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Massachusetts

$99+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
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 December 26, 2025.

This United Airlines deal was found by Cheapflights users on 12/22. 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 12/296:27 pmPDX - BOS
1 stop8h 31mUnited Airlines
Thu 1/85:57 pmBOS - PDX
1 stop9h 42mUnited Airlines
Deal found 12/22$368
This Southwest deal was found by Cheapflights users on 12/23. 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 12/295:00 amPDX - BOS
1 stop11h 20mSouthwest
Mon 1/56:55 pmBOS - PDX
1 stop8h 25mSouthwest
Deal found 12/23$373
This Delta deal was found by Cheapflights users on 12/22. 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 12/301:45 pmPDX - BOS
1 stop7h 39mDelta
Wed 1/75:50 amBOS - PDX
1 stop9h 56mDelta
Deal found 12/22$381
This Southwest deal was found by Cheapflights users on 12/23. 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 12/305:00 amPDX - BOS
2 stops10h 15mSouthwest
Tue 1/64:50 pmBOS - PDX
1 stop8h 25mSouthwest
Deal found 12/23$424
This Southwest deal was found by Cheapflights users on 12/23. 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.
Sun 12/285:30 amPDX - BOS
1 stop9h 55mSouthwest
Mon 1/56:55 pmBOS - PDX
1 stop8h 25mSouthwest
Deal found 12/23$459
This Southwest deal was found by Cheapflights users on 12/23. 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.
Wed 12/246:05 amPDX - BOS
1 stop7h 00mSouthwest
Mon 2/24:50 pmBOS - PDX
1 stop8h 25mSouthwest
Deal found 12/23$468
This United Airlines deal was found by Cheapflights users on 12/22. 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 12/307:30 amPDX - BOS
1 stop9h 26mUnited Airlines
Tue 1/69:30 amBOS - PDX
2 stops15h 19mUnited Airlines
Deal found 12/22$473
This Delta deal was found by Cheapflights users on 12/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:45 pmPDX - BOS
1 stop7h 39mDelta
Fri 1/95:35 pmBOS - PDX
1 stop8h 19mDelta
Deal found 12/25$476
This Travelocity deal was found by Cheapflights users on 12/23. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:26 pmPDX - BOS
1 stop11h 57mMultiple Airlines
Mon 2/25:20 pmBOS - PDX
Nonstop6h 28mMultiple Airlines
Deal found 12/23$490
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/298:45 pmPDX - BDL
1 stop30h 30mMultiple Airlines
Mon 1/57:00 amBDL - PDX
2 stops15h 50mMultiple Airlines
Deal found 12/25$661
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:29 pmPDX - BDL
1 stop12h 31mMultiple Airlines
Mon 1/57:00 amBDL - PDX
2 stops15h 50mMultiple Airlines
Deal found 12/25$695
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/298:45 pmPDX - BDL
1 stop30h 30mMultiple Airlines
Fri 1/27:00 amBDL - PDX
2 stops15h 50mMultiple Airlines
Deal found 12/25$698

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 December 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(American Airlines)

One-way from

$99
(Delta)

Popular in

December

Cheapest in

January

Average price

$556

Good round-trip deal

$427 or less

Good one-way deal

$168 or less
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
Highest demand for flights based on searches. 12% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Portland to Massachusetts.
Search Deals
Price to beat on a 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 December 26, 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

Fri 1/23

11:59 pm-1:20 pm

2 stops10h 21m

Boston Logan Intl

Sat 1/24

4:05 pm-9:49 pm

1 stop8h 44m

$236

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sun 3/8

11:59 pm-10:49 am

1 stop7h 50m

Boston Logan Intl

Thu 3/12

5:45 am-12:33 pm

1 stop9h 48m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 1/9

6:00 am-7:10 pm

1 stop10h 10m

Boston Logan Intl

Fri 1/16

6:45 pm-12:17 am

1 stop8h 32m

$241

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sat 1/24

10:47 am-11:49 pm

2 stops10h 02m

Boston Logan Intl

Thu 1/29

4:16 pm-10:32 pm

1 stop9h 16m

$242

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 1/14

7:00 am-5:19 pm

1 stop7h 19m

Boston Logan Intl

Wed 1/21

9:30 am-6:10 pm

2 stops11h 40m

$242

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sun 1/18

6:00 am-7:10 pm

1 stop10h 10m

Boston Logan Intl

Fri 1/23

1:30 pm-10:45 pm

1 stop12h 15m

$258

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 1/9

11:05 am-10:30 pm

1 stop8h 25m

Boston Logan Intl

Wed 1/14

4:50 pm-10:15 pm

1 stop8h 25m

$259

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 1/9

6:30 am-5:10 pm

1 stop7h 40m

Boston Logan Intl

Sun 1/11

5:20 am-10:45 am

1 stop8h 25m

$259

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 1/19

12:40 am-4:55 pm

2 stops13h 15m

Boston Logan Intl

Fri 1/23

5:35 pm-11:55 pm

1 stop9h 20m

$275

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 1/30

5:15 pm-6:05 am

2 stops9h 50m

Boston Logan Intl

Mon 2/2

12:45 pm-10:20 pm

1 stop12h 35m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 48 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, April is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $103). Flying from Portland to Massachusetts in March is currently the most expensive (average of $229). 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 December 26, 2025.

It’s typically best to fly out from Portland to Massachusetts at noon. Doing so could potentially save you 58% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Portland to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Portland to Massachusetts. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland to Massachusetts flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 December 26, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines 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
11,534 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Alaska Airlines
8.0
Very good
11,534 reviews
Alaska Airlines
8.0
Very good
11,534 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Delta
7.9
Good
8,014 reviews
Alaska Airlines
8.0
Very good
11,534 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Hawaiian Airlines
7.8
Good
2,820 reviews
Alaska Airlines
8.0
Very good
11,534 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
United Airlines
7.4
Good
9,115 reviews
Alaska Airlines
8.0
Very good
11,534 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
JetBlue
7.2
Good
2,900 reviews
Alaska Airlines
8.0
Very good
11,534 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.

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 3 times in the past calendar month.

  • How long is the flight from Portland to Massachusetts?

    Airlines like United Airlines, Delta, and American Airlines fly from Portland to Massachusetts in about 8h 57m. The time it takes to get you to your destination can typically vary by up to 1h 24m. Portland and Massachusetts are separated by a distance of 2461 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $79. Delta flights start at $98 while deals on JetBlue start at $98 one-way.

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

    While some choose either Portland - Hartford Bradley Intl or Portland - Albany 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 Alaska Airlines (81%), Hawaiian Airlines (81%) or Qatar Airways (81%) 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 $405 for a flight from Portland to Massachusetts. The cheapest flight overall is $138 while the most popular route, (Portland - Boston Logan Intl) is currently priced at $197.

  • 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, April is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $103). Flying from Portland to Massachusetts in March is currently the most expensive (average of $229). 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

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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 7 airlines flying from Portland to Massachusetts

Discover the top 7 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 December 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$122Average$360FlexibilityNo cancel feeOn-time85%
DeltaCheapest$124Average$297FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$130Average$295FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$280FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$206Average$403FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$400FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$257Average$479FlexibilityNo cancel feeOn-time75%

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