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$216+ Cheap flights from Portland (PDX) to Winnipeg (YWG)

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Winnipeg are usually found in February or April, booked 27 days in advance, depart on a Friday or Monday and return on a Tuesday

Cheap 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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$417
(Air Canada)

One-way from

$216
(Kiwi.com)

Popular in

May

Cheapest in

February

Average price

$276
Provider with most accurate pricing for Portland-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Portland-Winnipeg flights.
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From Portland to Winnipeg
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One-way flight from Portland to Winnipeg
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Portland to Winnipeg

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 September 29, 2025.

This Air Canada deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/133:15 pmPDX - YWG
1 stop7h 54mAir Canada
Thu 11/2010:45 amYWG - PDX
1 stop6h 00mAir Canada
Deal found 9/29$417
This Air Canada deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/283:15 pmPDX - YWG
1 stop7h 54mAir Canada
Sat 12/68:00 amYWG - PDX
2 stops8h 45mAir Canada
Deal found 9/27$422
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/512:40 amPDX - YWG
1 stop8h 50mDelta
Sun 11/912:38 pmYWG - PDX
1 stop10h 09mDelta
Deal found 9/28$431
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/61:21 pmPDX - YWG
2 stops33h 20mMultiple Airlines
Sun 11/94:55 pmYWG - PDX
1 stop9h 43mMultiple Airlines
Deal found 9/27$432
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/287:59 pmPDX - YWG
2 stops13h 49mDelta
Sat 12/612:35 pmYWG - PDX
2 stops12h 02mDelta
Deal found 9/27$439
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/286:00 amPDX - YWG
1 stop6h 26mDelta
Sun 12/712:35 pmYWG - PDX
2 stops13h 40mDelta
Deal found 9/29$441
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:05 amPDX - YWG
1 stop30h 02mMultiple Airlines
Thu 11/206:15 amYWG - PDX
2 stops12h 20mMultiple Airlines
Deal found 9/29$443

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 2,558,603 searches. Data last updated September 29, 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

Fri 11/28

3:15 pm-1:09 am

1 stop7h 54m

Winnipeg

Sat 12/6

10:45 am-2:45 pm

1 stop6h 00m

$417

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 1/16

3:15 pm-1:09 am

1 stop7h 54m

Winnipeg

Mon 1/19

10:45 am-2:45 pm

1 stop6h 00m

$417

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 3/10

3:15 pm-1:09 am

1 stop7h 54m

Winnipeg

Wed 3/11

8:00 am-2:45 pm

2 stops8h 45m

$422

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 11/6

12:06 pm-11:27 pm

1 stop9h 21m

Winnipeg

Sun 11/9

12:38 pm-8:47 pm

1 stop10h 09m

$431

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 10/14

5:55 pm-9:25 pm

3 stops25h 30m

$216

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 10/18

12:40 am-11:30 am

1 stop8h 50m

$234

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 10/14

5:00 am-1:09 pm

1 stop6h 09m

$234

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 10/14

7:59 pm-11:30 am

2 stops13h 31m

$239

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 10/19

3:25 pm-2:02 am

1 stop8h 37m

$248

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 10/19

11:59 pm-12:30 am

3 stops46h 31m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 11 results
1
2

Compare providers for flights from Portland to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Winnipeg in September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Portland-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

How far ahead should I book a flight from Portland to Winnipeg?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Winnipeg. Price data was last updated on September 26, 2025.

Booking 27 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Winnipeg. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, August is the cheapest month in which you can book a flight from Portland to Winnipeg (average of $358). Flying from Portland to Winnipeg in December is currently the most expensive (average of $501). 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.

What is the cheapest time of day to fly from PDX to YWG?

Find hourly flight availability from Portland to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 29, 2025.

A simple way to save on the total cost of your ticket is to fly from Portland to Winnipeg in the afternoon. If you’re flexible enough to do this you can expect to save up to 21% on your trip compared to booking a flight in the evening.

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 September 29, 2025.
Read reviews from past customers who have flown Delta, WestJet, and Air Canada from Portland to Winnipeg. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
3,110 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
10,000 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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?

    Departing from Portland to Winnipeg will take you 7h 54m. There are 1208 mi between Portland and Winnipeg.

  • What are the cheapest airlines flying from Portland to Winnipeg round-trip?

    Our cheapest airline available from Portland to Winnipeg is WestJet. Our recent data shows that you can find tickets from as low as $135 on this airline. Additional options worth looking into are Delta and Air Canada, starting at $143 and $183 round-trip. You may be able to fly from Portland to Winnipeg for 58% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Portland to Winnipeg one-way?

    The cheapest airlines for a one-way flight from Portland to Winnipeg are Delta ($234), United Airlines ($234), and Air Canada ($248).

  • 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, August is the cheapest month in which you can book a flight from Portland to Winnipeg (average of $358). Flying from Portland to Winnipeg in December is currently the most expensive (average of $501). 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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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

Top 3 airlines flying from Portland to Winnipeg

Discover the top 3 airlines 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 2,558,603 searches. Data last updated September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$135Average$319FlexibilityNo cancel feeOn-time60%
DeltaCheapest$143Average$484FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$183Average$332FlexibilityNo cancel feeOn-time67%

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