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$176+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Oct 22 — Oct 291
Wed 10/22
Wed 10/29
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 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$288
(Delta)

One-way from

$176
(Kiwi.com)

Popular in

May

Cheapest in

February

Average price

$276
Provider with most accurate pricing for Portland-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Portland-Winnipeg flights.
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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. 3% potential increase in price ($11 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 22, 2025.

This Delta deal was found by Cheapflights users on 9/20. 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 10/2012:40 amPDX - YWG
1 stop8h 50mDelta
Fri 10/2412:20 pmYWG - PDX
1 stop10h 06mDelta
Deal found 9/20$288
This United Airlines deal was found by Cheapflights users on 9/20. 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 10/2011:59 pmPDX - YWG
1 stop13h 32mUnited Airlines
Wed 10/227:00 amYWG - PDX
2 stops19h 28mUnited Airlines
Deal found 9/20$293
This Delta deal was found by Cheapflights users on 9/20. 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 10/207:59 pmPDX - YWG
2 stops13h 31mDelta
Fri 10/2412:20 pmYWG - PDX
1 stop10h 06mDelta
Deal found 9/20$298
This Delta deal was found by Cheapflights users on 9/20. 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.
Wed 10/229:58 amPDX - YWG
2 stops11h 29mDelta
Fri 10/2412:20 pmYWG - PDX
2 stops12h 20mDelta
Deal found 9/20$346
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Tue 12/210:50 amPDX - YWG
1 stop11h 44mMultiple Airlines
Thu 12/44:10 pmYWG - PDX
1 stop19h 32mMultiple Airlines
Deal found 9/20$377
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Tue 10/2111:07 amPDX - YWG
2 stops10h 03mMultiple Airlines
Wed 10/229:15 pmYWG - PDX
1 stop19h 33mMultiple Airlines
Deal found 9/20$378
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 10/2211:07 amPDX - YWG
1 stop6h 16mMultiple Airlines
Thu 10/236:15 pmYWG - PDX
2 stops22h 33mMultiple Airlines
Deal found 9/20$381
This Delta deal was found by Cheapflights users on 9/20. 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 10/1912:40 amPDX - YWG
1 stop8h 50mDelta
Wed 10/228:00 amYWG - PDX
2 stops16h 40mDelta
Deal found 9/20$384
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Tue 10/2111:07 amPDX - YWG
2 stops10h 33mMultiple Airlines
Thu 10/239:15 pmYWG - PDX
1 stop19h 33mMultiple Airlines
Deal found 9/20$389

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 22, 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

Tue 10/21

12:40 am-11:30 am

1 stop8h 50m

Winnipeg

Fri 10/24

12:20 pm-8:26 pm

1 stop10h 06m

$288

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 10/22

5:00 am-1:09 pm

1 stop6h 09m

Winnipeg

Wed 10/22

4:25 pm-9:06 pm

1 stop6h 41m

$288

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 10/20

12:40 am-11:30 am

1 stop8h 50m

Winnipeg

Fri 10/24

12:20 pm-8:26 pm

1 stop10h 06m

$288

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 10/20

11:59 pm-3:31 pm

1 stop13h 32m

Winnipeg

Wed 10/22

7:00 am-12:28 am

2 stops19h 28m

$293

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 10/19

12:40 am-11:30 am

1 stop8h 50m

Winnipeg

Fri 10/24

12:20 pm-8:26 pm

1 stop10h 06m

$331

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 10/19

12:40 am-11:30 am

1 stop8h 50m

Winnipeg

Wed 10/22

8:00 am-10:40 pm

2 stops16h 40m

$384

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 10/20

11:07 am-11:10 pm

2 stops10h 03m

Winnipeg

Wed 10/22

9:15 pm-2:48 pm

1 stop19h 33m

$394

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 10/20

12:40 am-11:30 am

1 stop8h 50m

Winnipeg

Thu 10/23

9:00 am-7:06 pm

1 stop12h 06m

$412

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 11/5

7:00 am-12:39 am

2 stops15h 39m

$176

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 11/4

12:40 am-11:30 am

1 stop8h 50m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/21

Showing 1-10 of 11 results
1
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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 22, 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?

    Delta and United Airlines can get you from Oregon to Winnipeg in just under 6h 09m. Your travel time can differ by up to 2h 41m. 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, 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 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$135Average$319FlexibilityNo cancel feeOn-time60%
DeltaCheapest$143Average$484FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$183Average$336FlexibilityNo cancel feeOn-time67%

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