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Cheap flights from Portland to Winnipeg from C$ 229

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 13/5. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
11 Apr — 18 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Portland to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Portland to Winnipeg
Explore the most affordable flight options available from Portland to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 March 2026.

Sun 10/52:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Sun 17/510:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 10/3C$ 433
Wed 13/52:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Sun 17/510:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 10/3C$ 437
Mon 15/62:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Tue 16/610:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 11/3C$ 458
Sun 10/52:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Tue 19/57:00 a.m.
YWG
-
PDX
2 stops8h 50m
WestJet
Deal found 10/3C$ 471
Sun 10/52:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Wed 20/56:00 a.m.
YWG
-
PDX
1 stop9h 50m
WestJet
Deal found 10/3C$ 475
Mon 11/52:30 p.m.
PDX
-
YWG
1 stop8h 25m
WestJet
Thu 21/510:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 10/3C$ 477
Thu 11/62:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Tue 16/610:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 11/3C$ 479
Wed 29/43:15 p.m.
PDX
-
YWG
1 stop7h 59m
Air Canada
Sun 3/55:45 a.m.
YWG
-
PDX
1 stop5h 45m
Air Canada
Deal found 8/3C$ 483
Fri 8/52:30 p.m.
PDX
-
YWG
2 stops22h 10m
WestJet
Tue 19/510:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 10/3C$ 485
Wed 13/52:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Sat 16/57:10 p.m.
YWG
-
PDX
1 stop20h 40m
WestJet
Deal found 10/3C$ 487

Find flight deals from Portland to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 12 March 2026.

Round-trip from

C$ 433

One-way from

C$ 229

Popular in

February

Cheapest in

November

Average price

C$ 667
WestJet
  • WestJet
  • 10/5-19/5
  • 2 total stops
  • 11h 20m total
  • Portland to Winnipeg
Search Deals
United Airlines
  • United Airlines
  • 13/5
  • 1 total stop
  • 9h 57m total
  • Portland to Winnipeg
Search Deals
Highest demand for flights based on searches. 28% potential increase in price (C$ 304 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease (C$ 86 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland 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 12 March 2026.
Use the filters below to find and compare flights from Portland to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 15/5

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

2 stops16h 50m

Winnipeg

Mon 18/5

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

1 stop8h 50m

C$ 496
Quickest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 14/5

3:30 p.m.-2:04 a.m.

1 stop8h 34m

Winnipeg

Sun 17/5

5:45 a.m.-9:30 a.m.

1 stop5h 45m

C$ 509

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 29/4

3:15 p.m.-1:14 a.m.

1 stop7h 59m

Winnipeg

Sun 3/5

5:45 a.m.-7:05 p.m.

1 stop15h 20m

C$ 509

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 11/5

10:55 p.m.-11:52 a.m.

1 stop10h 57m

Winnipeg

Sat 16/5

8:45 a.m.-5:44 p.m.

1 stop10h 59m

C$ 519

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 15/5

11:55 p.m.-11:52 a.m.

1 stop9h 57m

Winnipeg

Tue 19/5

8:45 a.m.-12:33 a.m.

2 stops17h 48m

C$ 531

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 13/5

1:37 p.m.-11:52 a.m.

2 stops20h 15m

Winnipeg

Thu 14/5

2:00 p.m.-11:55 p.m.

1 stop11h 55m

C$ 531

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 12/5

11:55 p.m.-11:52 a.m.

1 stop9h 57m

Winnipeg

Tue 19/5

8:45 a.m.-12:33 a.m.

2 stops17h 48m

C$ 531

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 1/5

11:55 p.m.-11:52 a.m.

1 stop9h 57m

Winnipeg

Sun 10/5

2:00 p.m.-10:35 p.m.

1 stop10h 35m

C$ 532

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 16/5

11:55 p.m.-11:52 a.m.

1 stop9h 57m

Winnipeg

Mon 18/5

8:45 a.m.-9:09 p.m.

1 stop14h 24m

C$ 532

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 20/4

12:30 a.m.-10:56 a.m.

1 stop8h 26m

Winnipeg

Tue 28/4

11:55 a.m.-8:07 p.m.

1 stop10h 12m

C$ 604

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/3

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

Best time to book a flight from Portland to Winnipeg

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

What’s the top layover airport for flights from Portland to Winnipeg?

Share of one-stop round-trip flights from Portland to Winnipeg chosen by Cheapflights users in the past 12 months, using the same layover each way.

Calgary (YYC) – chosen by Cheapflights users on 80% of one-stop itineraries from Portland to Winnipeg on Cheapflights.

What’s the cheapest layover airport for flights from Portland to Winnipeg?

Average round-trip fare for 1-stop flights from Portland to Winnipeg, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of C$ 381.

What’s the fastest layover option from Portland to Winnipeg?

Shortest average travel time for 1-stop one-way flights from Portland to Winnipeg, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 6h 09m.

Which airport typically offers the quickest layover for flights from Portland to Winnipeg?

Average layover duration for 1-stop one-way flights from Portland to Winnipeg, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 1h 18m.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated 12 March 2026.
Read through reviews of airlines operating flights from Portland to Winnipeg, such as WestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,291 reviews
Check prices

Food

6.2

Comfort

7.0

Overall

7.2

Entertainment

6.1

Boarding

7.4

Crew

7.9

Reviews

1 / 20
4.0
Okay

Josh,Nov 2025

LAS - YEG

Very cramped seats, incredibly poor customer service when arriving at the airport.
WestJet
7.2
Good
3,291 reviews
WestJet
7.2
Good
3,291 reviews
Check prices

Food

6.2

Comfort

7.0

Overall

7.2

Entertainment

6.1

Boarding

7.4

Crew

7.9

Reviews

1 / 20
4.0
Okay

Josh,Nov 2025

LAS - YEG

Very cramped seats, incredibly poor customer service when arriving at the airport.

Related info for your journey

Find useful and relevant information for your journey from Portland to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Portland to Winnipeg?

    A quick flight from Portland to Winnipeg can take about 8h 34m. WestJet provides one of the quickest options available for as low as C$ 509. The distance from Portland to Winnipeg is about 1944 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What is the cheapest airline to fly from Portland to Winnipeg round-trip?

    Cheapflights users have booked flights from Portland to Winnipeg round-trip from C$ 240. WestJet is 57% cheaper than the average price of flights available within the next 90 days to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland 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

Browse thousands of different options on Cheapflights for your next trip

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Complete your trip

Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
Winnipeg car rentals
Winnipeg Airport car rentals
Brandon car rentals
Thompson car rentals

Top airline flying from Portland to Winnipeg

Discover the top airline that operate flights from Portland 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 12 March 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 240AverageC$ 293FlexibilityNo 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 Portland to Winnipeg?

Cheapflights makes it easy to find Portland to Winnipeg flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

Millions of users choose and trust Cheapflights to book the best flight deals from Portland to Winnipeg for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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

Users can book flights with no change fees policies with our dedicated filters. Book flights from Portland to Winnipeg flexibly with Cheapflights today.

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

Of course! You can now track prices for flights from Portland to Winnipeg and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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