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Cheap flights from Portland to Winnipeg from C$ 182

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 25/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
11 Jan — 18 Jan1
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 December 2025.

Thu 25/1211:55 p.m.PDX - YWG
1 stop10h 02mUnited Airlines
Mon 29/128:40 a.m.YWG - PDX
1 stop14h 27mUnited Airlines
Deal found 9/12C$ 1,113
Thu 25/1212:29 p.m.PDX - YWG
2 stops10h 12mWestJet
Mon 29/126:45 a.m.YWG - PDX
2 stops30h 20mWestJet
Deal found 9/12C$ 1,331
Thu 25/1211:59 p.m.PDX - YWG
3 stops21h 36mAmerican Airlines
Mon 29/126:00 a.m.YWG - PDX
2 stops17h 19mAmerican Airlines
Deal found 9/12C$ 2,151

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 December 2025.

Round-trip from

C$ 510

One-way from

C$ 182

Popular in

December

Cheapest in

February

Average price

C$ 792
Air Canada
  • Air Canada
  • 12/1-15/1
  • 2 total stops
  • 13h 54m total
  • Portland to Winnipeg
Search Deals
25/1
  • 25/1
  • 2 total stops
  • 35h 34m total
  • Portland to Winnipeg
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 143 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 47 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 2025.
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

Mon 12/1

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

1 stop7h 59m

Winnipeg

Thu 15/1

10:45 a.m.-2:40 p.m.

1 stop5h 55m

C$ 510

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 25/1

2:53 p.m.-12:43 a.m.

1 stop7h 50m

Winnipeg

Sun 1/2

2:40 p.m.-10:46 p.m.

2 stops10h 06m

C$ 525

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 12/1

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

1 stop9h 58m

Winnipeg

Thu 15/1

2:20 p.m.-10:32 p.m.

1 stop10h 12m

C$ 531

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 23/1

2:53 p.m.-12:53 a.m.

1 stop8h 00m

Winnipeg

Sun 25/1

4:55 p.m.-11:18 a.m.

2 stops20h 23m

C$ 576

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 25/1

9:50 a.m.-6:09 p.m.

1 stop6h 19m

Winnipeg

Sun 1/2

9:50 p.m.-9:15 a.m.

1 stop13h 25m

C$ 601

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 25/1

11:09 a.m.-12:43 a.m.

2 stops35h 34m

C$ 182

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 4/3

9:48 p.m.-7:45 p.m.

2 stops19h 57m

C$ 219

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 4/3

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

1 stop7h 59m

C$ 254

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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 67% 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$ 387.

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 December 2025.
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
3,195 reviews
Check prices

Comfort

7.1

Crew

7.9

Overall

7.2

Entertainment

6.1

Food

6.2

Boarding

7.4

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
3,195 reviews
WestJet
7.2
Good
3,195 reviews
Check prices

Comfort

7.1

Crew

7.9

Overall

7.2

Entertainment

6.1

Food

6.2

Boarding

7.4

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 7h 59m. Air Canada provides one of the quickest options available for as low as C$ 510. The distance from Portland to Winnipeg is about 1944 km.

  • 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$ 244. WestJet is 47% 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 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 244AverageC$ 297FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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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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