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Massachusetts

$109+ Cheap flights from Portland (PDX) 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap flight deals from Portland to Massachusetts

Keep the following information in mind while searching for Portland to Massachusetts flight deals. Data was last updated July 3, 2025.

Round-trip from

$195
(SmartFares)

One-way from

$109
(Hawaiian Airlines)

Popular in

December

Cheapest in

September

Average price

$397

Good round-trip deal

$268 or less

Good one-way deal

$153 or less
From Portland to Massachusetts
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One-way flight from Portland to Massachusetts
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Highest demand for flights based on searches. 12% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Portland to Massachusetts.
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Price to beat on a one-way flight from Portland to Massachusetts.
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Find 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 July 3, 2025.

This SmartFares deal was found by Cheapflights users on 7/1. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/79:37 pmPDX - BOS
Nonstop5h 23mAlaska Airlines
Thu 8/146:00 amBOS - PDX
Nonstop6h 17mAlaska Airlines
Deal found 7/1$195
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 8/79:37 pmPDX - BOS
Nonstop5h 23mHawaiian Airlines
Thu 8/146:00 amBOS - PDX
Nonstop6h 17mHawaiian Airlines
Deal found 7/2$199
This JetBlue deal was found by Cheapflights users on 7/1. 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 8/1211:35 pmPDX - BOS
Nonstop5h 20mJetBlue
Wed 8/208:00 amBOS - PDX
Nonstop6h 11mJetBlue
Deal found 7/1$217
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Thu 8/711:12 pmPDX - BOS
1 stop9h 59mAmerican Airlines
Thu 8/142:33 pmBOS - PDX
1 stop11h 34mAmerican Airlines
Deal found 7/2$218
This Southwest deal was found by Cheapflights users on 7/2. 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 8/266:00 pmPDX - BOS
2 stops11h 10mSouthwest
Thu 9/412:15 pmBOS - PDX
1 stop7h 55mSouthwest
Deal found 7/2$222
This Delta deal was found by Cheapflights users on 7/2. 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.
Tue 8/197:05 pmPDX - BOS
1 stop8h 20mDelta
Tue 8/265:15 amBOS - PDX
1 stop8h 25mDelta
Deal found 7/2$237
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Sat 12/135:00 amPDX - BOS
2 stops9h 15mUnited Airlines
Sat 1/106:00 amBOS - PDX
1 stop8h 35mUnited Airlines
Deal found 7/1$242
This American Airlines deal was found by Cheapflights users on 7/3. 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 8/1911:59 pmPDX - ACK
2 stops12h 56mAmerican Airlines
Tue 8/264:25 pmACK - PDX
1 stop8h 39mAmerican Airlines
Deal found 7/3$246
This Mytrip deal was found by Cheapflights users on 7/3. 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 8/215:07 pmPDX - BOS
1 stop13h 42mAllegiant Air
Sun 8/2411:36 amBOS - PDX
2 stops23h 20mAllegiant Air
Deal found 7/3$275
This Orbitz deal was found by Cheapflights users on 7/2. 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.
Sat 7/197:01 pmPDX - BOS
2 stops9h 58mMultiple Airlines
Wed 7/306:00 amBOS - PDX
Nonstop6h 17mMultiple Airlines
Deal found 7/2$300
This FlightHub deal was found by Cheapflights users on 7/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/23:10 pmPDX - BOS
2 stops14h 27mSpirit Airlines
Sat 8/96:00 amBOS - PDX
2 stops30h 18mSpirit Airlines
Deal found 7/1$301
This Mytrip deal was found by Cheapflights users on 7/3. 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.
Fri 8/153:12 pmPDX - BDL
2 stops18h 28mMultiple Airlines
Sun 8/2412:16 pmBDL - PDX
2 stops22h 40mMultiple Airlines
Deal found 7/3$336

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 July 3, 2025.
Use the filters below to find and compare flights from Portland to Massachusetts that are best for you.

