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Cheap flights from Winnipeg to Oregon from C$ 224

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
23 Apr — 30 Apr1
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 24 March 2026.

Fri 10/411:55 a.m.
YWG
-
PDX
1 stop10h 30m
Delta
Fri 17/412:30 a.m.
PDX
-
YWG
1 stop8h 26m
Delta
Deal found 21/3C$ 423
Sat 20/65:40 a.m.
YWG
-
PDX
1 stop5h 51m
Air Canada
Mon 22/67:45 p.m.
PDX
-
YWG
1 stop15h 25m
Air Canada
Deal found 22/3C$ 439
Sun 7/65:45 a.m.
YWG
-
PDX
1 stop5h 45m
Air Canada
Sun 14/63:30 p.m.
PDX
-
YWG
2 stops18h 50m
Air Canada
Deal found 19/3C$ 465
Sat 2/58:45 a.m.
YWG
-
PDX
1 stop14h 24m
United Airlines
Tue 5/51:37 p.m.
PDX
-
YWG
2 stops20h 15m
United Airlines
Deal found 23/3C$ 469
Mon 11/55:40 a.m.
YWG
-
PDX
1 stop5h 50m
Air Canada
Mon 11/57:45 p.m.
PDX
-
YWG
1 stop15h 19m
Air Canada
Deal found 22/3C$ 473
Sun 26/410:15 p.m.
YWG
-
PDX
1 stop12h 55m
Air Canada
Sun 24/53:30 p.m.
PDX
-
YWG
1 stop8h 34m
Air Canada
Deal found 19/3C$ 476
Sat 25/48:45 a.m.
YWG
-
PDX
1 stop11h 00m
United Airlines
Fri 8/57:45 p.m.
PDX
-
YWG
2 stops14h 07m
United Airlines
Deal found 21/3C$ 501
Tue 5/57:20 a.m.
YWG
-
PDX
2 stops9h 25m
Air Canada
Sat 9/57:45 p.m.
PDX
-
YWG
1 stop15h 19m
Air Canada
Deal found 22/3C$ 504
Thu 16/48:45 a.m.
YWG
-
PDX
1 stop16h 09m
United Airlines
Thu 23/44:15 p.m.
PDX
-
YWG
2 stops17h 37m
United Airlines
Deal found 19/3C$ 534
Fri 1/52:00 p.m.
YWG
-
MFR
2 stops23h 47m
United Airlines
Sat 2/52:07 p.m.
MFR
-
YWG
3 stops28h 50m
United Airlines
Deal found 19/3C$ 829
Sat 2/58:45 a.m.
YWG
-
MFR
2 stops29h 02m
United Airlines
Tue 5/52:07 p.m.
MFR
-
YWG
2 stops19h 45m
United Airlines
Deal found 23/3C$ 830

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 24 March 2026.

Round-trip from

C$ 423

One-way from

C$ 224

Popular in

February

Cheapest in

August

Average price

C$ 631
Delta
  • Delta
  • 10/4-17/4
  • 2 total stops
  • 18h 56m total
  • Winnipeg to Oregon
Search Deals
Air Canada
  • Air Canada
  • 6/6
  • 1 total stop
  • 5h 50m total
  • Winnipeg to Oregon
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 155 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 24 March 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

Sun 7/6

5:45 a.m.-9:30 a.m.

1 stop5h 45m

Portland

Sun 14/6

3:30 p.m.-12:20 p.m.

2 stops18h 50m

C$ 465

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 2/5

8:45 a.m.-9:09 p.m.

1 stop14h 24m

Portland

Tue 5/5

1:37 p.m.-11:52 a.m.

2 stops20h 15m

C$ 469
Quickest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 7/6

3:54 p.m.-11:21 p.m.

1 stop9h 27m

Portland

Sun 14/6

6:00 a.m.-4:52 p.m.

1 stop8h 52m

C$ 501

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 25/4

8:45 a.m.-12:44 a.m.

2 stops17h 59m

Portland

Fri 8/5

3:59 p.m.-11:52 a.m.

2 stops17h 53m

C$ 501

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 5/5

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

1 stop5h 50m

Portland

Sat 9/5

7:45 p.m.-1:04 p.m.

1 stop15h 19m

C$ 504

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 2/5

7:20 a.m.-2:45 p.m.

2 stops9h 25m

Portland

Tue 5/5

7:45 p.m.-12:20 p.m.

2 stops14h 35m

C$ 520

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 16/4

8:45 a.m.-10:54 p.m.

1 stop16h 09m

Portland

Thu 23/4

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

2 stops17h 37m

C$ 534

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Fri 1/5

2:00 p.m.-11:47 a.m.

2 stops23h 47m

Medford

Sat 2/5

2:07 p.m.-8:57 p.m.

3 stops28h 50m

C$ 829

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Sat 2/5

8:45 a.m.-1:01 p.m.

1 stop6h 16m

Medford

Tue 5/5

2:07 p.m.-11:52 a.m.

2 stops19h 45m

C$ 830
Cheapest one-way
Quickest one-way

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 6/6

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

1 stop5h 50m

C$ 232

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/3

Showing 1-10 of 18 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$ 188). Flying from Winnipeg to Oregon in June is currently the most expensive (average of C$ 526). 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 24 March 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
3,300 reviews
Check prices

Overall

7.2

Boarding

7.4

Crew

7.9

Comfort

7.0

Food

6.2

Entertainment

6.1

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
WestJet
7.2
Good
3,300 reviews
WestJet
7.2
Good
3,300 reviews
Check prices

Overall

7.2

Boarding

7.4

Crew

7.9

Comfort

7.0

Food

6.2

Entertainment

6.1

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
Air Canada
7.1
Good
10,836 reviews
WestJet
7.2
Good
3,300 reviews
Check prices

Overall

7.2

Boarding

7.4

Crew

7.9

Comfort

7.0

Food

6.2

Entertainment

6.1

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..

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 45m. Fly via Air Canada, United Airlines, or Delta 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$ 188). Flying from Winnipeg to Oregon in June is currently the most expensive (average of C$ 526). 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 24 March 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 223AverageC$ 324FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 291AverageC$ 465FlexibilityNo 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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