Find flights
When to book
FAQs

Cheap flights from Portland to Winnipeg from C$ 259

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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
11 Jul — 18 Jul1
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 11 June 2026.

Wed 9/92:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Mon 21/910:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 9/6C$ 474
Wed 9/92:30 p.m.
PDX
-
YWG
1 stop7h 10m
WestJet
Fri 11/910:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 9/6C$ 507
Sun 13/92:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Sun 20/99:05 p.m.
YWG
-
PDX
1 stop18h 45m
WestJet
Deal found 9/6C$ 516
Wed 8/72:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Tue 14/72:55 p.m.
YWG
-
PDX
1 stop24h 55m
WestJet
Deal found 8/6C$ 530
Wed 9/93:30 p.m.
PDX
-
YWG
1 stop6h 10m
Air Canada
Sat 12/95:45 a.m.
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 9/6C$ 534
Thu 10/92:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Sat 12/910:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 9/6C$ 537
Wed 9/92:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Thu 10/97:00 a.m.
YWG
-
PDX
2 stops8h 50m
WestJet
Deal found 9/6C$ 544
Sat 12/911:02 p.m.
PDX
-
YWG
1 stop10h 50m
Multiple Airlines
Sat 19/97:20 a.m.
YWG
-
PDX
2 stops9h 31m
Multiple Airlines
Deal found 9/6C$ 548
Sat 12/92:30 p.m.
PDX
-
YWG
2 stops16h 50m
WestJet
Sun 20/910:30 p.m.
YWG
-
PDX
2 stops17h 20m
WestJet
Deal found 9/6C$ 549
Fri 11/911:39 a.m.
PDX
-
YWG
1 stop9h 48m
Delta
Fri 18/95:44 p.m.
YWG
-
PDX
1 stop7h 23m
Delta
Deal found 9/6C$ 555

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 11 June 2026.

Round-trip from

C$ 474

One-way from

C$ 259

Popular in

February

Cheapest in

November

Average price

C$ 693
WestJet
  • WestJet
  • 13/9-21/9
  • 2 total stops
  • 11h 20m total
  • Portland to Winnipeg
Search Deals
Air Canada
  • Air Canada
  • 7/9
  • 1 total stop
  • 15h 25m total
  • Portland to Winnipeg
Search Deals
Highest demand for flights based on searches. 21% potential increase in price (C$ 250 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 72 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 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 11 June 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

Tue 8/9

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

1 stop5h 40m

Winnipeg

Wed 9/9

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

1 stop5h 40m

C$ 534

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$ 555

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 16/8

2:30 p.m.-11:40 p.m.

1 stop7h 10m

Winnipeg

Sun 23/8

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

1 stop5h 40m

C$ 601

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 1/8

10:40 p.m.-11:52 a.m.

1 stop11h 12m

Winnipeg

Tue 11/8

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

2 stops9h 31m

C$ 620

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 8/9

11:02 p.m.-11:52 a.m.

1 stop10h 50m

Winnipeg

Wed 9/9

2:00 p.m.-10:52 p.m.

1 stop10h 52m

C$ 627

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 9/7

3:00 p.m.-11:29 p.m.

1 stop6h 29m

Winnipeg

Mon 13/7

3:59 p.m.-11:18 p.m.

1 stop9h 19m

C$ 627

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 12/11

10:00 a.m.-6:09 p.m.

1 stop6h 09m

Winnipeg

Mon 16/11

5:40 a.m.-9:26 a.m.

1 stop5h 46m

C$ 636
Quickest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 10/7

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

1 stop5h 17m

Winnipeg

Sun 12/7

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

1 stop5h 46m

C$ 748

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 1/8

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

1 stop8h 25m

Winnipeg

Mon 10/8

7:00 a.m.-4:54 p.m.

2 stops11h 54m

C$ 771

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 11/9

8:40 a.m.-10:33 p.m.

2 stops11h 53m

Winnipeg

Sat 12/9

7:00 a.m.-3:05 p.m.

2 stops10h 05m

C$ 794

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/6

Showing 1-10 of 12 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 is the cheapest month to book a flight from Portland to Winnipeg?

Currently, November is the cheapest month in which you can book a flight from Portland to Winnipeg (average of C$ 344). Flying from Portland to Winnipeg in February is currently the most expensive (average of C$ 1,224). 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 Portland to Winnipeg?

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 5h 40m. WestJet provides one of the quickest options available for as low as C$ 534. 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.

  • 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.

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

    Currently, November is the cheapest month in which you can book a flight from Portland to Winnipeg (average of C$ 344). Flying from Portland to Winnipeg in February is currently the most expensive (average of C$ 1,224). 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.

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

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.

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.