$209+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Dec 11 — Dec 181
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 82 days in advance, depart on a Thursday or Wednesday 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 November 11, 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 November 11, 2026.
This Alaska Airlines deal was found by Cheapflights users on 11/7. 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.
Tue 12/17:59 pm -
1 stop18h 10m
Tue 12/86:13 pm -
1 stop25h 37m
Deal found 11/7![Alaska Airlines logo]()
$345
This Alaska Airlines deal was found by Cheapflights users on 11/9. 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.
Wed 12/27:59 pm -
1 stop18h 09m
Tue 12/86:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$351
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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.
Tue 12/87:59 pm -
1 stop18h 10m
Tue 12/156:13 pm -
1 stop18h 37m
Deal found 11/10![Alaska Airlines logo]()
$355
This Alaska Airlines deal was found by Cheapflights users on 11/9. 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.
Wed 12/27:59 pm -
1 stop18h 09m
Mon 12/76:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Mon 12/77:59 pm -
1 stop18h 10m
Tue 12/156:13 pm -
1 stop18h 37m
Deal found 11/8![Alaska Airlines logo]()
$360
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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.
Tue 12/87:59 pm -
1 stop18h 10m
Mon 12/146:13 pm -
1 stop18h 37m
Deal found 11/10![Alaska Airlines logo]()
$361
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Mon 12/77:59 pm -
1 stop18h 10m
Mon 12/146:13 pm -
1 stop18h 37m
Deal found 11/8![Alaska Airlines logo]()
$366
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Fri 12/47:59 pm -
1 stop18h 09m
Tue 12/86:13 pm -
1 stop29h 37m
Deal found 11/8![Alaska Airlines logo]()
$370
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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.
Tue 12/82:51 pm -
1 stop23h 18m
Fri 12/116:13 pm -
1 stop25h 37m
Deal found 11/10![Alaska Airlines logo]()
$371
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Mon 12/77:00 am -
1 stop31h 09m
Wed 12/166:13 pm -
1 stop27h 59m
Deal found 11/8![Alaska Airlines logo]()
$375
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Fri 12/47:59 pm -
1 stop18h 09m
Mon 12/146:13 pm -
1 stop18h 37m
Deal found 11/8![Alaska Airlines logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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.
Wed 12/27:59 pm -
1 stop18h 09m
Fri 12/116:13 pm -
1 stop22h 25m
Deal found 11/10![Alaska Airlines logo]()
$377
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 November 11, 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 November 11, 2026.
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Thu 2/252:31 pm -
1 stop22h 02m
Mon 3/14:36 pm -
1 stop29h 51m
Deal found 11/8![Alaska Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 11/6. 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.
Mon 3/16:10 am -
1 stop7h 05m
Wed 3/34:30 pm -
1 stop8h 50m
Deal found 11/6![Southwest logo]()
$446
This Delta deal was found by Cheapflights users on 11/9. 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 2/41:43 pm -
1 stop7h 06m
Mon 2/86:00 pm -
1 stop8h 58m
Deal found 11/9![Delta logo]()
$447
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Mon 1/47:12 pm -
1 stop7h 42m
Sat 1/99:09 am -
2 stops11h 50m
Deal found 11/6![United Airlines logo]()
$451
This Delta deal was found by Cheapflights users on 11/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/255:45 pm -
1 stop9h 48m
Mon 3/297:05 am -
1 stop9h 13m
Deal found 11/8![Delta logo]()
$447
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Thu 12/3111:42 pm -
2 stops9h 28m
Mon 1/42:32 pm -
1 stop9h 05m
Deal found 11/6![United Airlines logo]()
$452
This Southwest deal was found by Cheapflights users on 11/6. 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.
Sat 12/58:30 am -
2 stops10h 30m
Sat 12/125:35 am -
2 stops11h 45m
Deal found 11/6![Southwest logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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.
Sun 12/209:22 pm -
1 stop29h 06m
Sun 1/36:00 am -
Nonstop6h 40m
Deal found 11/10![Alaska Airlines logo]()
$471
This Southwest deal was found by Cheapflights users on 11/8. 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 12/1410:15 am -
2 stops10h 30m
Fri 1/15:00 am -
1 stop8h 40m
Deal found 11/8![Southwest logo]()
$476
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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.
Tue 12/87:29 am -
Nonstop5h 24m
Tue 12/154:56 pm -
Nonstop6h 33m
Deal found 11/10![Alaska Airlines logo]()
$497
This Southwest deal was found by Cheapflights users on 11/9. 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 12/26:55 am -
2 stops12h 00m
Sun 12/63:30 pm -
2 stops10h 15m
Deal found 11/9![Southwest logo]()
$492
This Southwest deal was found by Cheapflights users on 11/6. 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 12/410:10 am -
2 stops9h 05m
Fri 12/115:35 am -
2 stops11h 15m
Deal found 11/6![Southwest logo]()
$516
Last-minute flights from Portland to BostonDiscover last-minute flight deals from Portland to Boston. Data last updated November 11, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Boston. Data last updated November 11, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 11/7. 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.
Tue 12/17:59 pm -
1 stop18h 10m
Tue 12/86:13 pm -
1 stop25h 37m
Deal found 11/7![Alaska Airlines logo]()
$345
This Alaska Airlines deal was found by Cheapflights users on 11/9. 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.
