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$210+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

This Justfly.com deal was found by Cheapflights users on 12/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/195:45 pmYWG - PDX
1 stop21h 15mWestJet
Fri 1/96:00 amPDX - YWG
1 stop27h 03mWestJet
Deal found 12/12$508
This Air Canada deal was found by Cheapflights users on 12/14. 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 12/186:00 amYWG - PDX
1 stop10h 40mAir Canada
Thu 1/13:15 pmPDX - YWG
1 stop7h 59mAir Canada
Deal found 12/14$546
This FlightHub deal was found by Cheapflights users on 12/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/192:40 pmYWG - PDX
2 stops28h 00mMultiple Airlines
Fri 1/91:38 pmPDX - YWG
2 stops9h 01mMultiple Airlines
Deal found 12/12$576
This FlightHub deal was found by Cheapflights users on 12/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:45 amYWG - PDX
2 stops12h 58mWestJet
Thu 1/112:29 pmPDX - YWG
2 stops10h 12mWestJet
Deal found 12/14$580
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Tue 12/237:50 amYWG - PDX
2 stops33h 10mMultiple Airlines
Sat 1/105:32 pmPDX - YWG
1 stop29h 11mMultiple Airlines
Deal found 12/14$613
This Air Canada deal was found by Cheapflights users on 12/14. 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 12/239:40 pmYWG - PDX
1 stop13h 35mAir Canada
Sat 1/109:50 amPDX - YWG
1 stop6h 19mAir Canada
Deal found 12/14$639
This WestJet deal was found by Cheapflights users on 12/14. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/232:40 pmYWG - PDX
2 stops27h 44mWestJet
Sat 1/109:20 amPDX - YWG
2 stops13h 21mWestJet
Deal found 12/14$659
This United Airlines deal was found by Cheapflights users on 12/14. 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.
Tue 12/232:20 pmYWG - PDX
3 stops30h 28mUnited Airlines
Sat 1/105:00 amPDX - YWG
2 stops28h 57mUnited Airlines
Deal found 12/14$977
This American Airlines deal was found by Cheapflights users on 12/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amYWG - PDX
3 stops19h 06mAmerican Airlines
Fri 1/96:00 amPDX - YWG
2 stops15h 35mAmerican Airlines
Deal found 12/12$1,067
This American Airlines deal was found by Cheapflights users on 12/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:00 amYWG - PDX
3 stops17h 19mAmerican Airlines
Sat 1/106:22 pmPDX - YWG
3 stops27h 13mAmerican Airlines
Deal found 12/14$1,154

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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$353
(Delta)

One-way from

$210
(Kiwi.com)

Popular in

June

Cheapest in

August

Average price

$351
Provider with most accurate pricing for Winnipeg-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Portland flights.
Search Deals
From Winnipeg to Oregon
Search Deals
One-way flight from Winnipeg to Oregon
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 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 2,558,603 searches. Data last updated December 15, 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 3/1

11:53 am-8:30 pm

1 stop10h 37m

Portland

Tue 3/3

12:40 am-11:01 am

1 stop8h 21m

$353

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 3/26

10:10 pm-9:15 am

1 stop13h 05m

Portland

Sun 3/29

3:15 pm-1:14 am

1 stop7h 59m

$357

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 2/9

10:40 am-6:30 pm

1 stop9h 50m

Portland

Mon 2/16

7:05 pm-12:59 pm

1 stop15h 54m

$376

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 3/1

8:00 am-6:30 pm

2 stops12h 30m

Portland

Wed 3/4

3:15 pm-1:14 am

1 stop7h 59m

$387

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Thu 1/15

2:20 pm-12:14 pm

2 stops23h 54m

Medford

Sun 1/18

12:55 pm-11:57 am

2 stops21h 02m

$735

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Thu 1/15

6:40 am-10:57 pm

2 stops18h 17m

Medford

Sun 1/18

3:00 pm-11:38 pm

2 stops30h 38m

$755

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 1/7

7:50 am-8:47 pm

3 stops14h 57m

$210

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 1/7

6:00 am-6:30 pm

1 stop14h 30m

$213

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 1/5

8:00 am-9:30 am

1 stop27h 30m

$249

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 1/6

6:15 am-1:30 pm

2 stops33h 15m

$273

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

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 $140). Flying from Winnipeg to Oregon in June is currently the most expensive (average of $348). 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 December 15, 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 afternoon, which can drop the price by up to 47% versus a flight at noon.

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 December 15, 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
10,525 reviews

Comfort

7.1

Overall

7.1

Food

6.3

Boarding

7.3

Entertainment

6.8

Crew

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍
Air Canada
7.1
Good
10,525 reviews
Air Canada
7.1
Good
10,525 reviews

Comfort

7.1

Overall

7.1

Food

6.3

Boarding

7.3

Entertainment

6.8

Crew

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍

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 10h 37m. Fly via Delta, Air Canada, or United Airlines 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, August is the cheapest month in which you can book a flight from Winnipeg to Oregon (average of $140). Flying from Winnipeg to Oregon in June is currently the most expensive (average of $348). 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 2,558,603 searches. Data last updated December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$214Average$330FlexibilityNo cancel feeOn-time67%

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