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$137+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$244
(Air Canada)

One-way from

$137
(Air Canada)

Popular in

June

Cheapest in

August

Average price

$269
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. 7% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Air Canada deal was found by Cheapflights users on 7/28. 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 8/215:20 amYWG - PDX
1 stop6h 10mAir Canada
Mon 8/256:15 amPDX - YWG
1 stop6h 30mAir Canada
Deal found 7/28$244
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/212:20 pmYWG - PDX
1 stop10h 05mUnited Airlines
Mon 8/251:45 pmPDX - YWG
2 stops21h 24mUnited Airlines
Deal found 7/28$303
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Fri 9/129:05 pmYWG - PDX
1 stop18h 00mWestJet
Fri 9/191:45 pmPDX - YWG
1 stop5h 45mWestJet
Deal found 7/29$314
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 8/298:30 amYWG - PDX
1 stop6h 34mDelta
Mon 9/11:45 pmPDX - YWG
1 stop7h 25mDelta
Deal found 7/29$322
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Fri 9/126:30 amYWG - PDX
2 stops10h 14mMultiple Airlines
Fri 9/191:45 pmPDX - YWG
1 stop5h 45mMultiple Airlines
Deal found 7/29$330

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 July 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

Thu 8/21

5:20 am-9:30 am

1 stop6h 10m

Portland

Mon 8/25

6:15 am-2:45 pm

1 stop6h 30m

$244

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 8/21

2:20 pm-10:25 pm

1 stop10h 05m

Portland

Mon 8/25

1:45 pm-1:09 pm

2 stops21h 24m

$303

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 9/12

9:05 pm-1:05 pm

1 stop18h 00m

Portland

Fri 9/19

1:45 pm-9:30 pm

1 stop5h 45m

$314

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 8/29

8:30 am-1:04 pm

1 stop6h 34m

Portland

Mon 9/1

1:45 pm-11:10 pm

1 stop7h 25m

$322

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 9/12

6:30 am-2:44 pm

2 stops10h 14m

Portland

Fri 9/19

1:45 pm-9:30 pm

1 stop5h 45m

$330

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 9/1

5:20 am-9:30 am

1 stop6h 10m

$137

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 9/10

4:25 pm-12:45 am

2 stops10h 20m

$150

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 9/1

6:15 pm-12:48 pm

2 stops20h 33m

$169

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Thu 9/11

6:40 am-3:34 pm

2 stops10h 54m

$277

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 8/15

9:00 am-6:57 pm

3 stops35h 57m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 11 results
1
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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, November is the cheapest month in which you can book a flight from Winnipeg to Oregon (average of $277). Flying from Winnipeg to Oregon in March is currently the most expensive (average of $368). 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 July 29, 2025.

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

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 July 29, 2025.
Read through reviews of airlines operating flights from Winnipeg to Oregon, such as Delta, United Airlines, and WestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,899 reviews
Delta
8.0
Very good
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
WestJet
7.2
Good
2,973 reviews
Delta
8.0
Very good
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air Canada
7.1
Good
9,822 reviews
Delta
8.0
Very good
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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.

  • What are the cheapest airlines to fly from Winnipeg to Oregon one-way?

    The cheapest airlines for a one-way flight from Winnipeg to Oregon are Air Canada ($137), United Airlines ($150), and WestJet ($169).

  • 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, November is the cheapest month in which you can book a flight from Winnipeg to Oregon (average of $277). Flying from Winnipeg to Oregon in March is currently the most expensive (average of $368). 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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