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Cheap flights from Oregon to Winnipeg from C$ 444

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 29/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
15 Jan — 22 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Oregon to Winnipeg

Enter your travel dates to find the best prices.

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 16 December 2025.

Wed 31/123:15 p.m.PDX - YWG
1 stop7h 59mAir Canada
Mon 5/19:50 p.m.YWG - PDX
1 stop13h 25mAir Canada
Deal found 16/12C$ 619
Wed 31/1212:29 p.m.PDX - YWG
2 stops8h 12mMultiple Airlines
Mon 5/18:00 a.m.YWG - PDX
1 stop27h 30mMultiple Airlines
Deal found 15/12C$ 786
Wed 31/127:45 p.m.PDX - YWG
2 stops14h 12mUnited Airlines
Mon 5/12:20 p.m.YWG - PDX
1 stop10h 20mUnited Airlines
Deal found 16/12C$ 841
Wed 31/1212:29 p.m.PDX - YWG
2 stops10h 12mWestJet
Mon 5/112:55 p.m.YWG - PDX
2 stops33h 17mWestJet
Deal found 15/12C$ 903
Wed 31/1212:29 p.m.PDX - YWG
2 stops10h 12mWestJet
Sun 4/12:40 p.m.YWG - PDX
2 stops24h 04mWestJet
Deal found 15/12C$ 950
Wed 31/1212:29 p.m.PDX - YWG
2 stops8h 12mMultiple Airlines
Sun 4/14:55 p.m.YWG - PDX
1 stop28h 55mMultiple Airlines
Deal found 15/12C$ 956
Fri 26/1212:16 p.m.PDX - YWG
1 stop9h 28mWestJet
Thu 1/18:05 p.m.YWG - PDX
2 stops41h 00mWestJet
Deal found 15/12C$ 1,035
Fri 26/1211:55 p.m.PDX - YWG
1 stop10h 02mUnited Airlines
Thu 1/18:40 a.m.YWG - PDX
1 stop16h 19mUnited Airlines
Deal found 15/12C$ 1,057
Mon 15/126:15 a.m.PDX - YWG
1 stop27h 30mWestJet
Sun 21/122:40 p.m.YWG - PDX
2 stops28h 00mWestJet
Deal found 14/12C$ 1,064

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 16 December 2025.

Round-trip from

C$ 444

Popular in

December

Cheapest in

February

Average price

C$ 790
29/1-5/2
  • 29/1-5/2
  • 3 total stops
  • 50h 33m total
  • Oregon to Winnipeg
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 143 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 47 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 629,999 searches. Data last updated 16 December 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 29/1

1:38 p.m.-1:52 p.m.

2 stops22h 14m

Winnipeg

Thu 5/2

7:30 a.m.-9:49 a.m.

1 stop28h 19m

C$ 444

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 12/1

9:50 a.m.-6:09 p.m.

1 stop6h 19m

Winnipeg

Thu 15/1

10:45 a.m.-2:40 p.m.

1 stop5h 55m

C$ 575

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 12/1

1:24 p.m.-11:57 a.m.

2 stops20h 33m

Winnipeg

Thu 15/1

2:20 p.m.-10:32 p.m.

1 stop10h 12m

C$ 601

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 29/1

5:35 a.m.-1:14 a.m.

2 stops17h 39m

Winnipeg

Thu 5/2

10:40 a.m.-11:06 p.m.

2 stops14h 26m

C$ 739

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 31/12

7:45 p.m.-11:57 a.m.

2 stops14h 12m

Winnipeg

Mon 5/1

2:20 p.m.-10:40 p.m.

1 stop10h 20m

C$ 841

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/12

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
No data available for this route at this time. Please check back soon.

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?

    For a flight from Oregon to Winnipeg, you will be flying into Winnipeg. Winnipeg (YWG) is just 7.3 km from the centre of the city.

  • How long is the flight from Oregon to Winnipeg?

    Air Canada can get you from Oregon to Winnipeg in just under 6h 19m. Your travel time can differ by up to . Oregon and Winnipeg are separated by a distance of 1944 km.

  • 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

Travelling to a place near Winnipeg?

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

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Top airline flying from Oregon to Winnipeg

Discover the top airline 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 629,999 searches. Data last updated 16 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 243AverageC$ 297FlexibilityNo cancel feeOn-time60%
Search WestJet 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 Oregon to Winnipeg?

Cheapflights helps you search for flights from Oregon to Winnipeg via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Oregon to Winnipeg?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Oregon to Winnipeg for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Oregon to Winnipeg with no change fees?

Yes! Cheapflights helps users easily find flights from Oregon to Winnipeg with no change fees.

Can Cheapflights notify me if prices for flights from Oregon to Winnipeg become cheaper?

Not ready to book yet? You can track prices for flights from Oregon to Winnipeg on Cheapflights with our Price Alert feature and get notified when better prices are available.

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