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$193+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
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 February 4, 2026.

This Delta deal was found by Cheapflights users on 2/2. 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 4/2812:30 am
PDX
-
YWG
1 stop8h 26m
Delta
Sat 5/211:55 am
YWG
-
PDX
2 stops12h 26m
Delta
Deal found 2/2$457
This Air Canada deal was found by Cheapflights users on 2/2. 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 2/263:15 pm
PDX
-
YWG
1 stop7h 59m
Air Canada
Thu 3/510:40 am
YWG
-
PDX
1 stop6h 00m
Air Canada
Deal found 2/2$467
This Air Canada deal was found by Cheapflights users on 2/3. 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 7/33:25 pm
PDX
-
YWG
1 stop6h 12m
Air Canada
Sat 7/115:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 2/3$472
This Air Canada deal was found by Cheapflights users on 2/4. 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 3/183:15 pm
PDX
-
YWG
1 stop7h 59m
Air Canada
Thu 3/2610:10 pm
YWG
-
PDX
1 stop13h 05m
Air Canada
Deal found 2/4$491
This Air Canada deal was found by Cheapflights users on 2/2. 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 4/299:50 am
PDX
-
YWG
2 stops9h 30m
Air Canada
Sat 5/27:20 am
YWG
-
PDX
2 stops13h 45m
Air Canada
Deal found 2/2$503
This Air Canada deal was found by Cheapflights users on 2/1. 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 3/273:15 pm
PDX
-
YWG
1 stop7h 59m
Air Canada
Mon 3/309:15 pm
YWG
-
PDX
2 stops23h 15m
Air Canada
Deal found 2/1$528
This Delta deal was found by Cheapflights users on 2/1. 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.
Thu 3/2612:30 am
PDX
-
YWG
1 stop8h 31m
Delta
Mon 3/3011:55 am
YWG
-
PDX
1 stop10h 30m
Delta
Deal found 2/1$547

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$457
(Delta)

One-way from

$193
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$177
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. 17% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 4, 2026.
Use the filters below to find and compare flights from Oregon to Winnipeg that are best for you.

Fly from

Oregon

Fly to

Winnipeg

Route

Depart

Return

Price

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 4/28

12:30 am-10:56 am

1 stop8h 26m

Winnipeg

Sat 5/2

11:55 am-10:21 pm

2 stops12h 26m

$457

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 2/26

3:15 pm-1:14 am

1 stop7h 59m

Winnipeg

Thu 3/5

10:40 am-2:40 pm

1 stop6h 00m

$467

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 7/3

3:25 pm-11:37 pm

1 stop6h 12m

Winnipeg

Sat 7/11

5:45 am-9:31 am

1 stop5h 46m

$472

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 4/29

3:15 pm-1:14 am

1 stop7h 59m

Winnipeg

Sat 5/2

5:45 am-9:30 am

1 stop5h 45m

$473

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 3/18

3:15 pm-1:14 am

1 stop7h 59m

Winnipeg

Thu 3/26

10:10 pm-9:15 am

1 stop13h 05m

$491

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 3/30

3:15 pm-1:14 am

1 stop7h 59m

Winnipeg

Tue 3/31

10:15 pm-9:10 am

1 stop12h 55m

$492

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 3/29

3:15 pm-1:14 am

1 stop7h 59m

Winnipeg

Tue 3/31

10:15 pm-9:10 am

1 stop12h 55m

$492

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 3/5

6:00 am-7:35 pm

2 stops11h 35m

$193

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 3/5

3:15 pm-1:14 am

1 stop7h 59m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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, July is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of $139). Flying from Oregon to Winnipeg in December is currently the most expensive (average of $504). 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.

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?

    Delta and Air Canada can get you from Oregon to Winnipeg in just under 7h 59m. Your travel time can differ by up to 27m. 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, July is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of $139). Flying from Oregon to Winnipeg in December is currently the most expensive (average of $504). 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

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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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$88Average$319FlexibilityNo cancel feeOn-time60%
DeltaCheapest$143Average$424FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$164Average$320FlexibilityNo cancel feeOn-time67%

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