$146+ Cheap flights from Portland (PDX) to Winnipeg (YWG)
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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Oct 24 — Oct 311
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Winnipeg 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 Portland to Winnipeg
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to WinnipegExplore the most affordable flight options available from Portland to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2026.
Explore the most affordable flight options available from Portland to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 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.
Tue 10/203:30 pm -
1 stop6h 55m
Wed 10/215:45 am -
1 stop5h 46m
Deal found 9/19![Air Canada logo]()
$340
This United deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:30 pm -
1 stop10h 53m
Wed 11/115:40 am -
1 stop5h 46m
Deal found 9/22![Multiple Airlines logo]()
$345
This United deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/167:25 pm -
2 stops15h 27m
Thu 12/177:05 pm -
2 stops21h 36m
Deal found 9/22![Multiple Airlines logo]()
$408
This Air Canada deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:45 pm -
1 stop5h 12m
Thu 10/155:45 am -
1 stop5h 46m
Deal found 9/22![Air Canada logo]()
$446
This Air Canada deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/133:15 pm -
1 stop7h 17m
Sat 1/210:05 pm -
1 stop13h 21m
Deal found 9/22![Air Canada logo]()
$464
This Air Canada deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/143:15 pm -
2 stops7h 09m
Sun 1/39:15 pm -
1 stop14h 11m
Deal found 9/22![Air Canada logo]()
$469
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:00 am -
1 stop13h 55m
Sun 1/32:15 pm -
2 stops21h 24m
Deal found 9/22![United Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/141:17 pm -
2 stops21h 06m
Sun 1/32:15 pm -
2 stops21h 24m
Deal found 9/22![United Airlines logo]()
$475
This Air Canada deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/167:00 am -
1 stop15h 32m
Sat 1/210:05 pm -
1 stop13h 21m
Deal found 9/22![Air Canada logo]()
$483
Best flights from Portland to WinnipegDiscover carefully curated flight deals from Portland to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
Discover carefully curated flight deals from Portland to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
This Air Canada deal was found by Cheapflights users on 9/20. 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 10/87:45 pm -
1 stop5h 12m
Sun 10/115:45 am -
1 stop5h 46m
Deal found 9/20![Air Canada logo]()
$340
This United deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:30 pm -
1 stop10h 53m
Wed 11/115:40 am -
1 stop5h 46m
Deal found 9/22![Multiple Airlines logo]()
$345
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:00 am -
1 stop13h 55m
Thu 12/312:15 pm -
2 stops21h 24m
Deal found 9/22![United Airlines logo]()
$470
This Air Canada deal was found by Cheapflights users on 9/20. 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 10/203:30 pm -
1 stop6h 55m
Wed 10/215:45 am -
1 stop5h 46m
Deal found 9/20![Air Canada logo]()
$340
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.
Thu 10/227:45 pm -
1 stop5h 12m
Sat 10/245:45 am -
1 stop5h 46m
Deal found 9/19![Air Canada logo]()
$340
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/147:25 pm -
2 stops23h 30m
Fri 1/18:40 am -
1 stop16h 19m
Deal found 9/22![United Airlines logo]()
$535
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.
Thu 10/2210:28 am -
1 stop7h 32m
Fri 10/239:05 pm -
2 stops18h 48m
Deal found 9/19![Multiple Airlines logo]()
$537
Last-minute flights from Portland to WinnipegDiscover last-minute flight deals from Portland to Winnipeg. Data last updated September 24, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Winnipeg. Data last updated September 24, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:20 am -
2 stops12h 00m
Tue 9/299:05 pm -
1 stop18h 45m
Deal found 9/22![Multiple Airlines logo]()
$824
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/282:30 pm -
1 stop18h 40m
Tue 9/295:44 pm -
1 stop19h 05m
Deal found 9/22![WestJet logo]()
$874
One-way flights from Portland to WinnipegSearch for one-way flight options from Portland to Winnipeg. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
Search for one-way flight options from Portland to Winnipeg. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
This Air Canada deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:20 pm -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Air Canada logo]()
$146
This Air Canada deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:45 pm -
1 stop5h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Air Canada logo]()
$150
This Air Canada deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:05 am -
2 stops12h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Air Canada logo]()
$151
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:26 pm -
2 stops14h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![United Airlines logo]()
$156
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:00 am -
2 stops29h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![United Airlines logo]()
$161
This Air Canada deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:15 pm -
1 stop15h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Air Canada logo]()
$165
This Booking.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/142:30 pm -
1 stop5h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![WestJet logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:59 pm -
3 stops18h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:02 pm -
3 stops33h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$235
This Air Canada deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:45 pm -
1 stop5h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Air Canada logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:28 am -
3 stops10h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$238
Find flight deals from Portland to Winnipeg
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Winnipeg (YWG). 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 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $340 (Air Canada) |
One-way from | $146 (Air Canada) |
Popular in | February |
Cheapest in | November |
Average price | $428 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Winnipeg 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 24, 2026.
Use the filters below to find and compare flights from Portland to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Sun 11/1
3:20 pm-12:32 am
1 stop7h 12m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$146
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Mon 11/2
3:20 pm-12:32 am
1 stop7h 12m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$146
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Sat 10/31
3:20 pm-12:32 am
1 stop7h 12m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$146
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Wed 12/16
5:00 am-8:55 pm
1 stop13h 55m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$150
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Wed 11/4
3:15 pm-12:09 am
2 stops6h 54m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$151
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Sat 10/31
1:25 pm-1:23 pm
2 stops21h 58m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$156
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Mon 10/26
7:26 pm-12:23 pm
2 stops14h 57m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$156
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Wed 10/14
2:30 pm-10:10 pm
1 stop5h 40m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$219
Quickest round-trip
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Tue 10/13
7:45 pm-2:57 am
1 stop5h 12m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$236
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Wed 10/14
7:29 pm-12:37 pm
2 stops15h 08m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$242
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from Portland to Winnipeg
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 Winnipeg in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Winnipeg flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Winnipeg 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-Winnipeg 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 Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Portland with our price prediction graph.
PDX-YWG
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 Winnipeg
What is the cheapest month to book a flight from Portland to Winnipeg?
Currently, November is the cheapest month in which you can book a flight from Portland to Winnipeg (average of $247). Flying from Portland to Winnipeg in February is currently the most expensive (average of $878). 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 Portland to Winnipeg?
Airfare is typical for this route at the moment.
Portland to Winnipeg flights typically cost between $302 and $478 in October.The cheapest round-trip price found within the last 5 days was $340 on Air Canada (Oct 20-Oct 21).
Reviews of airlines servicing Winnipeg
Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated September 24, 2026.
Read reviews from past customers who have flown Delta,WestJet, andAir Canada from Portland to Winnipeg. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.8
Comfort
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Comfort
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Comfort
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Comfort
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Related info for your journey
Find useful and relevant information for your journey from Portland to Winnipeg. 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 Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsPortage la Prairie
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Portland and Winnipeg flights
Browse other Portland and Winnipeg flight options. Last updated on September 24, 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 September 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Winnipeg
Explore flights to Winnipeg departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 24, 2026.
Top 3 airlines flying from Portland to Winnipeg
Discover the top 3 airlines that operate flights from Portland to Winnipeg. 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 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$163 | Average$419 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$456 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$245 | Average$431 | FlexibilityNo cancel fee | On-time60% |