Wed 12/27:59 pm -
1 stop18h 09m
Tue 12/86:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$351
This Alaska Airlines deal was found by Cheapflights users on 11/9. 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.
Wed 12/27:59 pm -
1 stop18h 09m
Mon 12/76:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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.
Wed 12/27:59 pm -
1 stop18h 09m
Fri 12/116:13 pm -
1 stop22h 25m
Deal found 11/10![Alaska Airlines logo]()
$377
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Fri 12/47:59 pm -
1 stop18h 09m
Tue 12/86:13 pm -
1 stop29h 37m
Deal found 11/8![Alaska Airlines logo]()
$370
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Fri 12/47:59 pm -
1 stop18h 09m
Mon 12/76:13 pm -
1 stop27h 45m
Deal found 11/8![Alaska Airlines logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Mon 12/77:59 pm -
1 stop18h 10m
Tue 12/156:13 pm -
1 stop18h 37m
Deal found 11/8![Alaska Airlines logo]()
$360
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Mon 12/77:59 pm -
1 stop18h 10m
Mon 12/146:13 pm -
1 stop18h 37m
Deal found 11/8![Alaska Airlines logo]()
$366
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Mon 12/77:00 am -
1 stop31h 09m
Wed 12/166:13 pm -
1 stop27h 59m
Deal found 11/8![Alaska Airlines logo]()
$375
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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.
Tue 12/87:59 pm -
1 stop18h 10m
Tue 12/156:13 pm -
1 stop18h 37m
Deal found 11/10![Alaska Airlines logo]()
$355
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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.
Tue 12/87:59 pm -
1 stop18h 10m
Mon 12/146:13 pm -
1 stop18h 37m
Deal found 11/10![Alaska Airlines logo]()
$361
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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.
Tue 12/82:51 pm -
1 stop23h 18m
Fri 12/116:13 pm -
1 stop25h 37m
Deal found 11/10![Alaska Airlines logo]()
$371
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 November 11, 2026.
Search for one-way flight options from Portland to Boston. Find affordable one-way fares based on user searches. Data last updated November 11, 2026.
This Alaska Airlines deal was found by Cheapflights users on 11/9. 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 1/218:08 pm -
1 stop16h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Alaska Airlines logo]()
$209
This Booking.com deal was found by Cheapflights users on 11/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/162:41 pm -
2 stops11h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Alaska Airlines logo]()
$211
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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.
Wed 12/910:30 am -
1 stop27h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Alaska Airlines logo]()
$218
This Expedia deal was found by Cheapflights users on 11/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/212:52 pm -
1 stop11h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Alaska Airlines logo]()
$219
This Mytrip deal was found by Cheapflights users on 11/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/239:22 pm -
1 stop16h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Alaska Airlines logo]()
$222
This United Airlines deal was found by Cheapflights users on 11/9. 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 12/2311:50 pm -
1 stop7h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![United Airlines logo]()
$223
This Delta deal was found by Cheapflights users on 11/9. 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 12/611:10 pm -
1 stop10h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$224
This Southwest deal was found by Cheapflights users on 11/9. 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 12/810:15 am -
2 stops10h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Southwest logo]()
$228
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Thu 12/1711:50 pm -
2 stops9h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![United Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 11/6. 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.
Mon 2/155:50 am -
2 stops12h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Southwest logo]()
$243
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 November 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $345 (Alaska Airlines) |
One-way from | $209 (Alaska Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $535 |
Good round-trip deal | $497 or less |
Good one-way deal | $243 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 November 11, 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
Thu 1/21
10:33 am-3:52 pm
1 stop26h 19m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$219
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sun 5/2
4:15 pm-6:40 am
1 stop11h 25m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$224
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Mon 1/4
11:59 pm-10:42 am
1 stop7h 43m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$224
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Thu 12/17
5:59 pm-7:19 am
1 stop10h 20m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$224
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Thu 12/24
11:55 am-11:38 pm
1 stop8h 43m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$224
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Wed 12/2
5:00 am-5:55 pm
2 stops9h 55m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$228
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Mon 3/1
5:15 am-7:05 pm
2 stops10h 50m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$229
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sun 1/3
9:50 pm-6:20 am
Nonstop5h 30m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$249
Quickest round-trip
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sun 12/6
7:29 am-3:53 pm
Nonstop5h 24m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$249
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Thu 12/31
7:15 am-3:43 pm
Nonstop5h 28m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$249
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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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
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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 $327). Flying from Portland to Boston in December is currently the most expensive (average of $541). 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 November 11, 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 33% 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 November 11, 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.
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.0
Overall
7.9
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
Revere
Fitchburg
Londonderry
York Beach
North Falmouth
Chelsea
Swansea
Braintree
Auburn
Sandwich
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Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 11, 2026.
Complete your trip
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Portland and Boston flights
Browse other Portland and Boston flight options. Last updated on November 11, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on November 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 November 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$109 | Average$304 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$179 | Average$366 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$227 | Average$365 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$236 | Average$409 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$236 | Average$377 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$287 | Average$521 | FlexibilityNo cancel fee | On-time75% |