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Cheap flights from Portland to Winnipeg from C$ 238

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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
28 Feb — 7 Mar1
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 29 January 2026.

Wed 29/42:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Sat 2/53:15 p.m.
YWG
-
PDX
2 stops24h 35m
WestJet
Deal found 28/1C$ 380
Wed 29/42:30 p.m.
PDX
-
YWG
1 stop5h 40m
Multiple Airlines
Sat 2/56:00 a.m.
YWG
-
PDX
2 stops31h 57m
Multiple Airlines
Deal found 28/1C$ 478
Thu 26/211:59 p.m.
PDX
-
YWG
1 stop9h 58m
United Airlines
Thu 5/32:20 p.m.
YWG
-
PDX
2 stops21h 34m
United Airlines
Deal found 27/1C$ 599
Mon 30/34:15 p.m.
PDX
-
YWG
2 stops17h 37m
United Airlines
Tue 31/32:00 p.m.
YWG
-
PDX
2 stops21h 48m
United Airlines
Deal found 26/1C$ 604
Wed 29/41:39 p.m.
PDX
-
YWG
2 stops20h 13m
United Airlines
Sat 2/58:45 a.m.
YWG
-
PDX
2 stops12h 01m
United Airlines
Deal found 28/1C$ 605
Fri 3/73:25 p.m.
PDX
-
YWG
1 stop6h 12m
Air Canada
Sat 11/75:45 a.m.
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 27/1C$ 641
Thu 26/23:15 p.m.
PDX
-
YWG
1 stop7h 59m
Air Canada
Thu 5/310:40 a.m.
YWG
-
PDX
1 stop6h 00m
Air Canada
Deal found 28/1C$ 645
Fri 3/72:00 p.m.
PDX
-
YWG
2 stops7h 10m
WestJet
Sat 11/78:30 a.m.
YWG
-
PDX
1 stop6h 50m
WestJet
Deal found 28/1C$ 660
Wed 18/33:15 p.m.
PDX
-
YWG
1 stop7h 59m
Air Canada
Thu 26/310:10 p.m.
YWG
-
PDX
1 stop13h 05m
Air Canada
Deal found 27/1C$ 667

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 29 January 2026.

Round-trip from

C$ 380

One-way from

C$ 238

Popular in

December

Cheapest in

February

Average price

C$ 515
WestJet
  • WestJet
  • 29/4-2/5
  • 3 total stops
  • 30h 15m total
  • Portland to Winnipeg
Search Deals
12/3
  • 12/3
  • 3 total stops
  • 20h 40m total
  • Portland to Winnipeg
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 134 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 29 January 2026.
Use the filters below to find and compare flights from Portland to Winnipeg that are best for you.

Fly from

Portland

Fly to

Winnipeg

Route

Depart

Return

Price

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 29/4

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

1 stop5h 40m

Winnipeg

Sat 2/5

3:15 p.m.-1:50 p.m.

2 stops24h 35m

C$ 380

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 26/2

11:59 p.m.-11:57 a.m.

1 stop9h 58m

Winnipeg

Thu 5/3

2:20 p.m.-9:54 a.m.

2 stops21h 34m

C$ 599

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 30/3

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

2 stops17h 37m

Winnipeg

Tue 31/3

2:00 p.m.-9:48 a.m.

2 stops21h 48m

C$ 604

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 29/4

1:39 p.m.-11:52 a.m.

2 stops20h 13m

Winnipeg

Sat 2/5

8:45 a.m.-6:46 p.m.

2 stops12h 01m

C$ 605

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 3/7

3:25 p.m.-11:37 p.m.

1 stop6h 12m

Winnipeg

Sat 11/7

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

1 stop5h 46m

C$ 641

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 26/2

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

1 stop7h 59m

Winnipeg

Thu 5/3

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

1 stop6h 00m

C$ 641

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 3/7

2:00 p.m.-11:10 p.m.

2 stops7h 10m

Winnipeg

Sat 11/7

8:30 a.m.-1:20 p.m.

1 stop6h 50m

C$ 660

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 12/3

9:53 a.m.-8:33 a.m.

3 stops20h 40m

C$ 238

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 12/3

11:59 p.m.-11:57 a.m.

1 stop9h 58m

C$ 255

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/1

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, July is the cheapest month in which you can book a flight from Portland to Winnipeg (average of C$ 189). Flying from Portland to Winnipeg in December is currently the most expensive (average of C$ 684). 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.

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 29 January 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
3,253 reviews
Check prices

Overall

7.2

Entertainment

6.1

Food

6.2

Crew

7.9

Boarding

7.4

Comfort

7.0

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
3,253 reviews
WestJet
7.2
Good
3,253 reviews
Check prices

Overall

7.2

Entertainment

6.1

Food

6.2

Crew

7.9

Boarding

7.4

Comfort

7.0

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 5h 40m. WestJet provides one of the quickest options available for as low as C$ 380. 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 48% 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.

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

    Currently, July is the cheapest month in which you can book a flight from Portland to Winnipeg (average of C$ 189). Flying from Portland to Winnipeg in December is currently the most expensive (average of C$ 684). 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
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 29 January 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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