$138+ Cheap flights from Winnipeg (YWG) to Portland (PDX)
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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Oct 2 — Oct 91
Round-trip
1 adult, Economy
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Find cheap flights from Winnipeg to Portland 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.Cheap flight deals from Winnipeg to Portland
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Best
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Cheapest flights from Winnipeg to PortlandExplore the most affordable flight options available from Winnipeg to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 2, 2026.
Explore the most affordable flight options available from Winnipeg to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 2, 2026.
This Air Canada deal was found by Cheapflights users on 9/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:45 am -
1 stop5h 46m
Mon 9/287:45 pm -
1 stop5h 47m
Deal found 9/1![Air Canada logo]()
$248
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:45 am -
1 stop5h 46m
Thu 10/87:45 pm -
1 stop5h 12m
Deal found 8/31![Air Canada logo]()
$249
This Justfly.com deal was found by Cheapflights users on 9/1. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:15 pm -
2 stops23h 35m
Mon 9/282:30 pm -
1 stop5h 40m
Deal found 9/1![WestJet logo]()
$265
This Air Canada deal was found by Cheapflights users on 8/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:45 am -
1 stop5h 46m
Sat 9/127:45 pm -
1 stop5h 12m
Deal found 8/28![Air Canada logo]()
$282
This Delta deal was found by Cheapflights users on 9/1. 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 9/912:41 pm -
1 stop9h 35m
Fri 9/1112:25 am -
1 stop9h 26m
Deal found 9/1![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 9/1. 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.
Fri 11/65:40 pm -
1 stop8h 04m
Sun 11/812:35 am -
1 stop9h 25m
Deal found 9/1![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 8/30. 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 9/273:58 pm -
1 stop9h 12m
Sun 10/46:00 am -
1 stop8h 54m
Deal found 8/30![Delta logo]()
$302
This Air Canada deal was found by Cheapflights users on 8/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:45 am -
1 stop5h 46m
Sun 10/47:45 pm -
1 stop5h 12m
Deal found 8/30![Air Canada logo]()
$303
This WestJet deal was found by Cheapflights users on 9/1. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am -
2 stops8h 50m
Sat 9/122:30 pm -
1 stop21h 35m
Deal found 9/1![WestJet logo]()
$318
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:45 am -
1 stop5h 46m
Sun 10/253:15 pm -
1 stop7h 37m
Deal found 8/31![Air Canada logo]()
$319
This United deal was found by Cheapflights users on 8/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:45 am -
2 stops11h 46m
Sun 10/253:15 pm -
1 stop7h 37m
Deal found 8/31![Multiple Airlines logo]()
$324
Best flights from Winnipeg to PortlandDiscover carefully curated flight deals from Winnipeg to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 2, 2026.
Discover carefully curated flight deals from Winnipeg to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 2, 2026.
This Air Canada deal was found by Cheapflights users on 8/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:45 am -
1 stop5h 46m
Sat 9/127:45 pm -
1 stop5h 12m
Deal found 8/28![Air Canada logo]()
$282
This Delta deal was found by Cheapflights users on 9/1. 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 9/912:41 pm -
1 stop9h 35m
Fri 9/1112:25 am -
1 stop9h 26m
Deal found 9/1![Delta logo]()
$287
This Booking.com deal was found by Cheapflights users on 9/1. 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.
Thu 9/244:15 pm -
2 stops23h 35m
Mon 9/282:30 pm -
2 stops22h 10m
Deal found 9/1![WestJet logo]()
$287
This United Airlines deal was found by Cheapflights users on 8/28. 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.
