$163+ Cheap flights from Winnipeg (YWG) to Portland (PDX)
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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Oct 20 — Oct 271
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
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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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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 20, 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 20, 2026.
This Ticket deal was found by Cheapflights users on 9/17. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:45 am -
1 stop5h 46m
Wed 10/73:30 pm -
1 stop6h 55m
Deal found 9/17![Air Canada logo]()
$264
This Air Canada deal was found by Cheapflights users on 9/15. 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 10/37:20 am -
2 stops9h 26m
Mon 10/57:45 pm -
1 stop5h 12m
Deal found 9/15![Air Canada logo]()
$278
This Air Canada deal was found by Cheapflights users on 9/16. 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 10/315:40 am -
1 stop5h 46m
Sat 11/73:15 pm -
1 stop7h 17m
Deal found 9/16![Air Canada logo]()
$280
This United Airlines deal was found by Cheapflights users on 9/19. 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 10/62:00 pm -
1 stop10h 23m
Wed 10/74:09 pm -
2 stops18h 28m
Deal found 9/19![United Airlines logo]()
$296
This Mytrip deal was found by Cheapflights users on 9/17. 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.
Thu 10/19:05 pm -
3 stops24h 06m
Wed 10/77:45 pm -
1 stop5h 12m
Deal found 9/17![Multiple Airlines logo]()
$373
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 20, 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 20, 2026.
This Air Canada deal was found by Cheapflights users on 9/15. 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 10/35:45 am -
1 stop5h 46m
Mon 10/57:45 pm -
1 stop5h 12m
Deal found 9/15![Air Canada logo]()
$278
This United Airlines deal was found by Cheapflights users on 9/19. 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 10/68:45 am -
2 stops16h 12m
Wed 10/74:09 pm -
2 stops18h 28m
Deal found 9/19![United Airlines logo]()
$296
This Air Canada deal was found by Cheapflights users on 9/16. 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 10/315:40 am -
1 stop5h 46m
Sat 11/73:15 pm -
1 stop7h 17m
Deal found 9/16![Air Canada logo]()
$280
This Air Canada deal was found by Cheapflights users on 9/19. 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.
Tue 10/65:45 am -
1 stop5h 46m
Wed 10/77:45 pm -
1 stop5h 12m
Deal found 9/19![Air Canada logo]()
$290
This Ticket deal was found by Cheapflights users on 9/17. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:45 am -
1 stop5h 46m
Wed 10/77:45 pm -
2 stops14h 34m
Deal found 9/17![Air Canada logo]()
$294
Last-minute flights from Winnipeg to PortlandDiscover last-minute flight deals from Winnipeg to Portland. Data last updated September 20, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Portland. Data last updated September 20, 2026 and is based on user searches.
This Ticket deal was found by Cheapflights users on 9/17. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:45 am -
1 stop5h 46m
Wed 10/73:30 pm -
1 stop6h 55m
Deal found 9/17![Air Canada logo]()
$264
This Mytrip deal was found by Cheapflights users on 9/17. 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.
Thu 10/19:05 pm -
3 stops24h 06m
Wed 10/77:45 pm -
1 stop5h 12m
Deal found 9/17![Multiple Airlines logo]()
$373
This Air Canada deal was found by Cheapflights users on 9/15. 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 10/37:20 am -
2 stops9h 26m
Mon 10/57:45 pm -
1 stop5h 12m
Deal found 9/15![Air Canada logo]()
$278
This United Airlines deal was found by Cheapflights users on 9/19. 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 10/62:00 pm -
1 stop10h 23m
Wed 10/74:09 pm -
2 stops18h 28m
Deal found 9/19![United Airlines logo]()
$296
This Air Canada deal was found by Cheapflights users on 9/16. 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 10/315:40 am -
1 stop5h 46m
Sat 11/73:15 pm -
1 stop7h 17m
Deal found 9/16![Air Canada logo]()
$280
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 20, 2026.
Search for one-way flight options from Winnipeg to Portland. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
This Air Canada deal was found by Cheapflights users on 9/19. 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.
Sun 10/255:00 am -
1 stop6h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Air Canada logo]()
$163
This Air Canada deal was found by Cheapflights users on 9/16. 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 11/255:40 am -
1 stop5h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Air Canada logo]()
$165
This Air Canada deal was found by Cheapflights users on 9/17. 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 11/25:40 am -
1 stop5h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Air Canada logo]()
$170
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:40 pm -
1 stop8h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Delta logo]()
$175
This United Airlines deal was found by Cheapflights users on 9/19. 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 10/292:15 pm -
2 stops21h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![United Airlines logo]()
$181
This United Airlines deal was found by Cheapflights users on 9/16. 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 11/252:15 pm -
2 stops21h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$182
This Air Canada deal was found by Cheapflights users on 9/19. 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.
Tue 10/277:05 pm -
2 stops16h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Air Canada logo]()
$187
This Air Canada deal was found by Cheapflights users on 9/16. 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 11/267:05 pm -
2 stops16h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Air Canada logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Mon 11/22:10 pm -
2 stops23h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Fri 10/307:00 am -
3 stops28h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$269
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 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $264 (Ticket) |
One-way from | $163 (Air Canada) |
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 20, 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 10/28
5:40 am-9:26 am
1 stop5h 46m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$163
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Mon 11/2
5:40 am-9:26 am
1 stop5h 46m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$170
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Fri 10/30
2:15 pm-11:09 pm
2 stops10h 54m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$175
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Tue 10/27
5:40 pm-11:44 pm
1 stop8h 04m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$175
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Thu 10/29
2:15 pm-9:36 am
2 stops21h 21m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$181
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 11/25
2:15 pm-9:36 am
2 stops21h 21m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$182
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Fri 11/27
7:05 pm-9:26 am
2 stops16h 21m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$200
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Thu 11/26
7:05 pm-9:26 am
2 stops16h 21m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$200
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Mon 11/2
5:00 am-8:47 pm
3 stops17h 47m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$271
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Sat 10/3
5:45 am-9:31 am
1 stop5h 46m
Portland
Mon 10/5
7:45 pm-2:57 am
1 stop5h 12m
$278
Showing 1-10 of 17 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 $347 and $462 in October.The cheapest round-trip price found within the last 5 days was $264 on Air Canada (Oct 1-Oct 7).
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 20, 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.
Entertainment
6.8
Overall
7.1
Comfort
7.1
Food
6.3
Crew
7.8
Boarding
7.3
Reviews
1 / 20
2.0
MediocreSylvia,Aug 2026
YYZ - PHL
Entertainment
6.8
Overall
7.1
Comfort
7.1
Food
6.3
Crew
7.8
Boarding
7.3
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
Cannon Beach
Vancouver
Kelso
Troutdale
Clackamas
McMinnville
The Dalles
Wilsonville
Stevenson
Tillamook
Hillsboro
Astoria
Gresham
Silverton
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Winnipeg and Portland flights
Browse other Winnipeg and Portland flight options. Last updated on September 20, 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 20, 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 20, 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 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$345 | Average$503 | FlexibilityNo cancel fee | On-time67% |