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$156+ Cheap flights from Winnipeg (YWG) to Portland (PDX)

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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap flight deals from Winnipeg to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Portland (PDX). 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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$243
(Air Canada)

One-way from

$156
(United Airlines)

Popular in

January

Cheapest in

August

Average price

$789
Provider with most accurate pricing for Winnipeg-Portland flight deals.
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Provider most trusted by Cheapflights users for Winnipeg-Portland flights.
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From Winnipeg to Portland
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One-way flight from Winnipeg to Portland
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Highest demand for flights based on searches. 20% potential increase in price ($99 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($38 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Winnipeg to Portland

Cheapest flights from Winnipeg to Portland
Explore the most affordable flight options available from Winnipeg to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.

This Air Canada deal was found by Cheapflights users on 1/13. 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.
Sun 3/19:50 pm
YWG
-
PDX
1 stop13h 25m
Air Canada
Sat 3/79:50 am
PDX
-
YWG
1 stop6h 29m
Air Canada
Deal found 1/13$243
This United Airlines deal was found by Cheapflights users on 1/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/282:20 pm
YWG
-
PDX
1 stop10h 36m
United Airlines
Wed 3/47:57 pm
PDX
-
YWG
2 stops14h 00m
United Airlines
Deal found 1/13$246
This Air Canada deal was found by Cheapflights users on 1/13. 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 3/269:15 pm
YWG
-
PDX
2 stops14h 00m
Air Canada
Sun 3/293:15 pm
PDX
-
YWG
1 stop7h 59m
Air Canada
Deal found 1/13$266
This Air Canada deal was found by Cheapflights users on 1/12. 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.
Sat 2/286:00 am
YWG
-
PDX
1 stop14h 30m
Air Canada
Wed 3/43:15 pm
PDX
-
YWG
1 stop7h 59m
Air Canada
Deal found 1/12$272
This Delta deal was found by Cheapflights users on 1/15. 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.
Thu 3/2612:50 pm
YWG
-
PDX
1 stop10h 22m
Delta
Sun 3/297:43 pm
PDX
-
YWG
2 stops14h 17m
Delta
Deal found 1/15$353
This Air Canada deal was found by Cheapflights users on 1/14. 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.
Sat 2/288:00 am
YWG
-
PDX
2 stops12h 30m
Air Canada
Thu 3/59:50 am
PDX
-
YWG
2 stops9h 38m
Air Canada
Deal found 1/14$437
This Air Canada deal was found by Cheapflights users on 1/14. 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.
Sun 2/89:50 pm
YWG
-
PDX
1 stop13h 25m
Air Canada
Fri 2/137:05 pm
PDX
-
YWG
1 stop15h 54m
Air Canada
Deal found 1/14$468

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Portland 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 January 15, 2026.
Use the filters below to find and compare flights from Winnipeg to Portland that are best for you.

Fly from

Winnipeg

Fly to

Portland

Route

Depart

Return

Price

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 2/28

2:20 pm-10:56 pm

1 stop10h 36m

Portland

Wed 3/4

11:59 pm-11:57 am

1 stop9h 58m

$246

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 3/26

9:15 pm-9:15 am

2 stops14h 00m

Portland

Sun 3/29

3:15 pm-1:14 am

1 stop7h 59m

$266

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 3/1

6:00 am-6:30 pm

1 stop14h 30m

Portland

Sat 3/7

9:50 am-11:43 pm

2 stops11h 53m

$267

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 2/28

9:50 pm-9:15 am

1 stop13h 25m

Portland

Thu 3/5

3:15 pm-1:14 am

1 stop7h 59m

$272

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 2/28

6:00 am-6:30 pm

1 stop14h 30m

Portland

Wed 3/4

3:15 pm-1:14 am

1 stop7h 59m

$272

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 3/26

12:50 pm-9:12 pm

1 stop10h 22m

Portland

Sun 3/29

7:43 pm-12:00 pm

2 stops14h 17m

$353

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 2/27

2:20 pm-9:42 am

2 stops21h 22m

$156

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 2/27

11:53 am-8:30 pm

1 stop10h 37m

$158

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 2/27

9:00 am-10:46 am

3 stops27h 46m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

Compare providers for flights from Winnipeg to Portland

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 Winnipeg to Portland in January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice 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 Winnipeg-Portland flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Winnipeg-Portland flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Winnipeg-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-Portland flights, Cheapflights users trust eDreams the most. eDreams 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 Winnipeg-Portland 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 Winnipeg to Portland

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

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

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Portland (average of $140). Flying from Winnipeg to Portland in January is currently the most expensive (average of $504). 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 Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated January 15, 2026.
Peruse reviews from past customers who have flown with Air Canada from Winnipeg to Portland to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,624 reviews

Crew

7.8

Entertainment

6.8

Food

6.3

Overall

7.1

Boarding

7.3

Comfort

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍
Air Canada
7.1
Good
10,624 reviews
Air Canada
7.1
Good
10,624 reviews

Crew

7.8

Entertainment

6.8

Food

6.3

Overall

7.1

Boarding

7.3

Comfort

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Portland. 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 Winnipeg to Portland?

    Airlines like United Airlines and Air Canada fly from Winnipeg to Portland in about 10h 36m. The time it takes to get you to your destination can typically vary by up to 3h 24m. Winnipeg and Portland are separated by a distance of 1208 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Air Canada, at $169, was found to be the cheapest airline from Winnipeg to Portland.. This flight start at 55% lower than the current average price 3 months from now.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Portland 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 Winnipeg to Portland?

    Currently, August is the cheapest month in which you can book a flight from Winnipeg to Portland (average of $140). Flying from Winnipeg to Portland in January is currently the most expensive (average of $504). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Clackamas
Lincoln City
Longview
Lake Oswego
Beaverton
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Tillamook
Pacific City
Gresham

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Winnipeg to Portland

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Medford flights

Top airline flying from Winnipeg to Portland

Discover the top airline that operate flights from Winnipeg to Portland. 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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$169Average$330FlexibilityNo cancel feeOn-time67%

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