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Cheap flights from Winnipeg to Oregon from C$ 289

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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
14 Jan — 21 Jan1
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 15 December 2025.

Fri 19/125:45 p.m.YWG - PDX
1 stop21h 15mWestJet
Fri 9/16:00 a.m.PDX - YWG
1 stop27h 03mWestJet
Deal found 12/12C$ 699
Thu 18/126:00 a.m.YWG - PDX
1 stop14h 30mAir Canada
Thu 1/13:15 p.m.PDX - YWG
1 stop7h 59mAir Canada
Deal found 15/12C$ 752
Fri 19/122:40 p.m.YWG - PDX
2 stops28h 00mMultiple Airlines
Fri 9/11:38 p.m.PDX - YWG
2 stops9h 01mMultiple Airlines
Deal found 12/12C$ 793
Thu 18/126:45 a.m.YWG - PDX
2 stops12h 58mWestJet
Thu 1/112:29 p.m.PDX - YWG
2 stops10h 12mWestJet
Deal found 15/12C$ 799
Tue 23/127:50 a.m.YWG - PDX
2 stops33h 10mMultiple Airlines
Sat 10/15:32 p.m.PDX - YWG
1 stop29h 11mMultiple Airlines
Deal found 14/12C$ 844
Tue 23/129:40 p.m.YWG - PDX
1 stop13h 35mAir Canada
Sat 10/19:50 a.m.PDX - YWG
1 stop6h 19mAir Canada
Deal found 14/12C$ 880
Tue 23/122:40 p.m.YWG - PDX
2 stops27h 44mWestJet
Sat 10/19:20 a.m.PDX - YWG
2 stops13h 21mWestJet
Deal found 14/12C$ 907
Tue 23/122:20 p.m.YWG - PDX
3 stops30h 28mUnited Airlines
Sat 10/15:00 a.m.PDX - YWG
2 stops28h 57mUnited Airlines
Deal found 14/12C$ 1,345
Fri 19/126:00 a.m.YWG - PDX
3 stops19h 06mAmerican Airlines
Fri 9/16:00 a.m.PDX - YWG
2 stops15h 35mAmerican Airlines
Deal found 12/12C$ 1,469
Tue 23/126:00 a.m.YWG - PDX
3 stops17h 19mAmerican Airlines
Sat 10/16:22 p.m.PDX - YWG
3 stops27h 13mAmerican Airlines
Deal found 14/12C$ 1,589

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 15 December 2025.

Round-trip from

C$ 486

One-way from

C$ 289

Popular in

June

Cheapest in

August

Average price

C$ 483
Delta
  • Delta
  • 1/3-3/3
  • 2 total stops
  • 18h 58m total
  • Winnipeg to Oregon
Search Deals
7/1
  • 7/1
  • 3 total stops
  • 14h 57m total
  • Winnipeg to Oregon
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 15 December 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

Sun 1/3

11:53 a.m.-8:30 p.m.

1 stop10h 37m

Portland

Tue 3/3

12:40 a.m.-11:01 a.m.

1 stop8h 21m

C$ 486

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 26/3

10:10 p.m.-9:15 a.m.

1 stop13h 05m

Portland

Sun 29/3

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

1 stop7h 59m

C$ 492

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 9/2

10:40 a.m.-6:30 p.m.

1 stop9h 50m

Portland

Mon 16/2

7:05 p.m.-12:59 p.m.

1 stop15h 54m

C$ 518

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 1/3

8:00 a.m.-6:30 p.m.

2 stops12h 30m

Portland

Wed 4/3

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

1 stop7h 59m

C$ 533

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Thu 15/1

2:20 p.m.-12:14 p.m.

2 stops23h 54m

Medford

Sun 18/1

12:55 p.m.-11:57 a.m.

2 stops21h 02m

C$ 1,012

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Thu 15/1

6:40 a.m.-10:57 p.m.

2 stops18h 17m

Medford

Sun 18/1

3:00 p.m.-11:38 p.m.

2 stops30h 38m

C$ 1,040

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 7/1

7:50 a.m.-8:47 p.m.

3 stops14h 57m

C$ 289

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 7/1

6:00 a.m.-6:30 p.m.

1 stop14h 30m

C$ 293

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 5/1

8:00 a.m.-9:30 a.m.

1 stop27h 30m

C$ 343

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 6/1

6:15 a.m.-1:30 p.m.

2 stops33h 15m

C$ 376

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/12

Showing 1-10 of 12 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$ 193). Flying from Winnipeg to Oregon in June is currently the most expensive (average of C$ 479). 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 15 December 2025.

When flying from Winnipeg to Oregon, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 69% versus a flight in the afternoon.

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 15 December 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
9,092 reviews
Check prices

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2025

AMS - EWR

It was good! The first 3/4 of the trip was uncomfortably cold. Only one option for lunch that I didn’t enjoy (vegetarian).
United Airlines
7.4
Good
9,092 reviews
United Airlines
7.4
Good
9,092 reviews
Check prices

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2025

AMS - EWR

It was good! The first 3/4 of the trip was uncomfortably cold. Only one option for lunch that I didn’t enjoy (vegetarian).
WestJet
7.2
Good
3,202 reviews
United Airlines
7.4
Good
9,092 reviews
Check prices

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2025

AMS - EWR

It was good! The first 3/4 of the trip was uncomfortably cold. Only one option for lunch that I didn’t enjoy (vegetarian).
Air Canada
7.1
Good
10,525 reviews
United Airlines
7.4
Good
9,092 reviews
Check prices

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2025

AMS - EWR

It was good! The first 3/4 of the trip was uncomfortably cold. Only one option for lunch that I didn’t enjoy (vegetarian).

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 10h 37m. Fly via Delta, 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$ 193). Flying from Winnipeg to Oregon in June is currently the most expensive (average of C$ 479). 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 15 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 227AverageC$ 439FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 305AverageC$ 420FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 321AverageC$ 440FlexibilityNo 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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