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$153+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Jun 16 — Jun 231
Tue 6/16
Tue 6/23
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 May 17, 2026.

This Trip.com deal was found by Cheapflights users on 5/17. 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.
Mon 8/1710:10 am
YWG
-
PDX
1 stop5h 40m
WestJet
Sun 8/232:30 pm
PDX
-
YWG
1 stop7h 10m
WestJet
Deal found 5/17$232
This oojo deal was found by Cheapflights users on 5/13. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:10 am
YWG
-
PDX
1 stop5h 40m
WestJet
Sat 8/222:30 pm
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 5/13$233
This oojo deal was found by Cheapflights users on 5/13. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:00 am
YWG
-
PDX
2 stops8h 50m
WestJet
Wed 7/152:30 pm
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 5/13$245
This Air Canada deal was found by Cheapflights users on 5/12. 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.
Tue 7/75:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Tue 7/217:45 pm
PDX
-
YWG
1 stop5h 17m
Air Canada
Deal found 5/12$263
This Air Canada deal was found by Cheapflights users on 5/12. 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 6/275:30 am
YWG
-
PDX
1 stop6h 01m
Air Canada
Mon 7/137:45 pm
PDX
-
YWG
1 stop5h 17m
Air Canada
Deal found 5/12$277
This oojo deal was found by Cheapflights users on 5/16. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:00 am
YWG
-
PDX
2 stops8h 50m
WestJet
Tue 6/232:30 pm
PDX
-
YWG
2 stops19h 30m
WestJet
Deal found 5/16$278
This Air Canada deal was found by Cheapflights users on 5/16. 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.
Wed 6/245:30 am
YWG
-
PDX
1 stop6h 01m
Air Canada
Wed 7/157:45 pm
PDX
-
YWG
1 stop5h 17m
Air Canada
Deal found 5/16$279

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 May 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$232
(Trip.com)

One-way from

$153
(Trip.com)

Popular in

March

Cheapest in

August

Average price

$409
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
One-way flight from Winnipeg to Portland
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($109 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 17, 2026.
Use the filters below to find and compare flights from Winnipeg to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 8/17

4:15 pm-1:50 pm

2 stops23h 35m

Portland

Sat 8/22

2:30 pm-12:00 pm

2 stops19h 30m

$263

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 6/24

7:00 am-1:50 pm

2 stops8h 50m

Portland

Wed 7/15

2:30 pm-9:20 am

2 stops16h 50m

$270
Quickest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 6/24

5:30 am-9:31 am

1 stop6h 01m

Portland

Wed 7/15

7:45 pm-3:02 am

1 stop5h 17m

$279

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 9/19

5:45 am-9:31 am

1 stop5h 46m

Portland

Wed 9/23

10:10 am-5:47 pm

1 stop5h 37m

$284

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 9/22

7:00 am-11:10 pm

1 stop18h 10m

Portland

Wed 9/23

7:00 am-10:33 pm

2 stops13h 33m

$289

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 9/19

7:00 am-11:10 pm

1 stop18h 10m

Portland

Wed 9/23

5:00 am-10:33 pm

2 stops15h 33m

$289

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 9/16

7:00 am-9:05 pm

2 stops16h 05m

Portland

Tue 9/22

5:00 am-10:33 pm

2 stops15h 33m

$289

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 9/17

7:00 am-11:10 pm

1 stop18h 10m

Portland

Mon 9/21

11:02 pm-11:52 am

1 stop10h 50m

$289

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 8/17

5:40 am-9:31 am

1 stop5h 51m

Portland

Sat 8/22

3:30 pm-2:57 am

1 stop9h 27m

$308
Cheapest one-way
Quickest one-way

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 6/14

10:10 am-1:50 pm

1 stop5h 40m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

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 May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice 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 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 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 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 $261). Flying from Winnipeg to Portland in March is currently the most expensive (average of $572). 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.

How much does it cost to fly round-trip from Winnipeg to Portland?

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 May 17, 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
11,055 reviews

Crew

7.8

Overall

7.1

Food

6.3

Entertainment

6.8

Boarding

7.3

Comfort

7.1

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.
Air Canada
7.1
Good
11,055 reviews
Air Canada
7.1
Good
11,055 reviews

Crew

7.8

Overall

7.1

Food

6.3

Entertainment

6.8

Boarding

7.3

Comfort

7.1

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.

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 WestJet, Air Canada, and United Airlines fly from Winnipeg to Portland in about 6h 01m. The time it takes to get you to your destination can typically vary by up to 17h 34m. 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 $214, was found to be the cheapest airline from Winnipeg to Portland.. This flight start at 47% 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 $261). Flying from Winnipeg to Portland in March is currently the most expensive (average of $572). 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
Beaverton
Seaside
Vancouver
Lincoln City
Longview
Lake Oswego
Hillsboro
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
Gresham

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 May 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$214Average$384FlexibilityNo cancel feeOn-time67%

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