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Massachusetts

$115+ Cheap flights from Oregon 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find flight deals from Oregon to Massachusetts

Cheapest flights from Oregon to Massachusetts
Explore the most affordable flight options available from Oregon to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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.
Tue 11/1812:35 amPDX - BOS
1 stop7h 21mDelta
Sun 11/235:50 amBOS - PDX
1 stop9h 58mDelta
Deal found 10/28$218
This Southwest deal was found by Cheapflights users on 10/29. 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.
Wed 12/36:55 pmPDX - BOS
2 stops10h 20mSouthwest
Tue 12/91:35 pmBOS - PDX
1 stop8h 45mSouthwest
Deal found 10/29$233
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2711:12 pmPDX - BOS
1 stop10h 16mUnited Airlines
Thu 12/46:00 amBOS - PDX
1 stop8h 48mUnited Airlines
Deal found 10/28$237
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 11/1912:35 amPDX - BOS
1 stop7h 21mDelta
Sun 11/235:50 amBOS - PDX
1 stop9h 58mDelta
Deal found 10/28$238
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:05 pmPDX - BOS
1 stop10h 20mDelta
Mon 11/177:00 pmBOS - PDX
1 stop8h 14mDelta
Deal found 10/27$239
This Southwest deal was found by Cheapflights users on 10/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:55 pmPDX - BOS
2 stops10h 20mSouthwest
Thu 12/111:35 pmBOS - PDX
1 stop8h 45mSouthwest
Deal found 10/27$254
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:55 amPDX - BOS
1 stop7h 10mSouthwest
Wed 12/176:45 amBOS - PDX
1 stop15h 05mSouthwest
Deal found 10/28$258
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1111:59 pmPDX - BOS
1 stop7h 35mUnited Airlines
Sun 11/166:00 amBOS - PDX
1 stop11h 46mUnited Airlines
Deal found 10/28$259
This Delta deal was found by Cheapflights users on 10/28. 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 11/1012:35 amPDX - BOS
1 stop7h 22mDelta
Sun 11/167:15 amBOS - PDX
1 stop11h 18mDelta
Deal found 10/28$261
This Southwest deal was found by Cheapflights users on 10/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:00 amPDX - BOS
1 stop11h 45mSouthwest
Wed 12/1012:20 pmBOS - PDX
2 stops12h 40mSouthwest
Deal found 10/27$264
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1512:35 amPDX - BOS
1 stop7h 22mDelta
Tue 11/1810:20 amBOS - PDX
1 stop11h 07mDelta
Deal found 10/27$268
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:15 amPDX - BOS
1 stop7h 30mSouthwest
Sat 1/245:30 amBOS - PDX
2 stops12h 05mSouthwest
Deal found 10/28$269

Cheap flight deals from Oregon to Massachusetts

Keep the following information in mind while searching for Oregon to Massachusetts flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$218
(Delta)

One-way from

$115
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$434

Good round-trip deal

$447 or less

Good one-way deal

$258 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 Oregon to Massachusetts
Search Deals
One-way flight from Oregon to Massachusetts
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Oregon to Massachusetts.
Search Deals
Price to beat on a one-way flight from Oregon to Massachusetts.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon 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 October 29, 2025.
Use the filters below to find and compare flights from Oregon to Massachusetts that are best for you.

