$190+ Cheap flights from Portland to Boston (PDX - BOS)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Nov 8 — Nov 151
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Boston with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Portland to Boston Logan Intl are usually found in January or May, booked 39 days in advance, depart on a Friday or Thursday and return on a Wednesday
Cheap flight deals from Portland to Boston
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to BostonExplore 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 October 9, 2026.
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 October 9, 2026.
This Southwest deal was found by Cheapflights users on 10/7. 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 12/110:10 am -
2 stops9h 05m
Fri 12/44:40 pm -
1 stop8h 35m
Deal found 10/7![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 10/7. 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 10/278:45 pm -
2 stops15h 50m
Fri 10/304:50 pm -
1 stop10h 25m
Deal found 10/7![Southwest logo]()
$336
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Mon 12/218:00 am -
1 stop7h 14m
Tue 1/56:00 am -
1 stop10h 46m
Deal found 10/6![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/6. 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 11/198:00 am -
1 stop10h 10m
Tue 12/14:00 pm -
1 stop9h 01m
Deal found 10/6![American Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 10/6. 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 10/306:09 pm -
1 stop8h 38m
Fri 11/65:43 am -
1 stop9h 45m
Deal found 10/6![American Airlines logo]()
$342
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Wed 11/411:30 pm -
1 stop6h 53m
Sun 11/87:10 am -
1 stop10h 27m
Deal found 10/8![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 10/4. 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 10/2912:50 pm -
1 stop9h 25m
Sun 11/15:00 am -
1 stop8h 40m
Deal found 10/4![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 10/7. 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 11/411:40 am -
1 stop9h 05m
Wed 11/111:20 pm -
2 stops13h 05m
Deal found 10/7![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 10/7. 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 11/46:55 am -
2 stops12h 00m
Sat 11/78:00 am -
1 stop13h 00m
Deal found 10/7![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 10/5. 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 12/1510:15 am -
2 stops10h 25m
Mon 1/45:10 pm -
2 stops11h 10m
Deal found 10/5![Southwest logo]()
$350
Best flights from Portland to BostonDiscover carefully curated flight deals from Portland to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 9, 2026.
Discover carefully curated flight deals from Portland to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 9, 2026.
This Southwest deal was found by Cheapflights users on 10/5. 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 12/156:00 am -
2 stops10h 00m
Mon 1/44:20 pm -
1 stop10h 35m
Deal found 10/5![Southwest logo]()
$344
This Alaska Airlines deal was found by Cheapflights users on 10/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/257:00 am -
Nonstop5h 27m
Mon 3/15:45 pm -
1 stop18h 53m
Deal found 10/7![Alaska Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 10/7. 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 11/255:29 pm -
1 stop8h 59m
Fri 11/277:50 am -
1 stop27h 46m
Deal found 10/7![Delta logo]()
$470
This Southwest deal was found by Cheapflights users on 10/8. 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 12/2811:30 pm -
1 stop8h 30m
Fri 1/17:10 am -
1 stop8h 25m
Deal found 10/8![Southwest logo]()
$413
This Alaska Airlines deal was found by Cheapflights users on 10/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:03 am -
Nonstop5h 27m
Mon 11/96:09 pm -
1 stop18h 34m
Deal found 10/8![Alaska Airlines logo]()
$453
This Southwest deal was found by Cheapflights users on 10/4. 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 1/66:50 am -
2 stops8h 35m
Tue 1/124:55 pm -
1 stop8h 25m
Deal found 10/4![Southwest logo]()
$422
This Alaska Airlines deal was found by Cheapflights users on 10/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:03 am -
Nonstop5h 27m
Thu 11/124:33 pm -
Nonstop6h 20m
Deal found 10/7![Alaska Airlines logo]()
$467
This Southwest deal was found by Cheapflights users on 10/5. 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 12/1311:30 pm -
2 stops9h 50m
Thu 12/1712:45 pm -
2 stops11h 15m
Deal found 10/5![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 10/4. 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 1/76:50 am -
2 stops8h 35m
Tue 1/125:05 am -
2 stops12h 05m
Deal found 10/4![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 10/6. 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 11/46:55 am -
2 stops12h 00m
Mon 11/92:25 pm -
2 stops12h 30m
Deal found 10/6![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 10/4. 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.
