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$157+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap 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 February 4, 2026.

This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1810:10 am
YWG
-
PDX
1 stop5h 40m
WestJet
Sat 5/232:30 pm
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 2/2$302
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1910:10 am
YWG
-
PDX
1 stop5h 40m
WestJet
Sun 5/242:30 pm
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 2/3$304
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:10 pm
YWG
-
PDX
1 stop27h 40m
WestJet
Sat 6/62:30 pm
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 2/2$318
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:00 am
YWG
-
PDX
2 stops8h 50m
WestJet
Sun 5/242:30 pm
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 2/3$328
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:30 pm
YWG
-
PDX
2 stops22h 20m
WestJet
Sat 5/302:30 pm
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 2/2$366
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/32:20 pm
YWG
-
MFR
2 stops23h 54m
United Airlines
Fri 2/66:00 am
MFR
-
YWG
2 stops27h 57m
United Airlines
Deal found 2/2$883

Find flight deals from Winnipeg to Oregon

Keep the following information in mind while searching for Winnipeg to Oregon flight deals. Data was last updated February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$302
(Trip.com)

One-way from

$157
(oojo)

Popular in

January

Cheapest in

August

Average price

$306
Provider with most accurate pricing for Winnipeg-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Portland flights.
Search Deals
From Winnipeg to Oregon
Search Deals
One-way flight from Winnipeg to Oregon
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% 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 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 February 4, 2026.
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

Mon 5/18

10:10 am-1:50 pm

1 stop5h 40m

Portland

Sun 5/24

2:30 pm-10:10 pm

1 stop5h 40m

$303

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 5/19

10:10 am-1:50 pm

1 stop5h 40m

Portland

Sun 5/24

2:30 pm-10:10 pm

1 stop5h 40m

$304

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 6/1

12:10 pm-1:50 pm

1 stop27h 40m

Portland

Sat 6/6

2:30 pm-10:10 pm

1 stop5h 40m

$318

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 5/18

7:00 am-1:50 pm

2 stops8h 50m

Portland

Sat 5/23

2:30 pm-12:15 pm

1 stop19h 45m

$339

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 5/25

6:00 am-1:50 pm

1 stop9h 50m

Portland

Sat 5/30

2:30 pm-12:55 am

1 stop8h 25m

$369

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 4/20

5:25 pm-1:46 pm

1 stop22h 21m

Portland

Sat 4/25

6:00 am-4:40 pm

2 stops8h 40m

$375

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 4/21

10:45 am-2:40 pm

1 stop5h 55m

Portland

Sun 4/26

3:15 pm-1:14 am

1 stop7h 59m

$390

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 4/21

6:15 am-8:32 pm

2 stops16h 17m

Portland

Sun 4/26

2:30 pm-12:55 am

1 stop8h 25m

$391

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 5/31

10:10 am-1:50 pm

1 stop5h 40m

$157

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 5/29

9:05 pm-1:50 pm

1 stop18h 45m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 20 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 $140). Flying from Winnipeg to Oregon in January is currently the most expensive (average of $353). 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.

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 February 4, 2026.
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
10,688 reviews

Comfort

7.1

Crew

7.8

Overall

7.1

Food

6.3

Entertainment

6.8

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍
Air Canada
7.1
Good
10,688 reviews
Air Canada
7.1
Good
10,688 reviews

Comfort

7.1

Crew

7.8

Overall

7.1

Food

6.3

Entertainment

6.8

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍

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 40m. Fly via WestJet to get the fastest option. Airlines will cover a distance of 1208 mi.

  • 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 $140). Flying from Winnipeg to Oregon in January is currently the most expensive (average of $353). 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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$214Average$345FlexibilityNo cancel feeOn-time67%

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