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Cheap flights from Winnipeg to Oregon from C$ 251

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 24/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
28 juli — 4 aug.1
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 28 juni 2026.

fre. 11/97:00 a.m.
YWG
-
PDX
2 stops8h 50m
WestJet
søn. 13/92:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 27/6C$ 352
lør. 19/95:45 a.m.
YWG
-
PDX
1 stop5h 46m
Air Canada
man. 21/97:45 p.m.
PDX
-
YWG
1 stop5h 12m
Air Canada
Deal found 26/6C$ 417
tor. 10/95:45 a.m.
YWG
-
PDX
1 stop5h 46m
Air Canada
lør. 12/97:45 p.m.
PDX
-
YWG
1 stop5h 12m
Air Canada
Deal found 27/6C$ 419
ons. 30/97:00 a.m.
YWG
-
PDX
2 stops16h 10m
United Airlines
lør. 3/1011:30 p.m.
PDX
-
YWG
1 stop11h 07m
United Airlines
Deal found 24/6C$ 424
tor. 10/97:00 a.m.
YWG
-
PDX
2 stops19h 34m
United Airlines
lør. 12/98:40 a.m.
PDX
-
YWG
2 stops11h 53m
United Airlines
Deal found 25/6C$ 426
tor. 27/87:00 a.m.
YWG
-
PDX
1 stop17h 52m
Multiple Airlines
tir. 1/97:45 p.m.
PDX
-
YWG
1 stop5h 12m
Multiple Airlines
Deal found 26/6C$ 429
tir. 11/85:45 a.m.
YWG
-
PDX
1 stop5h 46m
Air Canada
tir. 18/87:45 p.m.
PDX
-
YWG
1 stop5h 12m
Air Canada
Deal found 24/6C$ 431
tor. 27/82:00 p.m.
YWG
-
PDX
2 stops21h 32m
United Airlines
tir. 1/910:50 a.m.
PDX
-
YWG
2 stops23h 02m
United Airlines
Deal found 26/6C$ 441
ons. 19/85:45 a.m.
YWG
-
PDX
1 stop5h 46m
Air Canada
lør. 22/87:45 p.m.
PDX
-
YWG
1 stop5h 12m
Air Canada
Deal found 23/6C$ 447
tir. 22/93:58 p.m.
YWG
-
MFR
2 stops9h 19m
Delta
lør. 26/95:29 p.m.
MFR
-
YWG
2 stops16h 27m
Delta
Deal found 24/6C$ 816
tir. 8/126:35 a.m.
YWG
-
MFR
2 stops12h 08m
Delta
ons. 9/125:21 p.m.
MFR
-
YWG
2 stops16h 29m
Delta
Deal found 25/6C$ 898
tir. 8/128:30 a.m.
YWG
-
MFR
1 stop14h 40m
United Airlines
ons. 9/125:10 a.m.
MFR
-
YWG
1 stop13h 38m
United Airlines
Deal found 25/6C$ 937

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 28 juni 2026.

Round-trip from

C$ 352

One-way from

C$ 251

Popular in

April

Cheapest in

August

Average price

C$ 532
WestJet
  • WestJet
  • 11/9-13/9
  • 3 total stops
  • 14h 30m total
  • Winnipeg to Oregon
Search Deals
Air Canada
  • Air Canada
  • 24/8
  • 1 total stop
  • 5h 46m total
  • Winnipeg to Oregon
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 148 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 28 juni 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

fre. 11/9

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

2 stops8h 50m

Portland

søn. 13/9

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

1 stop5h 40m

C$ 352

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

lør. 19/9

7:20 a.m.-2:46 p.m.

2 stops9h 26m

Portland

man. 21/9

7:45 p.m.-2:57 a.m.

1 stop5h 12m

C$ 417
Quickest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

tor. 10/9

5:45 a.m.-9:31 a.m.

1 stop5h 46m

Portland

lør. 12/9

7:45 p.m.-2:57 a.m.

1 stop5h 12m

C$ 419

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

ons. 30/9

7:00 a.m.-9:10 p.m.

2 stops16h 10m

Portland

lør. 3/10

11:30 p.m.-12:37 p.m.

1 stop11h 07m

C$ 424

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

tor. 10/9

7:00 a.m.-12:34 a.m.

2 stops19h 34m

Portland

lør. 12/9

8:40 a.m.-10:33 p.m.

2 stops11h 53m

C$ 426

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

lør. 19/9

7:00 a.m.-10:45 p.m.

2 stops17h 45m

Portland

man. 21/9

11:02 p.m.-11:52 a.m.

1 stop10h 50m

C$ 426

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

tor. 27/8

7:00 a.m.-10:52 p.m.

1 stop17h 52m

Portland

tir. 1/9

7:45 p.m.-2:57 a.m.

1 stop5h 12m

C$ 429

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

tor. 27/8

2:00 p.m.-9:32 a.m.

2 stops21h 32m

Portland

tir. 1/9

10:50 a.m.-11:52 a.m.

2 stops23h 02m

C$ 441

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

tir. 22/9

3:58 p.m.-11:17 p.m.

2 stops9h 19m

Medford

lør. 26/9

5:29 p.m.-11:56 a.m.

2 stops16h 27m

C$ 816

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

tir. 8/12

6:35 a.m.-4:43 p.m.

2 stops12h 08m

Medford

ons. 9/12

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

2 stops16h 29m

C$ 898

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/6

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$ 173). Flying from Winnipeg to Oregon in January is currently the most expensive (average of C$ 490). 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 28 juni 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
11,269 reviews
Check prices

Overall

7.1

Comfort

7.1

Boarding

7.3

Crew

7.8

Entertainment

6.8

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
11,269 reviews
Air Canada
7.1
Good
11,269 reviews
Check prices

Overall

7.1

Comfort

7.1

Boarding

7.3

Crew

7.8

Entertainment

6.8

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, Air Canada, 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$ 173). Flying from Winnipeg to Oregon in January is currently the most expensive (average of C$ 490). 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 28 juni 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 370AverageC$ 604FlexibilityNo 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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