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Cheap flights from Winnipeg to Oregon from C$ 234

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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
6 Jun — 13 Jun1
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 7 May 2026.

Sun 30/810:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Wed 9/92:30 p.m.
PDX
-
YWG
1 stop7h 10m
WestJet
Deal found 3/5C$ 298
Wed 30/910:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Wed 7/102:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 6/5C$ 370
Wed 23/912:40 p.m.
YWG
-
PDX
1 stop9h 35m
Delta
Fri 25/912:40 a.m.
PDX
-
YWG
1 stop8h 54m
Delta
Deal found 3/5C$ 376
Mon 28/96:40 a.m.
YWG
-
PDX
1 stop6h 11m
Delta
Fri 2/1012:40 a.m.
PDX
-
YWG
1 stop8h 54m
Delta
Deal found 6/5C$ 389
Wed 3/67:00 a.m.
YWG
-
PDX
2 stops8h 50m
WestJet
Wed 10/62:30 p.m.
PDX
-
YWG
2 stops19h 30m
WestJet
Deal found 4/5C$ 391
Wed 23/97:00 a.m.
YWG
-
PDX
1 stop13h 47m
United Airlines
Sat 26/98:30 a.m.
PDX
-
YWG
1 stop11h 54m
United Airlines
Deal found 6/5C$ 396
Tue 2/67:00 a.m.
YWG
-
PDX
2 stops8h 50m
WestJet
Thu 4/62:30 p.m.
PDX
-
YWG
2 stops29h 10m
WestJet
Deal found 4/5C$ 400
Fri 2/1012:40 p.m.
YWG
-
MFR
2 stops12h 33m
Delta
Tue 6/105:21 p.m.
MFR
-
YWG
2 stops16h 29m
Delta
Deal found 3/5C$ 689
Fri 2/108:30 a.m.
YWG
-
MFR
1 stop14h 38m
United Airlines
Tue 6/106:34 p.m.
MFR
-
YWG
2 stops24h 14m
United Airlines
Deal found 5/5C$ 870

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 7 May 2026.

Round-trip from

C$ 298

One-way from

C$ 234

Popular in

March

Cheapest in

August

Average price

C$ 557
WestJet
  • WestJet
  • 30/8-9/9
  • 2 total stops
  • 12h 50m total
  • Winnipeg to Oregon
Search Deals
WestJet
  • WestJet
  • 6/6
  • 2 total stops
  • 8h 50m total
  • Winnipeg to Oregon
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 211 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 7 May 2026.
Use the filters below to find and compare flights from Winnipeg to Oregon that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 21/5

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

2 stops8h 50m

Portland

Fri 29/5

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

1 stop19h 45m

C$ 396

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 3/6

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

2 stops8h 50m

Portland

Wed 10/6

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

1 stop19h 45m

C$ 399

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 10/7

3:59 p.m.-11:18 p.m.

1 stop9h 19m

Portland

Sat 11/7

12:33 a.m.-11:53 a.m.

1 stop9h 20m

C$ 418

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 7/6

12:46 p.m.-8:17 p.m.

1 stop9h 31m

Portland

Sun 14/6

8:42 p.m.-11:56 a.m.

2 stops13h 14m

C$ 559

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 3/6

9:25 a.m.-1:50 p.m.

3 stops30h 25m

Portland

Wed 10/6

2:30 p.m.-12:00 p.m.

2 stops19h 30m

C$ 623
Quickest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 17/6

12:46 p.m.-8:17 p.m.

1 stop9h 31m

Portland

Sun 21/6

6:00 a.m.-4:51 p.m.

1 stop8h 51m

C$ 641

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Fri 2/10

12:40 p.m.-11:13 p.m.

2 stops12h 33m

Medford

Tue 6/10

5:21 p.m.-11:50 a.m.

2 stops16h 29m

C$ 689

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Fri 2/10

7:00 a.m.-10:59 p.m.

2 stops17h 59m

Medford

Tue 6/10

2:03 p.m.-8:48 p.m.

3 stops28h 45m

C$ 870
Cheapest one-way

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 6/6

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

2 stops8h 50m

C$ 234

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 6/6

5:40 a.m.-9:30 a.m.

1 stop5h 50m

C$ 234

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/5

Showing 1-10 of 17 resultsSorted by cheapest first
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 C$ 166). Flying from Winnipeg to Oregon in June is currently the most expensive (average of C$ 510). 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.

How much does it cost to fly round-trip from Winnipeg to Oregon?

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 7 May 2026.
Check out reviews from past customers who have flown with 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.
Air Canada
7.1
Good
11,004 reviews
Check prices

Boarding

7.3

Comfort

7.1

Entertainment

6.8

Overall

7.1

Crew

7.8

Food

6.3

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.
Air Canada
7.1
Good
11,004 reviews
Air Canada
7.1
Good
11,004 reviews
Check prices

Boarding

7.3

Comfort

7.1

Entertainment

6.8

Overall

7.1

Crew

7.8

Food

6.3

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.

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 8h 50m. Fly via WestJet, Delta, or United Airlines to get the fastest option. Winnipeg and Oregon are separated by a distance of 1944 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with 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 C$ 166). Flying from Winnipeg to Oregon in June is currently the most expensive (average of C$ 510). 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 629,999 searches. Data last updated 7 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 288AverageC$ 543FlexibilityNo 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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