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$99+ Cheap flights from Massachusetts to Portland, ME (PWM)

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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PWM
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Massachusetts to Portland

Keep the following information in mind while searching for Massachusetts to Portland flight deals. Data was last updated July 31, 2025.

Round-trip from

$184
(Bravofly)

One-way from

$99
(Southwest)
From Massachusetts to Portland
Search Deals
One-way flight from Massachusetts to Portland
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Find flight deals from Massachusetts to Portland

Cheapest flights from Massachusetts to Portland
Explore the most affordable flight options available from Massachusetts to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Bravofly deal was found by Cheapflights users on 7/30. 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/227:40 pmBOS - PWM
1 stop4h 37mJetBlue
Thu 8/286:10 amPWM - BOS
1 stop3h 41mJetBlue
Deal found 7/30$184
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/303:40 pmBDL - PWM
1 stop6h 20mSouthwest
Sat 9/65:45 amPWM - BDL
1 stop6h 15mSouthwest
Deal found 7/29$197
This Southwest deal was found by Cheapflights users on 7/30. 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.
Sat 11/85:20 amALB - PWM
1 stop6h 45mSouthwest
Tue 11/115:30 amPWM - ALB
1 stop6h 35mSouthwest
Deal found 7/30$224
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 9/138:00 amBOS - PWM
1 stop8h 50mAmerican Airlines
Sat 9/208:40 amPWM - BOS
1 stop34h 19mAmerican Airlines
Deal found 7/30$302
This Expedia deal was found by Cheapflights users on 7/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/267:12 amBDL - PWM
1 stop6h 11mJetBlue
Tue 9/22:19 pmPWM - BDL
1 stop9h 27mJetBlue
Deal found 7/29$308
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 8/3012:09 pmBDL - PWM
1 stop9h 36mAmerican Airlines
Sat 9/68:40 amPWM - BDL
2 stops11h 40mAmerican Airlines
Deal found 7/29$385
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/151:54 pmALB - PWM
1 stop21h 00mDelta
Fri 9/194:55 pmPWM - ALB
1 stop23h 51mDelta
Deal found 7/28$395
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 9/1912:36 pmALB - PWM
2 stops11h 09mAmerican Airlines
Mon 9/227:05 amPWM - ALB
2 stops9h 54mAmerican Airlines
Deal found 7/29$468
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/182:53 pmBOS - PWM
1 stop18h 13mMultiple Airlines
Mon 9/229:46 amPWM - BOS
2 stops13h 24mMultiple Airlines
Deal found 7/29$490
This United Airlines deal was found by Cheapflights users on 7/29. 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 8/265:30 amBOS - PWM
2 stops17h 33mUnited Airlines
Tue 9/26:23 pmPWM - BOS
1 stop18h 25mUnited Airlines
Deal found 7/29$519
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Mon 9/86:00 amALB - PWM
3 stops17h 03mUnited Airlines
Fri 9/126:14 amPWM - ALB
1 stop8h 51mUnited Airlines
Deal found 7/30$526
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1611:30 amBDL - PWM
3 stops24h 21mMultiple Airlines
Wed 8/208:07 pmPWM - BDL
2 stops27h 16mMultiple Airlines
Deal found 7/29$540

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Portland 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 July 31, 2025.
Use the filters below to find and compare flights from Massachusetts to Portland that are best for you.

Fly from

Massachusetts

Fly to

Portland

Route

Depart

Return

Price

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Fri 8/22

7:40 pm-12:17 am

1 stop4h 37m

Portland

Thu 8/28

6:10 am-9:51 am

1 stop3h 41m

$184

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Sat 8/30

3:40 pm-10:00 pm

1 stop6h 20m

Portland

Sat 9/6

5:45 am-12:00 pm

1 stop6h 15m

$197

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Wed 9/17

5:50 am-9:50 am

1 stop4h 00m

Portland

Sat 9/20

5:45 am-12:00 pm

1 stop6h 15m

$262

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Sat 9/13

8:00 am-4:50 pm

1 stop8h 50m

Portland

Sat 9/20

8:40 am-6:59 pm

1 stop34h 19m

$302

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Tue 8/26

7:12 am-1:23 pm

1 stop6h 11m

Portland

Tue 9/2

2:19 pm-11:46 pm

1 stop9h 27m

$308

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Sat 8/30

12:09 pm-9:45 pm

1 stop9h 36m

Portland

Sat 9/6

8:40 am-8:20 pm

2 stops11h 40m

$385

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Mon 9/15

1:54 pm-10:54 am

1 stop21h 00m

Portland

Fri 9/19

4:55 pm-4:46 pm

1 stop23h 51m

$395

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Fri 9/19

12:36 pm-11:45 pm

2 stops11h 09m

Portland

Mon 9/22

7:05 am-4:59 pm

2 stops9h 54m

$468

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Thu 9/18

2:53 pm-9:06 am

1 stop18h 13m

Portland

Mon 9/22

9:46 am-11:10 pm

2 stops13h 24m

$490

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Tue 8/26

5:30 am-11:03 pm

2 stops17h 33m

Portland

Tue 9/2

6:23 pm-12:48 pm

1 stop18h 25m

$519

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 31 results
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Best time to book a flight from Massachusetts to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Massachusetts 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 Massachusetts to Portland

What is the cheapest month to book a flight from Massachusetts to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Portland, Maine (average of $296). Flying from Massachusetts to Portland, Maine in July is currently the most expensive (average of $394). 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.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated July 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Breeze Airways from Massachusetts to Portland to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
191 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,902 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Portland. 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 into for flights to Portland from Massachusetts?

    Portland (PWM), located 2.9 mi from the city center, is the airport you fly into when you book flights from Massachusetts to Portland.

  • What are the cheapest airlines to fly from Massachusetts to Portland, Maine one-way?

    The cheapest airlines for a one-way flight from Massachusetts to Portland, Maine are Southwest ($99), JetBlue ($102), and American Airlines ($167).

  • What are the most popular routes from Massachusetts to Portland, Maine?

    The most popular route from Massachusetts to Portland, Maine is Hartford Bradley Intl - Portland. You may also consider Boston Logan Intl - Portland or Albany Intl - Portland.

  • Can I find deals for flights from Massachusetts to Portland that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Portland.

  • Can I find deals for business class flights from Massachusetts to Portland?

    Yes. Cheapflights offers flight deals from Massachusetts to Portland 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 Massachusetts to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Portland, Maine (average of $296). Flying from Massachusetts to Portland, Maine in July is currently the most expensive (average of $394). 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

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Brunswick
North Conway
Auburn
Conway
Lewiston

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Alternative routes for Massachusetts to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Massachusetts to Portland

Discover the top airline that operate flights from Massachusetts to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$151Average$236FlexibilityNo cancel feeOn-time62%

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