Fri 10/3011:35 pm -
2 stops9h 55m
Mon 11/22:25 pm -
2 stops12h 30m
Deal found 10/4![Southwest logo]()
$462
Last-minute flights from Portland to BostonDiscover last-minute flight deals from Portland to Boston. Data last updated October 9, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Boston. Data last updated October 9, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/7. 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 10/278:45 pm -
2 stops15h 50m
Fri 10/304:50 pm -
1 stop10h 25m
Deal found 10/7![Southwest logo]()
$336
This American Airlines deal was found by Cheapflights users on 10/6. 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 10/2710:55 pm -
1 stop7h 42m
Sun 11/14:00 pm -
1 stop8h 59m
Deal found 10/6![American Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 10/4. 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 10/2912:50 pm -
1 stop9h 25m
Sun 11/15:00 am -
1 stop8h 40m
Deal found 10/4![Southwest logo]()
$344
This American Airlines deal was found by Cheapflights users on 10/6. 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 10/306:09 pm -
1 stop8h 38m
Fri 11/65:43 am -
1 stop9h 45m
Deal found 10/6![American Airlines logo]()
$342
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Wed 11/411:30 pm -
1 stop6h 53m
Sun 11/87:10 am -
1 stop10h 27m
Deal found 10/8![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 10/7. 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 11/411:40 am -
1 stop9h 05m
Wed 11/111:20 pm -
2 stops13h 05m
Deal found 10/7![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 10/7. 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 11/46:55 am -
2 stops12h 00m
Sat 11/78:00 am -
1 stop13h 00m
Deal found 10/7![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 10/5. 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 11/71:10 pm -
2 stops15h 55m
Sat 11/148:00 am -
1 stop13h 00m
Deal found 10/5![Southwest logo]()
$355
This American Airlines deal was found by Cheapflights users on 10/5. 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.
Wed 11/185:14 am -
1 stop8h 31m
Sat 11/211:30 pm -
1 stop11h 40m
Deal found 10/5![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/6. 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 11/198:00 am -
1 stop10h 10m
Tue 12/14:00 pm -
1 stop9h 01m
Deal found 10/6![American Airlines logo]()
$341
One-way flights from Portland to BostonSearch for one-way flight options from Portland to Boston. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
Search for one-way flight options from Portland to Boston. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:52 pm -
1 stop19h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Alaska Airlines logo]()
$190
This Alaska Airlines deal was found by Cheapflights users on 10/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:00 am -
1 stop31h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Alaska Airlines logo]()
$193
This United Airlines deal was found by Cheapflights users on 10/6. 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 1/57:00 am -
2 stops13h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![United Airlines logo]()
$194
This United Airlines deal was found by Cheapflights users on 10/7. 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 12/3111:42 pm -
2 stops9h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![United Airlines logo]()
$195
This Southwest deal was found by Cheapflights users on 10/5. 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.
Fri 11/1311:30 pm -
1 stop8h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Southwest logo]()
$196
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Wed 11/411:30 pm -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![United Airlines logo]()
$200
This United Airlines deal was found by Cheapflights users on 10/4. 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.
Fri 11/67:00 am -
1 stop11h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![United Airlines logo]()
$204
This United Airlines deal was found by Cheapflights users on 10/8. 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 11/37:26 pm -
2 stops14h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![United Airlines logo]()
$205
This American Airlines deal was found by Cheapflights users on 10/8. 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 11/198:00 am -
1 stop10h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![American Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 10/6. 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.
