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$99+ Cheap flights from Portland to Boston (PDX - BOS)

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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Portland to Boston Logan Intl are usually found in January or May, booked 63 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap flight deals from Portland to Boston

Cheapest flights from Portland to Boston
Explore the most affordable flight options available from Portland to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 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 12/305:11 pmPDX - BOS
1 stop10h 31mDelta
Sat 1/106:10 amBOS - PDX
1 stop9h 22mDelta
Deal found 12/22$381
This United Airlines deal was found by Cheapflights users on 12/21. 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 12/309:00 amPDX - BOS
1 stop8h 42mUnited Airlines
Wed 1/76:00 amBOS - PDX
2 stops10h 45mUnited Airlines
Deal found 12/21$409
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 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.
Sun 12/285:11 pmPDX - BOS
1 stop10h 31mDelta
Thu 1/85:50 amBOS - PDX
1 stop9h 56mDelta
Deal found 12/22$476
This Delta deal was found by Cheapflights users on 12/21. 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.
Sun 12/285:30 amPDX - BOS
1 stop7h 38mDelta
Sun 1/46:10 amBOS - PDX
1 stop9h 50mDelta
Deal found 12/21$488

Find flight deals from Portland to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Boston (BOS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 23, 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 Boston Logan Intl
Search Deals
One-way flight from Portland to Boston Logan Intl
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 Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Portland to Boston Logan Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Boston 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 23, 2025.
Use the filters below to find and compare flights from Portland to Boston that are best for you.

Fly from

Portland

Fly to

Boston

Route

Depart

Return

Price

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 3/4

12:40 am-10:51 am

1 stop7h 11m

Boston Logan Intl

Sun 3/8

6:50 pm-11:58 pm

1 stop8h 08m

$218

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 1/5

11:45 pm-11:12 am

1 stop8h 27m

Boston Logan Intl

Sat 1/10

5:57 pm-12:42 am

1 stop9h 45m

$254

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sun 1/18

6:00 am-7:10 pm

1 stop10h 10m

Boston Logan Intl

Tue 1/20

5:50 am-12:46 pm

1 stop9h 56m

$258

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 1/22

6:30 am-5:10 pm

1 stop7h 40m

Boston Logan Intl

Wed 1/28

2:40 pm-10:15 pm

2 stops10h 35m

$266

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 1/15

6:30 am-9:23 pm

1 stop11h 53m

Boston Logan Intl

Tue 1/20

6:15 am-11:55 pm

2 stops20h 40m

$275

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 3/6

7:35 pm-6:50 am

1 stop8h 15m

Boston Logan Intl

Sun 3/8

6:50 pm-11:58 pm

1 stop8h 08m

$279

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 1/15

11:59 pm-1:13 pm

2 stops10h 14m

Boston Logan Intl

Tue 1/20

3:15 pm-9:12 pm

1 stop8h 57m

$280

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 5/20

11:40 pm-8:00 am

Nonstop5h 20m

Boston Logan Intl

Tue 5/26

7:05 pm-10:25 pm

Nonstop6h 20m

$282

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

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 1/28

11:59 am-11:45 pm

1 stop8h 46m

Boston Logan Intl

Sat 1/31

9:00 am-6:50 pm

2 stops12h 50m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 21 results
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Compare providers for flights from Portland to Boston

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Boston in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Portland-Boston flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland-Boston flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Portland-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Boston flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Boston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Portland to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston 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 Boston

How far ahead should I book a flight from Portland to Boston?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Boston. Price data was last updated on December 19, 2025.

The best time to book flights from Portland to Boston is 63 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Portland to Boston?

Currently, April is the cheapest month in which you can book a flight from Portland to Boston (average of $103). Flying from Portland to Boston 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 BOS?

Find hourly flight availability from Portland to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

A simple way to save on the total cost of your ticket is to fly from Portland to Boston at noon. If you’re flexible enough to do this you can expect to save up to 47% on your trip compared to booking a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from Portland to Boston. Price data was last updated on December 20, 2025.

