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$139+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
aug. 19 — aug. 261
tir. 8/19
tir. 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Portland are usually found in August or July, booked 57 days in advance, depart on a Tuesday or Monday and return on a Friday

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 august 14, 2025.

Round-trip from

$290
(Kiwi.com)

One-way from

$139
(Air Canada)

Popular in

June

Cheapest in

August

Average price

$226
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. 7% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 august 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 9/118:30 amYWG - PDX
2 stops13h 55mMultiple Airlines
lør. 9/131:45 pmPDX - YWG
1 stop8h 45mMultiple Airlines
Deal found 8/13$290
This Trip.com deal was found by Cheapflights users on 8/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 9/118:30 amYWG - PDX
1 stop6h 34mWestJet
lør. 9/131:45 pmPDX - YWG
1 stop7h 25mWestJet
Deal found 8/13$310
This United Airlines deal was found by Cheapflights users on 8/13. 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.
tor. 9/114:25 pmYWG - PDX
2 stops18h 26mUnited Airlines
lør. 9/135:00 amPDX - YWG
2 stops15h 33mUnited Airlines
Deal found 8/13$316
This Air Canada deal was found by Cheapflights users on 8/14. 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.
tor. 12/1810:45 amYWG - PDX
1 stop6h 00mAir Canada
tor. 1/19:50 amPDX - YWG
1 stop6h 19mAir Canada
Deal found 8/14$330
This Air Canada deal was found by Cheapflights users on 8/12. 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.
tor. 8/215:20 amYWG - PDX
1 stop6h 10mAir Canada
man. 8/253:25 pmPDX - YWG
1 stop6h 10mAir Canada
Deal found 8/12$466
This WestJet deal was found by Cheapflights users on 8/12. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 8/218:30 amYWG - PDX
2 stops8h 08mWestJet
man. 8/255:30 amPDX - YWG
2 stops13h 56mWestJet
Deal found 8/12$559

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 august 14, 2025.
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

tor. 9/11

8:30 am-8:25 pm

2 stops13h 55m

Portland

lør. 9/13

1:45 pm-12:30 am

1 stop8h 45m

$290

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

tor. 9/11

8:30 am-1:04 pm

1 stop6h 34m

Portland

lør. 9/13

1:45 pm-11:10 pm

1 stop7h 25m

$310

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

tor. 9/11

4:25 pm-8:51 am

2 stops18h 26m

Portland

lør. 9/13

5:00 am-10:33 pm

2 stops15h 33m

$316

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

tor. 12/18

10:45 am-2:45 pm

1 stop6h 00m

Portland

tor. 1/1

3:15 pm-1:09 am

1 stop7h 54m

$330

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

man. 9/1

7:15 pm-11:01 pm

1 stop5h 46m

$139

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

man. 9/1

6:15 pm-12:48 pm

2 stops20h 33m

$165

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

tor. 9/18

5:20 am-9:21 am

1 stop6h 01m

$175

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

tor. 9/18

6:30 am-8:25 pm

2 stops15h 55m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

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 August 8, 2025.

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 56 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, November is the cheapest month in which you can book a flight from Winnipeg to Portland (average of $277). Flying from Winnipeg to Portland in March is currently the most expensive (average of $369). 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 YWG to PDX?

Find hourly flight availability from Winnipeg to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated august 14, 2025.

A simple way to save on the total cost of your ticket is to fly from Winnipeg to Portland at noon. If you’re flexible enough to do this you can expect to save up to 3% on your trip compared to booking a flight in the morning.

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.

  • 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, November is the cheapest month in which you can book a flight from Winnipeg to Portland (average of $277). Flying from Winnipeg to Portland in March is currently the most expensive (average of $369). 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
Beaverton
Clackamas
McMinnville
Lake Oswego
Hillsboro
Lincoln City
Cannon Beach
Long Beach
Longview
Tigard
Depoe Bay
Stevenson
Woodburn
Wilsonville
Pacific City
Troutdale
Tillamook
Gresham

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