Find flights
When to book
FAQs

Cheap flights from Oregon to Winnipeg from C$ 239

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 26/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
8 Jun — 15 Jun1
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 9 May 2026.

Thu 20/82:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Tue 25/810:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 7/5C$ 353
Wed 12/82:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Wed 26/810:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 6/5C$ 354
Sun 16/82:30 p.m.
PDX
-
YWG
1 stop7h 10m
WestJet
Mon 24/810:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 4/5C$ 359
Thu 13/82:30 p.m.
PDX
-
YWG
1 stop7h 10m
WestJet
Tue 25/87:00 a.m.
YWG
-
PDX
2 stops8h 50m
WestJet
Deal found 4/5C$ 361
Thu 13/82:30 p.m.
PDX
-
YWG
1 stop7h 10m
WestJet
Mon 24/810:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 4/5C$ 373
Mon 17/82:30 p.m.
PDX
-
YWG
1 stop7h 10m
WestJet
Sun 23/810:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 4/5C$ 385
Sun 16/82:30 p.m.
PDX
-
YWG
1 stop7h 10m
WestJet
Sun 23/810:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 5/5C$ 387
Fri 14/82:30 p.m.
PDX
-
YWG
1 stop7h 10m
WestJet
Tue 25/810:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 4/5C$ 410

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 9 May 2026.

Round-trip from

C$ 353

One-way from

C$ 239

Popular in

February

Cheapest in

November

Average price

C$ 584
WestJet
  • WestJet
  • 20/8-25/8
  • 2 total stops
  • 11h 20m total
  • Oregon to Winnipeg
Search Deals
WestJet
  • WestJet
  • 26/8
  • 1 total stop
  • 5h 40m total
  • Oregon to Winnipeg
Search Deals
Highest demand for flights based on searches. 24% potential increase in price (C$ 276 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease (C$ 73 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 9 May 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

Wed 12/8

2:30 p.m.-10:10 p.m.

1 stop5h 40m

Winnipeg

Wed 26/8

6:00 a.m.-1:50 p.m.

2 stops9h 50m

C$ 392
Quickest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 19/10

10:10 a.m.-5:47 p.m.

1 stop5h 37m

Winnipeg

Thu 22/10

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

1 stop5h 46m

C$ 446

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 26/8

3:30 p.m.-2:57 a.m.

1 stop9h 27m

Winnipeg

Sat 29/8

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

2 stops9h 31m

C$ 465

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 6/6

3:30 p.m.-11:49 p.m.

1 stop6h 19m

Winnipeg

Mon 8/6

10:55 a.m.-2:45 p.m.

1 stop5h 50m

C$ 492

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 16/8

6:00 a.m.-4:52 p.m.

1 stop8h 52m

Winnipeg

Sun 23/8

3:58 p.m.-11:25 p.m.

1 stop9h 27m

C$ 496

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 28/5

2:30 p.m.-12:55 a.m.

1 stop8h 25m

Winnipeg

Sat 30/5

10:10 a.m.-1:50 p.m.

1 stop5h 40m

C$ 581

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 25/5

11:58 a.m.-11:26 p.m.

1 stop9h 28m

Winnipeg

Mon 8/6

5:41 p.m.-11:18 p.m.

1 stop7h 37m

C$ 597

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 27/5

11:58 a.m.-11:26 p.m.

1 stop9h 28m

Winnipeg

Mon 8/6

3:54 p.m.-11:18 p.m.

1 stop9h 24m

C$ 597

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 6/6

9:20 a.m.-11:26 p.m.

2 stops12h 06m

Winnipeg

Mon 8/6

6:40 a.m.-10:39 a.m.

1 stop5h 59m

C$ 644

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 26/5

2:30 p.m.-9:20 a.m.

2 stops16h 50m

Winnipeg

Fri 29/5

7:00 a.m.-1:50 p.m.

2 stops8h 50m

C$ 645

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

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, July is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of C$ 120). Flying from Oregon to Winnipeg in April is currently the most expensive (average of C$ 872). 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?

    WestJet and Air Canada can get you from Oregon to Winnipeg in just under 5h 37m. Your travel time can differ by up to 03m. 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, July is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of C$ 120). Flying from Oregon to Winnipeg in April is currently the most expensive (average of C$ 872). 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

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.

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.

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.