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Cheap flights from Winnipeg to Oregon from C$ 214

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 31/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
6 Mar — 13 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Oregon

Enter your travel dates to find the best prices.

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 4 February 2026.

Mon 18/510:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Sat 23/52:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 2/2C$ 412
Tue 19/510:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Sun 24/52:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 3/2C$ 415
Mon 1/612:10 p.m.
YWG
-
PDX
1 stop27h 40m
WestJet
Sat 6/62:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 2/2C$ 434
Mon 18/57:00 a.m.
YWG
-
PDX
2 stops8h 50m
WestJet
Sun 24/52:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 3/2C$ 448
Mon 25/55:30 p.m.
YWG
-
PDX
2 stops22h 20m
WestJet
Sat 30/52:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 2/2C$ 500
Tue 3/22:20 p.m.
YWG
-
MFR
2 stops23h 54m
United Airlines
Fri 6/26:00 a.m.
MFR
-
YWG
2 stops27h 57m
United Airlines
Deal found 2/2C$ 1,206

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 4 February 2026.

Round-trip from

C$ 412

One-way from

C$ 214

Popular in

January

Cheapest in

August

Average price

C$ 418
WestJet
  • WestJet
  • 18/5-23/5
  • 2 total stops
  • 11h 20m total
  • Winnipeg to Oregon
Search Deals
WestJet
  • WestJet
  • 31/5
  • 1 total stop
  • 5h 40m total
  • Winnipeg to Oregon
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 110 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 46 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 629,999 searches. Data last updated 4 February 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 18/5

10:10 a.m.-1:50 p.m.

1 stop5h 40m

Portland

Sun 24/5

2:30 p.m.-10:10 p.m.

1 stop5h 40m

C$ 414

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 19/5

10:10 a.m.-1:50 p.m.

1 stop5h 40m

Portland

Sun 24/5

2:30 p.m.-10:10 p.m.

1 stop5h 40m

C$ 415

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 18/5

7:00 a.m.-1:50 p.m.

2 stops8h 50m

Portland

Sat 23/5

2:30 p.m.-12:15 p.m.

1 stop19h 45m

C$ 463

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 25/5

6:00 a.m.-1:50 p.m.

1 stop9h 50m

Portland

Sat 30/5

2:30 p.m.-12:55 a.m.

1 stop8h 25m

C$ 504

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 21/4

10:45 a.m.-2:40 p.m.

1 stop5h 55m

Portland

Sun 26/4

3:15 p.m.-1:14 a.m.

1 stop7h 59m

C$ 533

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 21/4

6:15 a.m.-8:32 p.m.

2 stops16h 17m

Portland

Sun 26/4

2:30 p.m.-12:55 a.m.

1 stop8h 25m

C$ 534

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 20/4

5:25 p.m.-1:46 p.m.

1 stop22h 21m

Portland

Sat 25/4

10:31 a.m.-4:40 p.m.

1 stop28h 09m

C$ 535

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 20/4

2:00 p.m.-9:48 a.m.

2 stops21h 48m

Portland

Thu 23/4

4:15 p.m.-11:52 a.m.

2 stops17h 37m

C$ 540

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 20/4

2:00 p.m.-9:48 a.m.

2 stops21h 48m

Portland

Sat 25/4

7:14 p.m.-11:52 a.m.

2 stops14h 38m

C$ 540

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 7/4

2:00 p.m.-9:48 a.m.

2 stops21h 48m

Portland

Tue 14/4

1:39 p.m.-11:52 a.m.

2 stops20h 13m

C$ 540

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

Showing 1-10 of 22 results
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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, August is the cheapest month in which you can book a flight from Winnipeg to Oregon (average of C$ 191). Flying from Winnipeg to Oregon in January is currently the most expensive (average of C$ 482). 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 4 February 2026.
Check out reviews from past customers who have flown with WestJet and Air Canada from Winnipeg to Oregon to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,255 reviews
Check prices

Crew

7.9

Overall

7.2

Comfort

7.0

Entertainment

6.1

Boarding

7.4

Food

6.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying
WestJet
7.2
Good
3,255 reviews
WestJet
7.2
Good
3,255 reviews
Check prices

Crew

7.9

Overall

7.2

Comfort

7.0

Entertainment

6.1

Boarding

7.4

Food

6.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying
Air Canada
7.1
Good
10,688 reviews
WestJet
7.2
Good
3,255 reviews
Check prices

Crew

7.9

Overall

7.2

Comfort

7.0

Entertainment

6.1

Boarding

7.4

Food

6.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying

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 7.3 km from the city centre, Winnipeg (YWG) is the airport most travellers 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. Winnipeg and Oregon are separated by a distance of 1944 km.

  • 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 C$ 191). Flying from Winnipeg to Oregon in January is currently the most expensive (average of C$ 482). 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 2 airlines flying from Winnipeg to Oregon

Discover the top 2 airlines 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 629,999 searches. Data last updated 4 February 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 226AverageC$ 433FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 308AverageC$ 431FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Oregon?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to Oregon. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Oregon?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Oregon from Winnipeg.

Can Cheapflights find flights from Winnipeg to Oregon with no change fees?

Certainly. Search results for flights to Oregon from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Winnipeg to Oregon become cheaper?

Yes! Start tracking prices for Winnipeg to Oregon flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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