HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oregon

$143+ Cheap flights from Winnipeg (YWG) to Oregon

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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to Oregon with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 11, 2025.

Round-trip from

$242
(United Airlines)

One-way from

$143
(Air Canada)

Popular in

June

Cheapest in

August

Average price

$278
From Winnipeg to Oregon
Search Deals
One-way flight from Winnipeg to Oregon
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 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 September 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/174:25 pmYWG - PDX
1 stop6h 41mUnited Airlines
Mon 10/207:35 pmPDX - YWG
2 stops15h 34mUnited Airlines
Deal found 9/11$242
This Air Canada deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/77:10 pmYWG - PDX
1 stop5h 51mAir Canada
Tue 10/143:25 pmPDX - YWG
1 stop8h 37mAir Canada
Deal found 9/10$268
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:00 amYWG - PDX
1 stop11h 58mDelta
Sun 9/2812:45 amPDX - YWG
1 stop9h 09mDelta
Deal found 9/9$294
This Air Canada deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amYWG - PDX
1 stop14h 30mAir Canada
Sun 1/43:15 pmPDX - YWG
1 stop7h 54mAir Canada
Deal found 9/9$314
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/58:30 amYWG - PDX
1 stop6h 35mWestJet
Thu 10/91:45 pmPDX - YWG
1 stop5h 45mWestJet
Deal found 9/10$325
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/712:20 pmYWG - PDX
1 stop10h 06mDelta
Mon 10/1312:40 amPDX - YWG
1 stop8h 50mDelta
Deal found 9/10$352
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/182:20 pmYWG - PDX
1 stop10h 20mUnited Airlines
Thu 1/111:55 pmPDX - YWG
1 stop10h 02mUnited Airlines
Deal found 9/11$372
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:30 amYWG - PDX
2 stops15h 55mMultiple Airlines
Mon 9/291:45 pmPDX - YWG
1 stop17h 16mMultiple Airlines
Deal found 9/9$379

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 2,558,603 searches. Data last updated September 11, 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

Fri 10/17

4:25 pm-10:45 pm

1 stop8h 20m

Portland

Mon 10/20

11:59 pm-3:31 pm

1 stop13h 32m

$242

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 9/26

9:00 am-6:58 pm

1 stop11h 58m

Portland

Sun 9/28

12:45 am-11:54 am

1 stop9h 09m

$294

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 10/7

5:05 am-2:42 pm

2 stops11h 37m

Portland

Tue 10/14

1:44 pm-2:02 am

2 stops10h 18m

$296

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 3/4

10:45 am-2:45 pm

1 stop6h 00m

Portland

Thu 3/5

9:50 am-6:09 pm

1 stop6h 19m

$308

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 12/25

6:00 am-6:30 pm

1 stop14h 30m

Portland

Sun 1/4

3:15 pm-1:09 am

1 stop7h 54m

$314

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 10/5

8:30 am-1:05 pm

1 stop6h 35m

Portland

Thu 10/9

1:45 pm-11:40 pm

2 stops7h 55m

$325

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 9/26

6:30 am-8:25 pm

2 stops15h 55m

Portland

Mon 9/29

1:45 pm-9:01 am

1 stop17h 16m

$379

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 12/18

10:45 am-2:45 pm

1 stop6h 00m

Portland

Thu 1/1

9:50 am-6:09 pm

1 stop6h 19m

$387

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 10/25

5:20 am-9:20 am

1 stop6h 00m

$143

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 10/25

12:15 pm-8:23 am

3 stops22h 08m

$146

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 11 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, November is the cheapest month in which you can book a flight from Winnipeg to Oregon (average of $277). Flying from Winnipeg to Oregon in March is currently the most expensive (average of $368). 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 September 11, 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.

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 September 11, 2025.
Read through reviews of airlines operating flights from Winnipeg to Oregon, such as Air Canada. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,000 reviews

Entertainment

6.8

Boarding

7.3

Comfort

7.1

Crew

7.8

Overall

7.1

Food

6.3

Reviews

1 / 20
8.0
Excellent

Graeme,Sep 2025

YWG - YVR

Why not start boarding from the higher seat numbers? Easier movement for everyone. Easier to put baggage in over head lockers. Unable to get a coffee due to air turbulence, but not offered the chance to have a coffee once it had ceased.
Air Canada
7.1
Good
10,000 reviews
Air Canada
7.1
Good
10,000 reviews

Entertainment

6.8

Boarding

7.3

Comfort

7.1

Crew

7.8

Overall

7.1

Food

6.3

Reviews

1 / 20
8.0
Excellent

Graeme,Sep 2025

YWG - YVR

Why not start boarding from the higher seat numbers? Easier movement for everyone. Easier to put baggage in over head lockers. Unable to get a coffee due to air turbulence, but not offered the chance to have a coffee once it had ceased.

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 4.6 mi from the city center, Winnipeg (YWG) is the airport most travelers 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 20m. Fly via United Airlines, Delta, or Air Canada to get the fastest option. Airlines will cover a distance of 1208 mi. This flight may include one or multiple 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, November is the cheapest month in which you can book a flight from Winnipeg to Oregon (average of $277). Flying from Winnipeg to Oregon in March is currently the most expensive (average of $368). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Oregon

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Las Vegas flights
Winnipeg to O'Hare Intl flights
Winnipeg to Seattle flights
Winnipeg to Orlando flights
Winnipeg to Minneapolis flights
Winnipeg to Newark flights
Winnipeg to John F Kennedy Intl flights
Winnipeg to LaGuardia flights
Winnipeg to Fort Lauderdale flights
Winnipeg to Los Angeles flights
Winnipeg to Miami flights
Winnipeg to Sky Harbor Intl flights
Winnipeg to Ontario flights
Winnipeg to Midway flights
Winnipeg to Nashville flights
Winnipeg to Dallas/Fort Worth flights
Winnipeg to Palm Springs flights
Winnipeg to Dulles Intl flights
Winnipeg to San Diego flights
Winnipeg to San Francisco flights
Winnipeg to Santa Ana flights
Winnipeg to George Bush Intcntl flights
Winnipeg to Hobby flights
Winnipeg to Denver flights
Winnipeg to Honolulu flights
Winnipeg to Reagan-National flights
Winnipeg to Sacramento flights
Winnipeg to Baltimore flights
Winnipeg to Portland flights
Winnipeg to New Orleans flights
Winnipeg to Detroit flights
Winnipeg to Atlanta flights
Winnipeg to Burbank flights
Winnipeg to Philadelphia flights
Winnipeg to Fort Myers flights
Winnipeg to St. Louis flights
Winnipeg to Boston flights
Winnipeg to Kansas City flights
Winnipeg to Anchorage flights
Winnipeg to Tampa flights
Winnipeg to Love Field flights
Winnipeg to Kahului flights
Winnipeg to Traverse City flights
Winnipeg to Charlotte flights
Winnipeg to Memphis flights
Winnipeg to San Jose flights
Winnipeg to Pittsburgh flights
Winnipeg to Reno flights
Winnipeg to Akron flights
Winnipeg to Columbus flights

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 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$214Average$330FlexibilityNo cancel feeOn-time67%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.