Fly from

Portland

Fly to

Massachusetts

Route

Depart

Return

Price

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 8/7

9:37 pm-6:00 am

Nonstop5h 23m

Boston Logan Intl

Thu 8/14

6:00 am-9:17 am

Nonstop6h 17m

$195

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 8/7

9:37 pm-6:00 am

Nonstop5h 23m

Boston Logan Intl

Thu 8/14

6:00 am-9:17 am

Nonstop6h 17m

$199

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 8/12

6:00 am-4:25 pm

1 stop7h 25m

Boston Logan Intl

Sun 8/24

5:30 am-10:15 am

1 stop7h 45m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 8/7

11:12 pm-12:11 pm

1 stop9h 59m

Boston Logan Intl

Thu 8/14

2:33 pm-11:07 pm

1 stop11h 34m

$218

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 8/19

7:05 pm-6:25 am

1 stop8h 20m

Boston Logan Intl

Tue 8/26

5:15 am-10:40 am

1 stop8h 25m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sat 12/13

5:00 am-5:15 pm

2 stops9h 15m

Boston Logan Intl

Sat 1/10

6:00 am-11:35 am

1 stop8h 35m

$242

PortlandNantucket

PDX - ACK

PDXACK

Portland

Tue 8/19

11:59 pm-3:55 pm

2 stops12h 56m

Nantucket Memorial

Tue 8/26

4:25 pm-10:04 pm

1 stop8h 39m

$246

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 8/20

12:21 pm-8:43 pm

Nonstop5h 22m

Boston Logan Intl

Mon 8/25

8:00 am-11:11 am

Nonstop6h 11m

$262

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 8/21

5:07 pm-9:49 am

1 stop13h 42m

Boston Logan Intl

Sun 8/24

11:36 am-7:56 am

2 stops23h 20m

$275

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sat 7/19

7:01 pm-7:59 am

2 stops9h 58m

Boston Logan Intl

Wed 7/30

6:00 am-9:17 am

Nonstop6h 17m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 59 results
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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 to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $218). Flying from Portland to Massachusetts in June is currently the most expensive (average of $306). 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.

What is the cheapest time of day to fly from PDX to MA?

Find hourly flight availability from Portland to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2025.

When flying from Portland to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Portland to Massachusetts

Explore weekly flight availability from Portland to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 3, 2025.

The most flights from PDX to USMA are scheduled on a Thursday (11 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated July 3, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Portland to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,270 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,970 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,545 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,845 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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?

    Most people fly from Portland (PDX) if they book a flight from Portland to Massachusetts. Portland is conveniently located just 6.0 mi from Portland’s city center.

  • How popular is this Portland to Massachusetts flight route?

    Flights from Portland to Massachusetts have been viewed 5 times in the past calendar month.

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

    To fly one-way, consider booking your trip with Hawaiian Airlines, which is currently one of the cheapest options available, starting at $109. Southwest flights start at $114 while deals on Alaska Airlines start at $118 one-way.

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

    While some choose either Portland - Albany Intl or Portland - Hartford Bradley Intl, Portland - Boston Logan Intl is the most popular route from Portland to Massachusetts.

  • What are the most reliable airlines from Portland to Massachusetts?

    No one likes to see their flight delayed. When booking a flight from Portland to Massachusetts consider choosing Condor (86%), JetBlue (60%) or Qatar Airways (58%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Portland to Massachusetts?

    On average you can expect to pay $434 for a flight from Portland to Massachusetts. The cheapest flight overall is $108 while the most popular route, (Portland - Boston Logan Intl) is currently priced at $210.

  • 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 to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $218). Flying from Portland to Massachusetts in June is currently the most expensive (average of $306). 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.

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Alternative routes for Portland to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Portland to Massachusetts

Discover the top 9 airlines that operate flights from Portland to Massachusetts. 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$77Average$223FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$125Average$348FlexibilityNo cancel feeOn-time85%
DeltaCheapest$131Average$328FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$153Average$334FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$180Average$470FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$206Average$416FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$222Average$446FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$427FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$255Average$486FlexibilityNo cancel feeOn-time75%

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