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$323+ Cheap flights from Oregon to Winnipeg (YWG)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Oregon to Winnipeg

Cheapest flights from Oregon to Winnipeg
Explore the most affordable flight options available from Oregon to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 15, 2025.

This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:54 pmPDX - YWG
1 stop5h 57mUnited Airlines
Mon 12/298:40 amYWG - PDX
1 stop16h 19mUnited Airlines
Deal found 12/12$717
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.
Mon 12/156:15 amPDX - YWG
1 stop27h 30mWestJet
Sun 12/212:40 pmYWG - PDX
2 stops28h 00mWestJet
Deal found 12/14$773
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.
Thu 12/2512:29 pmPDX - YWG
2 stops8h 12mWestJet
Mon 12/295:55 amYWG - PDX
2 stops31h 10mWestJet
Deal found 12/12$818
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.
Mon 12/159:50 amPDX - YWG
1 stop6h 19mAir Canada
Sun 12/219:40 pmYWG - PDX
1 stop13h 35mAir Canada
Deal found 12/14$870
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.
Thu 12/182:05 pmPDX - YWG
1 stop8h 29mMultiple Airlines
Sat 12/208:30 pmYWG - PDX
2 stops16h 23mMultiple Airlines
Deal found 12/14$889
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 12/189:50 amPDX - YWG
1 stop6h 19mAir Canada
Sat 12/209:40 pmYWG - PDX
1 stop13h 35mAir Canada
Deal found 12/14$895
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.
Mon 12/1511:59 pmPDX - YWG
1 stop9h 58mUnited Airlines
Sun 12/218:40 amYWG - PDX
1 stop16h 19mUnited Airlines
Deal found 12/14$923
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.
Thu 12/185:00 amPDX - YWG
2 stops28h 57mUnited Airlines
Sat 12/202:20 pmYWG - PDX
2 stops21h 41mUnited Airlines
Deal found 12/14$971
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.
Thu 12/2510:21 pmPDX - YWG
2 stops23h 14mAmerican Airlines
Mon 12/296:00 amYWG - PDX
3 stops16h 54mAmerican Airlines
Deal found 12/12$1,505

Find flight deals from Oregon to Winnipeg

Keep the following information in mind while searching for Oregon to Winnipeg flight deals. Data was last updated December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$323
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$574
Provider with most accurate pricing for Portland-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Winnipeg flights.
Search Deals
From Oregon to Winnipeg
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($76 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($24 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 Oregon to Winnipeg 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 Oregon to Winnipeg that are best for you.

Fly from

Oregon

Fly to

Winnipeg

Route

Depart

Return

Price

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 1/29

1:38 pm-1:52 pm

2 stops22h 14m

Winnipeg

Thu 2/5

7:30 am-9:49 am

1 stop28h 19m

$323

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 1/12

9:50 am-6:09 pm

1 stop6h 19m

Winnipeg

Thu 1/15

10:45 am-2:40 pm

1 stop5h 55m

$418

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 1/12

1:24 pm-11:57 am

2 stops20h 33m

Winnipeg

Thu 1/15

2:20 pm-10:32 pm

1 stop10h 12m

$437

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 1/29

5:35 am-1:14 am

2 stops17h 39m

Winnipeg

Thu 2/5

10:40 am-11:06 pm

2 stops14h 26m

$537

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 12/25

12:54 pm-8:51 pm

1 stop5h 57m

Winnipeg

Mon 12/29

8:40 am-10:59 pm

1 stop16h 19m

$717

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Best time to book a flight from Oregon to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Oregon 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 Oregon to Winnipeg

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

Find hourly flight availability from Oregon to Winnipeg. 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 Oregon to Winnipeg, 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 48% versus a flight in the morning.

How much does it cost to fly round-trip from Oregon to Winnipeg?

Related info for your journey

Find useful and relevant information for your journey from Oregon to Winnipeg. 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 into for flights to Winnipeg from Oregon?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Oregon. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • How long is the flight from Oregon to Winnipeg?

    Air Canada and United Airlines can get you from Oregon to Winnipeg in just under 6h 19m. Your travel time can differ by up to 14h 14m. The distance between Oregon and Winnipeg is about 1208 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Oregon to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Oregon to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Winnipeg.

  • Can I find deals for business class flights from Oregon to Winnipeg?

    Yes. Cheapflights offers flight deals from Oregon to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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Top 3 airlines flying from Oregon to Winnipeg

Discover the top 3 airlines that operate flights from Oregon to Winnipeg. 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
WestJetCheapest$135Average$328FlexibilityNo cancel feeOn-time60%
DeltaCheapest$160Average$472FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$175Average$335FlexibilityNo cancel feeOn-time67%

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