

9:52 am-9:42 pm

1 stop11h 50m

Boston Logan Intl

Sat 5/30

12:01 pm-7:16 pm

2 stops31h 15m

$378

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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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