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Cheap flights from Oregon to Winnipeg from C$ 226

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 20/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
28 Jul — 4 Aug1
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 28 June 2026.

Tue 28/72:30 p.m.
PDX
-
YWG
2 stops16h 50m
WestJet
Tue 4/810:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 27/6C$ 478
Thu 30/72:30 p.m.
PDX
-
YWG
2 stops16h 50m
WestJet
Tue 4/810:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 27/6C$ 488
Sat 26/93:30 p.m.
PDX
-
YWG
1 stop6h 25m
Air Canada
Sat 3/105:45 a.m.
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 27/6C$ 497
Sat 26/94:07 p.m.
PDX
-
YWG
2 stops18h 30m
Multiple Airlines
Sat 3/105:45 a.m.
YWG
-
PDX
1 stop5h 46m
Multiple Airlines
Deal found 27/6C$ 517
Thu 23/77:45 p.m.
PDX
-
YWG
1 stop5h 17m
Air Canada
Sun 26/75:45 a.m.
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 24/6C$ 518
Sat 29/810:10 a.m.
PDX
-
YWG
1 stop5h 37m
Air Canada
Mon 31/87:20 a.m.
YWG
-
PDX
2 stops9h 31m
Air Canada
Deal found 26/6C$ 525
Mon 24/87:45 p.m.
PDX
-
YWG
1 stop5h 12m
Air Canada
Tue 25/87:20 a.m.
YWG
-
PDX
2 stops9h 31m
Air Canada
Deal found 24/6C$ 527
Thu 30/72:30 p.m.
PDX
-
YWG
2 stops16h 50m
WestJet
Mon 3/812:00 p.m.
YWG
-
PDX
1 stop27h 50m
WestJet
Deal found 27/6C$ 529

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 28 June 2026.

Round-trip from

C$ 478

One-way from

C$ 226

Popular in

February

Cheapest in

November

Average price

C$ 1,186
WestJet
  • WestJet
  • 28/7-4/8
  • 3 total stops
  • 22h 30m total
  • Oregon to Winnipeg
Search Deals
Air Canada
  • Air Canada
  • 11/7
  • 1 total stop
  • 5h 17m total
  • Oregon to Winnipeg
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 177 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 66 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 28 June 2026.
Use the filters below to find and compare flights from Oregon to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 30/7

7:45 p.m.-3:02 a.m.

1 stop5h 17m

Winnipeg

Wed 5/8

5:45 a.m.-9:31 a.m.

1 stop5h 46m

C$ 518
Quickest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 20/8

7:45 p.m.-2:57 a.m.

1 stop5h 12m

Winnipeg

Mon 24/8

5:45 a.m.-9:31 a.m.

1 stop5h 46m

C$ 518

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 29/8

8:17 a.m.-10:33 p.m.

1 stop12h 16m

Winnipeg

Mon 31/8

7:00 a.m.-10:52 p.m.

1 stop17h 52m

C$ 539

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 15/8

12:35 a.m.-11:54 a.m.

1 stop9h 19m

Winnipeg

Sun 23/8

12:46 p.m.-8:17 p.m.

1 stop9h 31m

C$ 563

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 24/8

7:45 p.m.-2:57 a.m.

1 stop5h 12m

Winnipeg

Tue 25/8

7:20 a.m.-2:51 p.m.

2 stops9h 31m

C$ 566

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 1/8

5:00 a.m.-10:38 p.m.

2 stops15h 38m

Winnipeg

Mon 10/8

9:00 p.m.-9:31 a.m.

1 stop14h 31m

C$ 613

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 20/8

8:24 p.m.-11:54 a.m.

2 stops13h 30m

Winnipeg

Mon 24/8

3:58 p.m.-11:20 p.m.

1 stop9h 22m

C$ 707
Cheapest one-way
Quickest one-way

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 20/8

7:45 p.m.-2:57 a.m.

1 stop5h 12m

C$ 226

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 11/7

4:15 p.m.-11:52 a.m.

2 stops17h 37m

C$ 240

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 13/10

11:39 a.m.-11:34 p.m.

1 stop9h 55m

C$ 244

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/6

Showing 1-10 of 13 resultsSorted by cheapest first
1
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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 month to book a flight from Oregon to Winnipeg?

Currently, November is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of C$ 261). Flying from Oregon to Winnipeg in April is currently the most expensive (average of C$ 905). 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.

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?

    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, United Airlines, and Delta can get you from Oregon to Winnipeg in just under 5h 17m. Your travel time can differ by up to 6h 59m. Oregon and Winnipeg are separated by a distance of 1944 km. 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.

  • What is the cheapest month to book a flight from Oregon to Winnipeg?

    Currently, November is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of C$ 261). Flying from Oregon to Winnipeg in April is currently the most expensive (average of C$ 905). 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

Travelling to a place near Winnipeg?

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

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