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Cheap flights from Winnipeg to Oregon from C$ 163

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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
14 Oct — 21 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Winnipeg to Oregon

Keep the following information in mind while searching for Winnipeg to Oregon flight deals. Data was last updated 14 September 2025.

Round-trip from

C$ 327

One-way from

C$ 163

Popular in

June

Cheapest in

July

Average price

C$ 505
Air Canada
  • Air Canada
  • 7/10-14/10
  • 2 total stops
  • 19h 58m total
  • Winnipeg to Oregon
Search Deals
Air Canada
  • Air Canada
  • 4/10
  • 1 total stop
  • 6h 15m total
  • Winnipeg to Oregon
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find 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 14 September 2025.

Tue 7/107:10 p.m.YWG - PDX
1 stop5h 51mAir Canada
Tue 14/109:55 a.m.PDX - YWG
1 stop14h 07mAir Canada
Deal found 13/9C$ 327
Tue 7/1012:20 p.m.YWG - PDX
1 stop10h 06mDelta
Tue 14/107:59 p.m.PDX - YWG
2 stops13h 31mDelta
Deal found 13/9C$ 334
Fri 24/107:10 p.m.YWG - PDX
1 stop5h 51mAir Canada
Mon 27/103:15 p.m.PDX - YWG
1 stop7h 54mAir Canada
Deal found 14/9C$ 336
Fri 24/104:25 p.m.YWG - PDX
2 stops10h 03mMultiple Airlines
Mon 27/103:15 p.m.PDX - YWG
1 stop7h 54mMultiple Airlines
Deal found 14/9C$ 401
Thu 18/1210:45 a.m.YWG - PDX
1 stop6h 00mAir Canada
Thu 1/13:15 p.m.PDX - YWG
1 stop7h 54mAir Canada
Deal found 12/9C$ 412
Wed 26/112:20 p.m.YWG - PDX
2 stops21h 18mMultiple Airlines
Sun 30/113:15 p.m.PDX - YWG
1 stop7h 54mMultiple Airlines
Deal found 12/9C$ 480
Sun 21/122:20 p.m.YWG - PDX
2 stops21h 41mUnited Airlines
Mon 29/1211:55 p.m.PDX - YWG
1 stop10h 02mUnited Airlines
Deal found 14/9C$ 489
Wed 26/117:30 a.m.YWG - PDX
1 stop14h 00mDelta
Sat 29/1112:35 a.m.PDX - YWG
1 stop9h 13mDelta
Deal found 12/9C$ 512

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 14 September 2025.
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

Tue 7/10

12:20 p.m.-8:26 p.m.

1 stop10h 06m

Portland

Tue 14/10

7:59 p.m.-11:30 a.m.

2 stops13h 31m

C$ 334

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 24/10

7:10 p.m.-11:01 p.m.

1 stop5h 51m

Portland

Mon 27/10

3:15 p.m.-1:09 a.m.

1 stop7h 54m

C$ 336

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 24/10

4:25 p.m.-12:28 a.m.

2 stops10h 03m

Portland

Mon 27/10

3:15 p.m.-1:09 a.m.

1 stop7h 54m

C$ 401

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 18/12

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

1 stop6h 00m

Portland

Thu 1/1

3:15 p.m.-1:09 a.m.

1 stop7h 54m

C$ 412

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 4/3

8:00 a.m.-2:45 p.m.

2 stops8h 45m

Portland

Thu 5/3

3:15 p.m.-1:09 a.m.

1 stop7h 54m

C$ 430

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 4/3

2:20 p.m.-9:40 a.m.

2 stops21h 20m

Portland

Thu 5/3

3:41 p.m.-11:39 a.m.

2 stops17h 58m

C$ 439

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 26/11

2:20 p.m.-9:38 a.m.

2 stops21h 18m

Portland

Sun 30/11

3:15 p.m.-1:09 a.m.

1 stop7h 54m

C$ 480

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 21/12

2:20 p.m.-10:01 a.m.

2 stops21h 41m

Portland

Mon 29/12

11:55 p.m.-11:57 a.m.

1 stop10h 02m

C$ 489

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 26/11

7:30 a.m.-7:30 p.m.

1 stop14h 00m

Portland

Sat 29/11

12:35 a.m.-11:48 a.m.

1 stop9h 13m

C$ 512

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 4/10

5:05 a.m.-9:20 a.m.

1 stop6h 15m

C$ 163

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 16 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 C$ 259). Flying from Winnipeg to Oregon in December is currently the most expensive (average of C$ 401). 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.

What is the cheapest time of day to fly from YWG to OR?

Find hourly flight availability from Winnipeg to Oregon. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 14 September 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Oregon as you normally would.

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 14 September 2025.
Check out reviews from past customers who have flown with United Airlines,WestJet, andAir 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.
United Airlines
7.4
Good
8,931 reviews
Check prices

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.
United Airlines
7.4
Good
8,931 reviews
United Airlines
7.4
Good
8,931 reviews
Check prices

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.
WestJet
7.2
Good
3,091 reviews
United Airlines
7.4
Good
8,931 reviews
Check prices

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,931 reviews
Check prices

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.

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 51m. Fly via Delta or Air Canada 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$ 259). Flying from Winnipeg to Oregon in December is currently the most expensive (average of C$ 401). 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 3 airlines flying from Winnipeg to Oregon

Discover the top 3 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 14 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 229AverageC$ 441FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 293AverageC$ 443FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 307AverageC$ 410FlexibilityNo cancel feeOn-time69%
Search United Airlines 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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