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$171+ Cheap flights from Winnipeg (YWG) to Oregon

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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Winnipeg to Oregon

Keep the following information in mind while searching for Winnipeg to Oregon flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$325
(Kiwi.com)

One-way from

$171
(Kiwi.com)

Popular in

June

Cheapest in

July

Average price

$407
Provider with most accurate pricing for Winnipeg-Portland flight deals.
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Provider most trusted by Cheapflights users for Winnipeg-Portland flights.
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From Winnipeg to Oregon
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One-way flight from Winnipeg to Oregon
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Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Winnipeg to Oregon

Cheapest flights from Winnipeg to Oregon
Explore the most affordable flight options available from Winnipeg to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/104:55 pmYWG - PDX
1 stop19h 24mMultiple Airlines
Wed 12/172:36 pmPDX - YWG
1 stop8h 07mMultiple Airlines
Deal found 10/27$325
This Air Canada deal was found by Cheapflights users on 10/27. 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.
Thu 12/1110:45 amYWG - PDX
1 stop5h 55mAir Canada
Thu 12/183:15 pmPDX - YWG
1 stop7h 59mAir Canada
Deal found 10/27$336
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:40 amYWG - PDX
2 stops10h 53mDelta
Wed 12/177:30 pmPDX - YWG
2 stops14h 15mDelta
Deal found 10/27$340
This Air Canada deal was found by Cheapflights users on 10/27. 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.
Wed 12/249:40 pmYWG - PDX
1 stop13h 35mAir Canada
Sun 12/283:15 pmPDX - YWG
1 stop7h 59mAir Canada
Deal found 10/27$354
This Air Canada deal was found by Cheapflights users on 10/28. 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 12/186:00 amYWG - PDX
1 stop10h 40mAir Canada
Thu 1/13:15 pmPDX - YWG
1 stop7h 59mAir Canada
Deal found 10/28$374
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1112:35 pmYWG - PDX
2 stops12h 05mDelta
Wed 12/1712:32 amPDX - YWG
1 stop9h 13mDelta
Deal found 10/27$383

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Oregon 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 October 29, 2025.
Use the filters below to find and compare flights from Winnipeg to Oregon that are best for you.

Fly from

Winnipeg

Fly to

Oregon

Route

Depart

Return

Price

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 12/10

4:55 pm-10:19 am

1 stop19h 24m

Portland

Wed 12/17

2:36 pm-12:43 am

1 stop8h 07m

$325

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 3/4

10:45 am-2:40 pm

1 stop5h 55m

Portland

Thu 3/5

9:50 am-6:09 pm

1 stop6h 19m

$343

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 12/10

6:40 am-3:33 pm

2 stops10h 53m

Portland

Tue 12/16

12:32 am-11:45 am

1 stop9h 13m

$344

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 12/24

9:40 pm-9:15 am

1 stop13h 35m

Portland

Sun 12/28

3:15 pm-1:14 am

1 stop7h 59m

$354

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 12/11

8:00 am-6:30 pm

2 stops12h 30m

Portland

Thu 12/18

3:15 pm-1:14 am

1 stop7h 59m

$367

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 12/18

6:00 am-2:40 pm

1 stop10h 40m

Portland

Thu 1/1

3:15 pm-1:14 am

1 stop7h 59m

$374

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Wed 4/15

12:40 pm-11:13 pm

2 stops12h 33m

Medford

Sun 4/19

11:24 am-10:40 pm

2 stops9h 16m

$538

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Wed 4/15

8:30 am-1:09 pm

1 stop6h 39m

Medford

Sun 4/19

12:45 pm-8:48 pm

1 stop6h 03m

$586

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 12/11

12:40 pm-11:56 am

3 stops25h 16m

$171

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 12/8

6:15 am-4:37 pm

2 stops12h 22m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 13 results
1
2

Best time to book a flight from Winnipeg to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon from Winnipeg 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 Winnipeg to Oregon

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

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Oregon (average of $142). Flying from Winnipeg to Oregon in December is currently the most expensive (average of $325). 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 YWG to OR?

Find hourly flight availability from Winnipeg to Oregon. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

When flying from Winnipeg to Oregon, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 47% versus a flight at noon.

Reviews of airlines servicing Oregon

Get insights into the airlines that provide service to Oregon. 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 Oregon. Reviews last updated October 29, 2025.
Read through reviews of airlines operating flights from Winnipeg to Oregon, such as Air Canada. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,372 reviews

Boarding

7.3

Crew

7.8

Comfort

7.1

Entertainment

6.8

Overall

7.1

Food

6.3

Reviews

1 / 20
8.0
Excellent

Graeme,Sep 2025

YWG - YVR

Why not start boarding from the higher seat numbers? Easier movement for everyone. Easier to put baggage in over head lockers. Unable to get a coffee due to air turbulence, but not offered the chance to have a coffee once it had ceased.
Air Canada
7.1
Good
10,372 reviews
Air Canada
7.1
Good
10,372 reviews

Boarding

7.3

Crew

7.8

Comfort

7.1

Entertainment

6.8

Overall

7.1

Food

6.3

Reviews

1 / 20
8.0
Excellent

Graeme,Sep 2025

YWG - YVR

Why not start boarding from the higher seat numbers? Easier movement for everyone. Easier to put baggage in over head lockers. Unable to get a coffee due to air turbulence, but not offered the chance to have a coffee once it had ceased.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Oregon. 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 from for flights from Winnipeg to Oregon?

    Located just 4.6 mi from the city center, Winnipeg (YWG) is the airport most travelers will use when flying to Oregon from Winnipeg.

  • How long is the flight from Winnipeg to Oregon?

    There are many flights that can get you from Winnipeg to Oregon in 5h 55m. Fly via Air Canada, Delta, or United Airlines to get the fastest option. Airlines will cover a distance of 1208 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Oregon 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 Winnipeg to Oregon?

    Currently, August is the cheapest month in which you can book a flight from Winnipeg to Oregon (average of $142). Flying from Winnipeg to Oregon in December is currently the most expensive (average of $325). 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

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Top airline flying from Winnipeg to Oregon

Discover the top airline that operate flights from Winnipeg to Oregon. 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$214Average$330FlexibilityNo cancel feeOn-time67%

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