$257+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Jun 13 — Jun 201
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
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 May 14, 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 May 14, 2026.
This Trip.com deal was found by Cheapflights users on 5/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:30 pm
PDX
- YWG
1 stop7h 10m
WestJet
Mon 8/2410:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 5/10![WestJet logo]()
$257
This FlightHub deal was found by Cheapflights users on 5/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/162:30 pm
PDX
- YWG
1 stop7h 10m
WestJet
Sun 8/2310:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 5/9![WestJet logo]()
$282
This Air Canada deal was found by Cheapflights users on 5/11. 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 10/193:30 pm
PDX
- YWG
1 stop6h 10m
Air Canada
Thu 10/225:45 am
YWG
- PDX
1 stop5h 46m
Air Canada
Deal found 5/11![Air Canada logo]()
$326
This FlightHub deal was found by Cheapflights users on 5/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/62:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Sat 6/137:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Deal found 5/10![WestJet logo]()
$328
This Delta deal was found by Cheapflights users on 5/11. 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 8/166:00 am
PDX
- YWG
1 stop8h 52m
Delta
Sun 8/233:58 pm
YWG
- PDX
1 stop9h 27m
Delta
Deal found 5/11![Delta logo]()
$330
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 May 14, 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 May 14, 2026.
This Delta deal was found by Cheapflights users on 5/11. 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 8/166:00 am
PDX
- YWG
1 stop8h 52m
Delta
Sun 8/233:58 pm
YWG
- PDX
1 stop9h 27m
Delta
Deal found 5/11![Delta logo]()
$330
This Air Canada deal was found by Cheapflights users on 5/13. 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 8/153:30 pm
PDX
- YWG
1 stop9h 27m
Air Canada
Wed 8/195:40 am
YWG
- PDX
1 stop5h 51m
Air Canada
Deal found 5/13![Air Canada logo]()
$334
This FlightHub deal was found by Cheapflights users on 5/12. 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.
Sun 8/162:30 pm
PDX
- YWG
2 stops22h 10m
WestJet
Sun 8/2310:30 pm
YWG
- PDX
2 stops17h 20m
WestJet
Deal found 5/12![WestJet logo]()
$335
This Mytrip deal was found by Cheapflights users on 5/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:30 pm
PDX
- YWG
1 stop5h 40m
Multiple Airlines
Sun 6/286:00 am
YWG
- PDX
3 stops18h 43m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$504
This Air Canada deal was found by Cheapflights users on 5/11. 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 10/197:45 pm
PDX
- YWG
2 stops14h 34m
Air Canada
Thu 10/227:20 am
YWG
- PDX
2 stops9h 31m
Air Canada
Deal found 5/11![Air Canada logo]()
$367
This Booking.com deal was found by Cheapflights users on 5/12. 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 6/112:30 pm
PDX
- YWG
1 stop22h 55m
WestJet
Wed 6/177:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Deal found 5/12![WestJet logo]()
$372
This Booking.com deal was found by Cheapflights users on 5/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/92:30 pm
PDX
- YWG
2 stops27h 30m
WestJet
Mon 6/154:15 pm
YWG
- PDX
2 stops23h 35m
WestJet
Deal found 5/10![WestJet logo]()
$393
Last-minute flights from Portland to WinnipegDiscover last-minute flight deals from Portland to Winnipeg. Data last updated May 14, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Winnipeg. Data last updated May 14, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 5/13. 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.
Sat 6/62:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Sat 6/137:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Deal found 5/13![WestJet logo]()
$326
This Booking.com deal was found by Cheapflights users on 5/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/92:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Mon 6/157:10 pm
YWG
- PDX
1 stop20h 40m
WestJet
Deal found 5/10![WestJet logo]()
$374
This Priceline deal was found by Cheapflights users on 5/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/112:30 pm
PDX
- YWG
1 stop8h 25m
WestJet
Wed 6/1710:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 5/12![WestJet logo]()
$359
This Air Canada deal was found by Cheapflights users on 5/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:45 pm
PDX
- YWG
1 stop15h 25m
Air Canada
Tue 6/305:30 am
YWG
- PDX
1 stop6h 01m
Air Canada
Deal found 5/9![Air Canada logo]()
$357
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 May 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (Trip.com) |
Popular in | February |
Cheapest in | November |
Average price | $427 |
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 2,558,603 searches. Data last updated May 14, 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 - YWG
PDXYWG
Portland
Sun 8/16
6:00 am-4:52 pm
1 stop8h 52m
Winnipeg
Sun 8/23
3:58 pm-11:25 pm
1 stop9h 27m
$330
Quickest round-trip
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Sat 8/15
3:30 pm-2:57 am
1 stop9h 27m
Winnipeg
Wed 8/19
5:40 am-9:31 am
1 stop5h 51m
$334
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Sun 8/16
2:30 pm-2:40 pm
2 stops22h 10m
Winnipeg
Sun 8/23
10:30 pm-1:50 pm
2 stops17h 20m
$335
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Mon 10/19
7:45 pm-12:19 pm
2 stops14h 34m
Winnipeg
Thu 10/22
7:20 am-2:51 pm
2 stops9h 31m
$367
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Thu 6/11
2:30 pm-3:25 pm
1 stop22h 55m
Winnipeg
Wed 6/17
7:00 am-1:50 pm
2 stops8h 50m
$372
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Tue 6/9
2:30 pm-8:00 pm
2 stops27h 30m
Winnipeg
Mon 6/15
4:15 pm-1:50 pm
2 stops23h 35m
$393
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Thu 6/25
2:30 pm-10:10 pm
1 stop5h 40m
Winnipeg
Sun 6/28
6:00 am-10:43 pm
3 stops18h 43m
$504
Sorted 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 May.
| 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?
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 May 14, 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.
Entertainment
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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 May 14, 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 May 14, 2026.
Popular flight searches
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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 May 14, 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 2,558,603 searches. Data last updated May 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$403 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$188 | Average$424 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$203 | Average$365 | FlexibilityNo cancel fee | On-time67% |