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Winnipeg

$159+ Cheap flights from Oregon to Winnipeg (YWG)

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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Jul 27 — Aug 31
Mon 7/27
Mon 8/3
1 adult, Economy
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Cheap flight deals from Oregon to Winnipeg

Cheapest flights from Oregon to Winnipeg
Explore the most affordable flight options available from Oregon to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 27, 2026.

This Air Canada deal was found by Cheapflights users on 6/27. 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 9/263:30 pm
PDX
-
YWG
1 stop6h 25m
Air Canada
Sat 10/35:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 6/27$350
This United deal was found by Cheapflights users on 6/27. 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 9/264:07 pm
PDX
-
YWG
2 stops18h 30m
Multiple Airlines
Sat 10/35:45 am
YWG
-
PDX
1 stop5h 46m
Multiple Airlines
Deal found 6/27$364
This Air Canada deal was found by Cheapflights users on 6/24. 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 7/237:45 pm
PDX
-
YWG
1 stop5h 17m
Air Canada
Sun 7/265:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 6/24$365
This Air Canada deal was found by Cheapflights users on 6/26. 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 8/2910:10 am
PDX
-
YWG
1 stop5h 37m
Air Canada
Mon 8/317:20 am
YWG
-
PDX
2 stops9h 31m
Air Canada
Deal found 6/26$370
This Air Canada deal was found by Cheapflights users on 6/24. 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 8/247:45 pm
PDX
-
YWG
1 stop5h 12m
Air Canada
Tue 8/257:20 am
YWG
-
PDX
2 stops9h 31m
Air Canada
Deal found 6/24$371
This Delta deal was found by Cheapflights users on 6/26. 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.
Mon 7/1312:33 am
PDX
-
YWG
1 stop9h 20m
Delta
Mon 7/203:59 pm
YWG
-
PDX
1 stop9h 19m
Delta
Deal found 6/26$380
This Air Canada deal was found by Cheapflights users on 6/22. 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 8/37:45 pm
PDX
-
YWG
1 stop5h 12m
Air Canada
Wed 8/55:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 6/22$383
This Air Canada deal was found by Cheapflights users on 6/27. 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 7/187:45 pm
PDX
-
YWG
1 stop5h 17m
Air Canada
Fri 7/319:00 pm
YWG
-
PDX
1 stop14h 31m
Air Canada
Deal found 6/27$384
This Air Canada deal was found by Cheapflights users on 6/22. 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 9/1610:10 am
PDX
-
YWG
1 stop5h 37m
Air Canada
Sat 9/265:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 6/22$387
This United deal was found by Cheapflights users on 6/26. 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.
Fri 7/3110:40 pm
PDX
-
YWG
1 stop11h 12m
Multiple Airlines
Tue 8/49:00 pm
YWG
-
PDX
1 stop14h 31m
Multiple Airlines
Deal found 6/26$388
This Air Canada deal was found by Cheapflights users on 6/27. 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 7/187:45 pm
PDX
-
YWG
1 stop5h 17m
Air Canada
Tue 7/287:20 am
YWG
-
PDX
2 stops13h 51m
Air Canada
Deal found 6/27$389
This Air Canada deal was found by Cheapflights users on 6/24. 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 8/113:30 pm
PDX
-
YWG
1 stop6h 22m
Air Canada
Sat 8/155:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 6/24$393

Find flight deals from Oregon to Winnipeg

Keep the following information in mind while searching for Oregon to Winnipeg flight deals. Data was last updated June 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$337
(Kiwi.com)

One-way from

$159
(Air Canada)

Popular in

February

Cheapest in

November

Average price

$836
Provider with most accurate pricing for Portland-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Winnipeg flights.
Search Deals
From Oregon to Winnipeg
Search Deals
One-way flight from Oregon to Winnipeg
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon 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 June 27, 2026.
Use the filters below to find and compare flights from Oregon to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 8/29

8:17 am-10:33 pm

1 stop12h 16m

Winnipeg

Mon 8/31

7:00 am-10:52 pm

1 stop17h 52m

$380

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 9/16

10:10 am-5:47 pm

1 stop5h 37m

Winnipeg

Sat 9/26

5:45 am-9:31 am

1 stop5h 46m

$387
Quickest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 8/20

7:45 pm-2:57 am

1 stop5h 12m

Winnipeg

Mon 8/24

5:45 am-9:31 am

1 stop5h 46m

$393

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 8/15

12:35 am-11:54 am

1 stop9h 19m

Winnipeg

Sun 8/23

12:46 pm-8:17 pm

1 stop9h 31m

$397

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 8/24

7:45 pm-2:57 am

1 stop5h 12m

Winnipeg

Tue 8/25

7:20 am-2:51 pm

2 stops9h 31m

$399

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 9/16

8:17 am-10:33 pm

1 stop12h 16m

Winnipeg

Sat 9/26

2:00 pm-9:27 am

2 stops21h 27m

$407

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 7/18

12:33 am-11:53 am

1 stop9h 20m

Winnipeg

Wed 7/29

3:59 pm-11:18 pm

1 stop9h 19m

$420

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 8/1

5:00 am-10:38 pm

2 stops15h 38m

Winnipeg

Mon 8/10

9:00 pm-9:31 am

1 stop14h 31m

$432
Cheapest one-way
Quickest one-way

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 8/20

7:45 pm-2:57 am

1 stop5h 12m

$159

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 7/11

4:15 pm-11:52 am

2 stops17h 37m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/24

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

Best time to book a flight from Oregon to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Oregon with our price prediction graph.
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 Oregon to Winnipeg

What is the cheapest month to book a flight from Oregon to Winnipeg?

Currently, November is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of $184). Flying from Oregon to Winnipeg in April is currently the most expensive (average of $638). 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 Oregon to Winnipeg?

Related info for your journey

Find useful and relevant information for your journey from Oregon to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Oregon?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Oregon. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • How long is the flight from Oregon to Winnipeg?

    United Airlines, Air Canada, and Delta can get you from Oregon to Winnipeg in just under 5h 37m. Your travel time can differ by up to 6h 39m. The distance between Oregon and Winnipeg is about 1208 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Oregon to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Oregon to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Winnipeg.

  • Can I find deals for business class flights from Oregon to Winnipeg?

    Yes. Cheapflights offers flight deals from Oregon to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oregon to Winnipeg?

    Currently, November is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of $184). Flying from Oregon to Winnipeg in April is currently the most expensive (average of $638). 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.

See more FAQs

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Oregon to Winnipeg

Discover the top 3 airlines that operate flights from Oregon 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 June 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$88Average$427FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$184Average$435FlexibilityNo cancel feeOn-time67%
DeltaCheapest$188Average$455FlexibilityNo cancel feeOn-timeN/A

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