Wed 9/97:00 am -
2 stops12h 49m
Sat 9/128:40 am -
2 stops11h 53m
Deal found 8/28![United Airlines logo]()
$287
This United deal was found by Cheapflights users on 8/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:45 am -
2 stops11h 46m
Sun 10/253:15 pm -
1 stop7h 37m
Deal found 8/31![Multiple Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 8/30. 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 9/273:58 pm -
1 stop9h 12m
Sun 10/46:00 am -
1 stop8h 54m
Deal found 8/30![Delta logo]()
$302
This WestJet deal was found by Cheapflights users on 8/31. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am -
2 stops8h 50m
Sat 9/122:30 pm -
2 stops19h 30m
Deal found 8/31![WestJet logo]()
$318
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:45 am -
1 stop5h 46m
Sun 10/253:15 pm -
1 stop7h 37m
Deal found 8/31![Air Canada logo]()
$319
This Delta deal was found by Cheapflights users on 8/30. 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 9/1312:41 pm -
1 stop9h 35m
Wed 9/236:00 am -
1 stop7h 08m
Deal found 8/30![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/31. 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 10/58:45 am -
2 stops29h 20m
Wed 10/710:43 am -
1 stop8h 14m
Deal found 8/31![United Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 8/30. 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 9/133:58 pm -
1 stop9h 12m
Sun 10/46:00 am -
1 stop8h 54m
Deal found 8/30![Delta logo]()
$349
Last-minute flights from Winnipeg to PortlandDiscover last-minute flight deals from Winnipeg to Portland. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Portland. Data last updated September 2, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 8/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:45 am -
1 stop5h 46m
Sat 9/127:45 pm -
1 stop5h 12m
Deal found 8/28![Air Canada logo]()
$282
This Delta deal was found by Cheapflights users on 9/1. 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 9/912:41 pm -
1 stop9h 35m
Fri 9/1112:25 am -
1 stop9h 26m
Deal found 9/1![Delta logo]()
$287
This WestJet deal was found by Cheapflights users on 9/1. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am -
2 stops8h 50m
Sat 9/122:30 pm -
1 stop21h 35m
Deal found 9/1![WestJet logo]()
$318
This Air Canada deal was found by Cheapflights users on 8/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:45 am -
1 stop5h 46m
Sun 10/47:45 pm -
1 stop5h 12m
Deal found 8/30![Air Canada logo]()
$303
This Air Canada deal was found by Cheapflights users on 9/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:45 am -
1 stop5h 46m
Mon 9/287:45 pm -
1 stop5h 47m
Deal found 9/1![Air Canada logo]()
$248
This Justfly.com deal was found by Cheapflights users on 9/1. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:15 pm -
2 stops23h 35m
Mon 9/282:30 pm -
1 stop5h 40m
Deal found 9/1![WestJet logo]()
$265
This Delta deal was found by Cheapflights users on 8/30. 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 9/273:58 pm -
1 stop9h 12m
Sun 10/46:00 am -
1 stop8h 54m
Deal found 8/30![Delta logo]()
$302
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:45 am -
1 stop5h 46m
Wed 10/77:45 pm -
1 stop5h 12m
Deal found 8/31![Air Canada logo]()
$249
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/910:30 pm -
2 stops41h 20m
Mon 10/122:30 pm -
1 stop19h 45m
Deal found 9/1![WestJet logo]()
$332
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:45 am -
1 stop5h 46m
Sun 10/253:15 pm -
1 stop7h 37m
Deal found 8/31![Air Canada logo]()
$319
This United deal was found by Cheapflights users on 8/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:45 am -
2 stops11h 46m
Sun 10/253:15 pm -
1 stop7h 37m
Deal found 8/31![Multiple Airlines logo]()
$324
One-way flights from Winnipeg to PortlandSearch for one-way flight options from Winnipeg to Portland. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
Search for one-way flight options from Winnipeg to Portland. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:10 am -
1 stop5h 40m
Deal found 9/2![WestJet logo]()
$138
This Air Canada deal was found by Cheapflights users on 9/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:45 am -
1 stop5h 46m
Deal found 9/2![Air Canada logo]()
$149
This deal was found by Cheapflights users on 8/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:45 am -
1 stop5h 46m
Deal found 8/31![Air Canada logo]()
$161
This United Airlines deal was found by Cheapflights users on 9/1. 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 9/242:00 pm -
2 stops22h 15m
Deal found 9/1![United Airlines logo]()
$168
This deal was found by Cheapflights users on 9/1. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:45 am -
1 stop5h 46m
Deal found 9/1![Air Canada logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:45 pm -
3 stops19h 05m
Deal found 9/2![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:15 pm -
3 stops27h 35m
Deal found 9/1![WestJet logo]()
$249
This deal was found by Cheapflights users on 8/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:45 am -
1 stop5h 46m
Deal found 8/31![Air Canada logo]()
$310
Find flight deals from Winnipeg to Portland
Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Portland (PDX). 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 September 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $248 (Air Canada) |
One-way from | $138 (Kiwi.com) |
Popular in | April |
Cheapest in | June |
Average price | $437 |
Cheapflights Fare Finder
Customize your flight search to find flights from Winnipeg to Portland 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 September 2, 2026.
