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$94+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Oregon to Winnipeg

Keep the following information in mind while searching for Oregon to Winnipeg flight deals. Data was last updated September 11, 2025.

Round-trip from

$237
(Air Canada)

One-way from

$94
(Mytrip)

Popular in

May

Cheapest in

February

Average price

$343
From Oregon to Winnipeg
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One-way flight from Oregon to Winnipeg
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Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Air Canada deal was found by Cheapflights users on 9/9. 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.
Wed 10/83:25 pmPDX - YWG
1 stop6h 10mAir Canada
Sun 10/126:25 pmYWG - PDX
1 stop6h 36mAir Canada
Deal found 9/9$237
This Air Canada deal was found by Cheapflights users on 9/9. 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 10/67:40 pmPDX - YWG
1 stop15h 10mAir Canada
Mon 10/135:05 amYWG - PDX
1 stop6h 15mAir Canada
Deal found 9/9$256
This United deal was found by Cheapflights users on 9/8. 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 10/83:50 pmPDX - YWG
2 stops19h 19mMultiple Airlines
Sun 10/125:05 amYWG - PDX
1 stop6h 15mMultiple Airlines
Deal found 9/8$264
This Air Canada deal was found by Cheapflights users on 9/8. 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 11/103:15 pmPDX - YWG
1 stop7h 54mAir Canada
Tue 11/1810:45 amYWG - PDX
1 stop6h 00mAir Canada
Deal found 9/8$265
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 9/181:45 pmPDX - YWG
1 stop5h 45mWestJet
Fri 9/266:30 amYWG - PDX
2 stops8h 34mWestJet
Deal found 9/8$321
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 9/181:45 pmPDX - YWG
1 stop5h 45mWestJet
Thu 9/259:05 pmYWG - PDX
1 stop17h 59mWestJet
Deal found 9/8$331
This Delta deal was found by Cheapflights users on 9/8. 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 11/117:59 pmPDX - YWG
2 stops13h 49mDelta
Tue 11/185:50 pmYWG - PDX
2 stops19h 05mDelta
Deal found 9/8$335
This Air Canada deal was found by Cheapflights users on 9/8. 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 11/103:15 pmPDX - YWG
1 stop7h 54mAir Canada
Wed 11/192:20 pmYWG - PDX
1 stop10h 15mAir Canada
Deal found 9/8$350
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 9/177:15 amPDX - YWG
2 stops31h 07mMultiple Airlines
Thu 9/259:05 pmYWG - PDX
1 stop17h 59mMultiple Airlines
Deal found 9/8$354

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 September 11, 2025.
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

Wed 10/8

3:25 pm-11:35 pm

1 stop6h 10m

Winnipeg

Sun 10/12

6:25 pm-11:01 pm

1 stop6h 36m

$237

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 10/8

3:50 pm-1:09 pm

2 stops19h 19m

Winnipeg

Sun 10/12

5:05 am-9:20 am

1 stop6h 15m

$264

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 11/10

3:15 pm-1:09 am

1 stop7h 54m

Winnipeg

Tue 11/18

10:45 am-2:45 pm

1 stop6h 00m

$265

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 11/12

3:15 pm-1:09 am

1 stop7h 54m

Winnipeg

Tue 11/18

8:00 am-6:30 pm

2 stops12h 30m

$296

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 11/11

3:15 pm-1:09 am

1 stop7h 54m

Winnipeg

Tue 11/18

8:00 am-6:30 pm

2 stops12h 30m

$296

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 11/10

3:15 pm-1:09 am

1 stop7h 54m

Winnipeg

Wed 11/19

2:20 pm-10:35 pm

1 stop10h 15m

$350

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 11/11

3:15 pm-1:09 am

1 stop7h 54m

Winnipeg

Wed 11/19

2:20 pm-10:35 pm

1 stop10h 15m

$350

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 3/3

9:50 am-6:09 pm

1 stop6h 19m

Winnipeg

Wed 3/4

10:45 am-2:45 pm

1 stop6h 00m

$363

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 11/11

12:35 am-11:48 am

1 stop9h 13m

Winnipeg

Mon 11/17

5:50 pm-8:35 am

2 stops16h 45m

$390

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 9/27

1:45 pm-11:40 pm

2 stops7h 55m

$94

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 14 results
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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, August is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of $358). Flying from Oregon to Winnipeg in December is currently the most expensive (average of $501). 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.

What is the cheapest time of day to fly from OR to YWG?

Find hourly flight availability from Oregon to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Winnipeg as you normally would.

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?

    Air Canada can get you from Oregon to Winnipeg in just under 6h 10m. Your travel time can differ by up to . The distance between Oregon and Winnipeg is about 1208 mi.

  • 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, August is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of $358). Flying from Oregon to Winnipeg in December is currently the most expensive (average of $501). 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$135Average$319FlexibilityNo cancel feeOn-time60%
DeltaCheapest$143Average$484FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$175Average$334FlexibilityNo cancel feeOn-time67%

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