Fly from

Oregon

Fly to

Massachusetts

Route

Depart

Return

Price

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 11/19

6:00 am-5:08 pm

1 stop8h 08m

Boston Logan Intl

Sun 11/23

5:50 am-12:48 pm

1 stop9h 58m

$218

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 11/12

12:35 am-10:57 am

1 stop7h 22m

Boston Logan Intl

Mon 11/17

7:00 pm-12:14 am

1 stop8h 14m

$261

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 12/12

6:30 am-5:40 pm

1 stop8h 10m

Boston Logan Intl

Mon 12/15

1:35 pm-10:35 pm

2 stops12h 00m

$280

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 12/4

5:50 pm-3:37 pm

1 stop18h 47m

Boston Logan Intl

Sat 12/6

4:40 pm-8:10 pm

Nonstop6h 30m

$290

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 12/5

10:50 am-10:45 pm

1 stop8h 55m

Boston Logan Intl

Sat 12/6

9:20 am-4:30 pm

2 stops10h 10m

$309

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 11/19

7:00 am-3:24 pm

Nonstop5h 24m

Boston Logan Intl

Sun 11/23

5:28 pm-8:49 pm

Nonstop6h 21m

$317

BoiseBoston

BOI - BOS

BOIBOS

Boise Air Term. Gowen Fld

Tue 3/10

7:00 am-6:09 pm

1 stop9h 09m

Boston Logan Intl

Wed 3/11

7:00 am-1:45 pm

1 stop8h 45m

$318

BoiseBoston

BOI - BOS

BOIBOS

Boise Air Term. Gowen Fld

Tue 3/10

1:10 pm-11:54 pm

1 stop8h 44m

Boston Logan Intl

Wed 3/11

11:00 am-6:25 pm

1 stop9h 25m

$319

RedmondBoston

RDM - BOS

RDMBOS

Bend/Redmond

Tue 1/13

1:34 pm-11:59 pm

1 stop7h 25m

Boston Logan Intl

Tue 1/20

5:20 pm-10:46 pm

1 stop8h 26m

$327

MedfordBoston

MFR - BOS

MFRBOS

Medford

Tue 3/10

11:45 am-11:59 pm

1 stop9h 14m

Boston Logan Intl

Wed 3/11

5:55 pm-12:09 am

1 stop9h 14m

$336

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 60 results
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Best time to book a flight from Oregon to Massachusetts

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

What is the cheapest month to book a flight from Oregon to Massachusetts?

Currently, April is the cheapest month in which you can book a flight from Oregon to Massachusetts (average of $103). Flying from Oregon to Massachusetts in December is currently the most expensive (average of $255). 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 OR to MA?

Find hourly flight availability from Oregon 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 October 29, 2025.

It’s typically best to fly out from Oregon to Massachusetts in the afternoon. Doing so could potentially save you 12% on the flight price compared to flying at noon, which is usually more expensive.

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

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

Travelers seeking maximum savings on their Oregon to Massachusetts flight should consider departing on Saturday afternoons when fares are most often at their lowest. Saturday 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 October 29, 2025.
See what other customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines from Oregon to Massachusetts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,206 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,206 reviews
Alaska Airlines
8.0
Very good
11,206 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,994 reviews
Alaska Airlines
8.0
Very good
11,206 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,794 reviews
Alaska Airlines
8.0
Very good
11,206 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
9,001 reviews
Alaska Airlines
8.0
Very good
11,206 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
JetBlue
7.2
Good
2,907 reviews
Alaska Airlines
8.0
Very good
11,206 reviews

Comfort

7.8

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How popular is this Oregon to Massachusetts flight route?

    The Oregon to Massachusetts flight path was viewed by 4 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Oregon to Massachusetts?

    Airlines like Delta, Southwest, and Alaska Airlines fly from Oregon to Massachusetts in about 8h 08m. The time it takes to get you to your destination can typically vary by up to 10h 39m. Airlines will cover a distance of 2528 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airlines for a one-way flight from Oregon to Massachusetts are United Airlines ($120), Delta ($120), and Alaska Airlines ($158).

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oregon 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 Oregon to Massachusetts?

    Currently, April is the cheapest month in which you can book a flight from Oregon to Massachusetts (average of $103). Flying from Oregon to Massachusetts in December is currently the most expensive (average of $255). 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 Oregon 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 Oregon to Massachusetts

Discover the top 7 airlines that operate flights from Oregon 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$122Average$427FlexibilityNo cancel feeOn-time85%
DeltaCheapest$129Average$460FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$136Average$299FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$476FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$208Average$414FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$545FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$255Average$530FlexibilityNo cancel feeOn-time75%

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