Travelers seeking maximum savings on their Portland to Boston 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 Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated December 23, 2025.
See what other customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines from Portland to Boston have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,513 reviews

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

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
11,513 reviews
Alaska Airlines
8.0
Very good
11,513 reviews

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

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
8,013 reviews
Alaska Airlines
8.0
Very good
11,513 reviews

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

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
11,513 reviews

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

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
9,106 reviews
Alaska Airlines
8.0
Very good
11,513 reviews

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

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
2,898 reviews
Alaska Airlines
8.0
Very good
11,513 reviews

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

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 Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airports do I use to fly from Portland to Boston?

    Booking a flight from Portland (PDX) to Boston Logan Intl (BOS) is your only option if you wish to fly from Portland to Boston. On a typical day, there are 3 flights from Portland to Logan Intl, all of which are around 5h 20m for a nonstop flight. You can also purchase a plane ticket from 7 airlines when you book a flight from Portland to Boston.

  • How popular is this Portland to Boston flight route?

    Flights from Portland to Boston Logan Intl have been viewed 3 times in the past calendar month.

  • How long is the flight from Portland to Boston?

    Departing from Portland to Boston will take you 7h 11m. Portland and Boston are separated by a distance of 2528 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Portland to Boston round-trip?

    Delta, at $108, was found to be the cheapest airline from Portland to Boston.Alternate airlines to your destination round-trip include Hawaiian Airlines and JetBlue. Delta is priced at 71% lower than the current average price of a flight leaving 3 months from now.

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

    $79 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and JetBlue, with prices starting from $98 and $98, respectively.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Portland to Boston on time: Alaska Airlines (81%), Hawaiian Airlines (81%), Qatar Airways (81%).

  • What are the cheapest flights from Portland to Boston?

    Looking for the cheapest flight from Portland to Boston? While on average our users pay $405, our data indicates the cheapest price to be $138. The most popular route (Portland - Boston Logan Intl), is priced around $197.

  • Where are the most common layover locations when flying from Portland to Boston?

    Portland to Boston flights have a layover in Seattle most of the time. Minneapolis follows Seattle in terms of the most common layover location on Portland to Boston flights.

  • What are some popular things to do or see while on a layover in Seattle?

    Pike Place Market, Space Needle, and Seattle Waterfront are currently the most popular points of interest in Seattle at the moment. Those on a layover in Seattle interested in visiting Pike Place Market, Space Needle, or Seattle Waterfront can do so by traveling 11.2 mi, 12.0 mi, and 10.9 mi, respectively from Seattle/Tacoma Intl. Those landing in Seattle looking to spend some time exploring during their layover can rent a car for about $49 per day.

  • What are some popular points of interest to see during a layover in Minneapolis?

    Minneapolis Armory, Orpheum Theatre, and State Theatre are currently the most popular points of interest in Minneapolis at the moment. Minneapolis Armory, Orpheum Theatre and State Theatre are located about 7.0 mi, 7.3 mi, and 7.3 mi, respectively from Minneapolis St Paul if you are interested in checking them out. Those looking to explore during their layover in Minneapolis can rent a car from Minneapolis St Paul for about $49 per day.

  • Where are the least popular layover locations for Portland to Boston flights?

    Portland to Boston flights have a layover in Chicago least often.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Boston 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 Boston?

    Currently, April is the cheapest month in which you can book a flight from Portland to Boston (average of $103). Flying from Portland to Boston 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Brockton
Cranston
Lincoln
Lowell
Smithfield
Peabody
Quincy
York Beach
Warwick
Londonderry
Swansea
Old Orchard Beach
Waltham
Chelsea

Browse thousands of different options on Cheapflights for your next trip

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Top 7 airlines flying from Portland to Boston

Discover the top 7 airlines that operate flights from Portland to Boston. 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 23, 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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