$273+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Dec 10 — Dec 171
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Winnipeg with Cheapflights
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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 Portland to Winnipeg
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Last-minute
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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 November 10, 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 November 10, 2026.
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/143:15 pm -
1 stop7h 17m
Wed 1/66:40 am -
1 stop5h 46m
Deal found 11/9![Air Canada logo]()
$588
This United 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/141:17 pm -
2 stops21h 06m
Wed 1/66:40 am -
1 stop5h 46m
Deal found 11/9![Multiple Airlines logo]()
$602
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Wed 12/307:25 pm -
1 stop25h 20m
Mon 1/44:00 pm -
1 stop20h 30m
Deal found 11/5![Multiple Airlines logo]()
$609
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.
Mon 12/147:25 pm -
2 stops14h 58m
Wed 1/69:40 am -
2 stops29h 37m
Deal found 11/9![United Airlines logo]()
$617
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/317:00 am -
1 stop13h 45m
Wed 1/134:45 pm -
2 stops32h 10m
Deal found 11/6![Multiple Airlines logo]()
$663
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/313:15 pm -
1 stop7h 17m
Wed 1/136:40 am -
1 stop5h 46m
Deal found 11/6![Air Canada logo]()
$674
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:28 pm -
2 stops18h 24m
Fri 1/19:40 am -
1 stop14h 36m
Deal found 11/10![United Airlines logo]()
$691
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 12/315:30 am -
2 stops13h 27m
Wed 1/138:00 am -
2 stops13h 18m
Deal found 11/6![United Airlines logo]()
$693
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 November 10, 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 November 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Wed 12/307:25 pm -
1 stop25h 20m
Mon 1/44:00 pm -
2 stops24h 42m
Deal found 11/5![Multiple Airlines logo]()
$602
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.
Mon 12/147:25 pm -
2 stops14h 58m
Wed 1/69:40 am -
2 stops29h 37m
Deal found 11/9![United Airlines logo]()
$617
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/313:15 pm -
1 stop7h 17m
Wed 1/136:40 am -
1 stop5h 46m
Deal found 11/6![Air Canada logo]()
$674
This United 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/141:17 pm -
2 stops21h 06m
Wed 1/66:40 am -
1 stop5h 46m
Deal found 11/9![Multiple Airlines logo]()
$602
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2710:00 am -
1 stop5h 57m
Tue 3/211:55 am -
1 stop5h 45m
Deal found 11/7![Air Canada logo]()
$674
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:28 pm -
2 stops18h 24m
Fri 1/19:40 am -
1 stop14h 36m
Deal found 11/10![United Airlines logo]()
$691
This United 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/3112:49 pm -
1 stop6h 08m
Wed 1/136:40 am -
1 stop5h 46m
Deal found 11/6![Multiple Airlines logo]()
$673
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/275:15 am -
2 stops11h 11m
Tue 3/28:00 am -
2 stops13h 16m
Deal found 11/7![United Airlines logo]()
$693
Last-minute flights from Portland to WinnipegDiscover last-minute flight deals from Portland to Winnipeg. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Winnipeg. Data last updated November 10, 2026 and is based on user searches.
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/143:15 pm -
1 stop7h 17m
Wed 1/66:40 am -
1 stop5h 46m
Deal found 11/9![Air Canada logo]()
$588
This United 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/141:17 pm -
2 stops21h 06m
Wed 1/66:40 am -
1 stop5h 46m
Deal found 11/9![Multiple Airlines logo]()
$602
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.
Mon 12/147:25 pm -
2 stops14h 58m
Wed 1/69:40 am -
2 stops29h 37m
Deal found 11/9![United Airlines logo]()
$617
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:28 pm -
2 stops18h 24m
Fri 1/19:40 am -
1 stop14h 36m
Deal found 11/10![United Airlines logo]()
$691
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Wed 12/307:25 pm -
1 stop25h 20m
Mon 1/44:00 pm -
1 stop20h 30m
Deal found 11/5![Multiple Airlines logo]()
$609
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/317:00 am -
1 stop13h 45m
Wed 1/134:45 pm -
2 stops32h 10m
Deal found 11/6![Multiple Airlines logo]()
$663
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/313:15 pm -
1 stop7h 17m
Wed 1/136:40 am -
1 stop5h 46m
Deal found 11/6![Air Canada logo]()
$674
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 12/315:30 am -
2 stops13h 27m
Wed 1/138:00 am -
2 stops13h 18m
Deal found 11/6![United Airlines logo]()
$693
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 November 10, 2026.
Search for one-way flight options from Portland to Winnipeg. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:51 pm -
2 stops15h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$273
This United 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 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![United Airlines logo]()
$312
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 November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $588 (Air Canada) |
One-way from | $273 (Kiwi.com) |
Popular in | February |
Cheapest in | August |
Average price | $456 |
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 November 10, 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 12/13
7:51 pm-1:10 am
3 stops26h 19m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$274
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Sun 12/13
5:00 am-9:55 pm
1 stop13h 55m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$312
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Wed 12/30
7:25 pm-11:45 pm
1 stop25h 20m
Winnipeg
Mon 1/4
4:00 pm-1:42 pm
2 stops24h 42m
$602
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Mon 12/14
1:17 pm-1:23 pm
2 stops21h 06m
Winnipeg
Wed 1/6
6:40 am-9:26 am
1 stop5h 46m
$602
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Mon 12/14
7:25 pm-1:23 pm
2 stops14h 58m
Winnipeg
Wed 1/6
9:40 am-12:17 pm
2 stops29h 37m
$617
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Thu 12/31
12:49 pm-9:57 pm
1 stop6h 08m
Winnipeg
Wed 1/13
6:40 am-9:26 am
1 stop5h 46m
$673
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Thu 12/31
3:15 pm-1:32 am
1 stop7h 17m
Winnipeg
Wed 1/13
6:40 am-9:26 am
1 stop5h 46m
$674
Quickest round-trip
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Sat 2/27
10:00 am-6:57 pm
1 stop5h 57m
Winnipeg
Tue 3/2
11:55 am-2:40 pm
1 stop5h 45m
$674
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Thu 12/24
4:28 pm-1:52 pm
2 stops18h 24m
Winnipeg
Fri 1/1
9:40 am-9:16 pm
1 stop14h 36m
$691
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Sat 2/27
5:15 am-7:26 pm
2 stops11h 11m
Winnipeg
Tue 3/2
8:00 am-6:16 pm
2 stops13h 16m
$693
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 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 |
- 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
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 November 10, 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.
Food
7.2
Boarding
8.1
Comfort
7.8
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Comfort
7.8
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Comfort
7.8
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Comfort
7.8
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
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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Find flights from Portland to Winnipeg, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Winnipeg flights
Browse other Portland and Winnipeg flight options. Last updated on November 10, 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 10, 2026.
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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 November 10, 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 November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$163 | Average$455 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$245 | Average$431 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$280 | Average$497 | FlexibilityNo cancel fee | On-time67% |