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$370+ Cheap flights from Winnipeg (YWG) to Portland (PDX)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap 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 20, 2026.

This Air Canada deal was found by Cheapflights users on 1/19. 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 5/105:45 am
YWG
-
PDX
1 stop5h 45m
Air Canada
Wed 5/133:25 pm
PDX
-
YWG
1 stop6h 14m
Air Canada
Deal found 1/19$370
This Air Canada deal was found by Cheapflights users on 1/20. 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 3/810:40 am
YWG
-
PDX
1 stop6h 00m
Air Canada
Wed 3/113:15 pm
PDX
-
YWG
1 stop7h 59m
Air Canada
Deal found 1/20$377
This United Airlines deal was found by Cheapflights users on 1/19. 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 1/19$382
This Air Canada deal was found by Cheapflights users on 1/20. 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 3/2610:10 pm
YWG
-
PDX
1 stop13h 05m
Air Canada
Sun 3/293:15 pm
PDX
-
YWG
1 stop7h 59m
Air Canada
Deal found 1/20$388
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Sun 3/82:20 pm
YWG
-
PDX
1 stop10h 25m
United Airlines
Wed 3/117:49 pm
PDX
-
YWG
2 stops14h 08m
United Airlines
Deal found 1/20$412
This Trip.com deal was found by Cheapflights users on 1/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/207:00 am
YWG
-
PDX
2 stops8h 20m
WestJet
Mon 6/222:00 pm
PDX
-
YWG
1 stop19h 40m
WestJet
Deal found 1/19$466
This United Airlines deal was found by Cheapflights users on 1/19. 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.
Sun 5/108:45 am
YWG
-
PDX
1 stop16h 09m
United Airlines
Wed 5/135:20 am
PDX
-
YWG
3 stops13h 37m
United Airlines
Deal found 1/19$467
This Air Canada deal was found by Cheapflights users on 1/18. 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
Wed 3/47:05 pm
PDX
-
YWG
2 stops24h 23m
Air Canada
Deal found 1/18$480

Find 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 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Kiwi.com
3 stars

Round-trip from

$339
(United Airlines)

Popular in

January

Cheapest in

August

Average price

$472
Provider with most accurate pricing for Winnipeg-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Portland flights.
Search Deals
From Winnipeg to Portland
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 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 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 20, 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

Sun 5/10

5:45 am-9:30 am

1 stop5h 45m

Portland

Wed 5/13

3:25 pm-11:39 pm

1 stop6h 14m

$370

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 3/8

10:40 am-2:40 pm

1 stop6h 00m

Portland

Wed 3/11

3:15 pm-1:14 am

1 stop7h 59m

$377

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 5/10

8:45 am-10:54 pm

1 stop16h 09m

Portland

Wed 5/13

1:37 pm-11:52 am

2 stops20h 15m

$382

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 6/20

12:40 pm-8:15 pm

1 stop9h 35m

Portland

Mon 6/22

11:39 am-11:27 pm

1 stop9h 48m

$382

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

$382

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 3/26

10:10 pm-9:15 am

1 stop13h 05m

Portland

Sun 3/29

3:15 pm-1:14 am

1 stop7h 59m

$389

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 3/8

2:20 pm-10:45 pm

1 stop10h 25m

Portland

Wed 3/11

7:49 pm-11:57 am

2 stops14h 08m

$412

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

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
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Portland flight deals on Cheapflights vs. FlightHub >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 Kiwi.com the most. Kiwi.com 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

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

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Portland. Price data was last updated on January 16, 2026.

The price you pay for your flight from Winnipeg to Portland may vary depending on when you book. For the best chance of a lower fare, look to book 36 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 $351). 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 20, 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
10,637 reviews

Food

6.3

Boarding

7.3

Entertainment

6.8

Comfort

7.1

Crew

7.8

Overall

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
10,637 reviews
Air Canada
7.1
Good
10,637 reviews

Food

6.3

Boarding

7.3

Entertainment

6.8

Comfort

7.1

Crew

7.8

Overall

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 Air Canada and United Airlines fly from Winnipeg to Portland in about 5h 45m. The time it takes to get you to your destination can typically vary by up to 10h 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 52% 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 $351). 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 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$169Average$341FlexibilityNo cancel feeOn-time67%

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