Fri 12/256:00 am -
2 stops10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Southwest logo]()
$210
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Sun 12/65:00 am -
2 stops9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![United Airlines logo]()
$214
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 October 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $330 (Southwest) |
One-way from | $190 (Alaska Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $468 |
Good round-trip deal | $482 or less |
Good one-way deal | $233 or less |
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 7,457,451 searches. Data last updated October 9, 2026.
Use the filters below to find and compare flights from Portland to Boston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Fri 12/25
7:00 am-9:05 pm
1 stop11h 05m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$200
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Tue 12/8
3:44 pm-10:19 am
2 stops15h 35m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$205
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sun 4/4
10:55 pm-9:04 am
1 stop7h 09m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$219
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Thu 1/21
6:00 am-4:42 pm
1 stop7h 42m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$219
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Fri 1/8
6:00 am-4:42 pm
1 stop7h 42m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$219
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Thu 11/5
5:15 pm-6:25 am
1 stop10h 10m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$219
Quickest round-trip
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Thu 1/7
7:27 am-3:53 pm
Nonstop5h 26m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$234
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Mon 1/11
7:27 am-3:53 pm
Nonstop5h 26m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$234
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Mon 1/4
9:50 pm-6:20 am
Nonstop5h 30m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$234
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Fri 12/18
11:59 pm-10:57 pm
1 stop19h 58m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$238
Showing 1-10 of 23 resultsSorted by cheapest first
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Portland-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Boston flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.
PDX-BOS
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
Prices
Airlines
More
How far ahead should I book a flight from Portland to Boston?
The best time to book flights from Portland to Boston is 90 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, January is the cheapest month in which you can book a flight from Portland to Boston (average of $322). Flying from Portland to Boston in December is currently the most expensive (average of $528). 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 October 9, 2026.
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 32% on your trip compared to booking a flight in the morning.
What’s the top layover airport for flights from Portland to Boston?
Share of 1-stop round-trip flights from Portland to Boston chosen by Cheapflights users in the past 12 months, using the same layover each way.
Chicago (ORD) – chosen by Cheapflights users on 50% of 1-stop itineraries from Portland to Boston on Cheapflights.
What’s the cheapest layover airport for flights from Portland to Boston?
Average round-trip fare for 1-stop flights from Portland to Boston, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Minneapolis (MSP) is the most affordable 1-stop option, with an average round-trip price of $164.
What’s the fastest layover option from Portland to Boston?
Shortest average travel time for 1-stop one-way flights from Portland to Boston, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 7h 09m.
Which airport typically offers the quickest layover for flights from Portland to Boston?
Average layover duration for 1-stop one-way flights from Portland to Boston, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Chicago (ORD) offer the fastest connection on this route, with an average layover time of 0h 46m.
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 October 9, 2026.
See what other customers who have flown with Alaska Airlines,Delta, andUnited 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.
Comfort
7.8
Overall
7.9
Entertainment
7.0
Crew
8.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Comfort
7.8
Overall
7.9
Entertainment
7.0
Crew
8.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Comfort
7.8
Overall
7.9
Entertainment
7.0
Crew
8.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Comfort
7.8
Overall
7.9
Entertainment
7.0
Crew
8.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Comfort
7.8
Overall
7.9
Entertainment
7.0
Crew
8.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Comfort
7.8
Overall
7.9
Entertainment
7.0
Crew
8.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
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.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Warwick
Pawtucket
Peabody
Auburn
Londonderry
York Beach
Revere
Fitchburg
North Falmouth
Chelsea
Swansea
Braintree
Sandwich
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Other flights to Boston
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Portland and Boston flights
Browse other Portland and Boston flight options. Last updated on October 9, 2026.
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Top 6 airlines flying from Portland to Boston
Discover the top 6 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 7,457,451 searches. Data last updated October 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$290 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$178 | Average$355 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$208 | Average$399 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$227 | Average$364 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$236 | Average$381 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$515 | FlexibilityNo cancel fee | On-time75% |