Use the filters below to find and compare flights from Winnipeg to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 9/9
5:45 am-9:31 am
1 stop5h 46m
Portland
Sat 9/12
7:45 pm-2:57 am
1 stop5h 12m
$282
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 9/9
12:41 pm-8:16 pm
1 stop9h 35m
Portland
Fri 9/11
12:25 am-11:51 am
1 stop9h 26m
$287
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Thu 9/24
4:15 pm-1:50 pm
2 stops23h 35m
Portland
Mon 9/28
2:30 pm-2:40 pm
2 stops22h 10m
$287
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 9/9
7:00 am-5:49 pm
2 stops12h 49m
Portland
Sat 9/12
8:40 am-10:33 pm
2 stops11h 53m
$287
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Sun 9/27
3:58 pm-11:10 pm
1 stop9h 12m
Portland
Sun 10/4
6:00 am-4:54 pm
1 stop8h 54m
$302
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 9/9
7:00 am-1:50 pm
2 stops8h 50m
Portland
Sat 9/12
2:30 pm-12:00 pm
2 stops19h 30m
$318
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Sat 10/17
5:45 am-9:31 am
1 stop5h 46m
Portland
Sun 10/25
3:15 pm-12:52 am
1 stop7h 37m
$319
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Sat 10/17
8:45 am-6:31 pm
2 stops11h 46m
Portland
Sun 10/25
3:15 pm-12:52 am
1 stop7h 37m
$324
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Sun 9/13
12:41 pm-8:16 pm
1 stop9h 35m
Portland
Wed 9/23
6:00 am-3:08 pm
1 stop7h 08m
$339
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Sun 9/13
3:58 pm-11:10 pm
1 stop9h 12m
Portland
Sun 10/4
6:00 am-4:54 pm
1 stop8h 54m
$349
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Winnipeg to Portland
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 Winnipeg to Portland in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Winnipeg-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Portland flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Winnipeg-Portland 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 Winnipeg-Portland 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 Winnipeg to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Winnipeg with our price prediction graph.
YWG-PDX
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 Winnipeg to Portland
What is the cheapest month to book a flight from Winnipeg to Portland?
Currently, June is the cheapest month in which you can book a flight from Winnipeg to Portland (average of $330). Flying from Winnipeg to Portland in April is currently the most expensive (average of $542). 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.
How much does it cost to fly round-trip from Winnipeg to Portland?
Airfare is below average for this route at the moment.
Winnipeg to Portland flights typically cost between $275 and $469 in September.The cheapest round-trip price found within the last 5 days was $248 on Air Canada (Sep 24-Sep 28).
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated September 2, 2026.
Peruse reviews from past customers who have flown with Air Canada from Winnipeg to Portland to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.1
Entertainment
6.8
Boarding
7.3
Crew
7.8
Food
6.3
Comfort
7.1
Reviews
1 / 20
2.0
MediocreSylvia,Aug 2026
YYZ - PHL
Overall
7.1
Entertainment
6.8
Boarding
7.3
Crew
7.8
Food
6.3
Comfort
7.1
Reviews
1 / 20
2.0
MediocreSylvia,Aug 2026
YYZ - PHL
Related info for your journey
Find useful and relevant information for your journey from Winnipeg to Portland. 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 Portland?
Book flights to Portland if you plan to visit one of these locationsBeaverton
Seaside
Lincoln City
Durham
Longview
Lake Oswego
Kelso
Clackamas
Troutdale
Vancouver
Cannon Beach
McMinnville
The Dalles
Wilsonville
Stevenson
Tillamook
Hillsboro
Astoria
Gresham
Silverton
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Winnipeg to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Winnipeg and Portland flights
Browse other Winnipeg and Portland flight options. Last updated on September 2, 2026.
Other flights from Winnipeg
Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on September 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 2, 2026.
Top airline flying from Winnipeg to Portland
Discover the top airline that operate flights from Winnipeg to Portland. 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 September 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$345 | Average$441 | FlexibilityNo cancel fee | On-time67% |