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$127+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Portland are usually found in July or August, booked 27 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 September 15, 2025.

Round-trip from

$236
(Air Canada)

One-way from

$127
(Air Canada)

Popular in

June

Cheapest in

July

Average price

$365
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. 4% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 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 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 September 15, 2025.

This Air Canada deal was found by Cheapflights users on 9/13. 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.
Tue 10/77:10 pmYWG - PDX
1 stop5h 51mAir Canada
Tue 10/149:55 amPDX - YWG
1 stop14h 07mAir Canada
Deal found 9/13$236
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/712:20 pmYWG - PDX
1 stop10h 06mDelta
Tue 10/147:59 pmPDX - YWG
2 stops13h 31mDelta
Deal found 9/13$241
This Air Canada deal was found by Cheapflights users on 9/14. 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.
Fri 10/247:10 pmYWG - PDX
1 stop5h 51mAir Canada
Mon 10/273:15 pmPDX - YWG
1 stop7h 54mAir Canada
Deal found 9/14$243
This United deal was found by Cheapflights users on 9/14. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/244:25 pmYWG - PDX
2 stops10h 03mMultiple Airlines
Mon 10/273:15 pmPDX - YWG
1 stop7h 54mMultiple Airlines
Deal found 9/14$290
This Air Canada deal was found by Cheapflights users on 9/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/410:45 amYWG - PDX
1 stop6h 00mAir Canada
Fri 11/73:15 pmPDX - YWG
1 stop7h 54mAir Canada
Deal found 9/15$300
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/62:20 pmYWG - PDX
2 stops21h 18mUnited Airlines
Sat 11/811:59 pmPDX - YWG
1 stop9h 58mUnited Airlines
Deal found 9/15$317
This Air Canada deal was found by Cheapflights users on 9/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/310:45 amYWG - PDX
1 stop9h 45mAir Canada
Tue 11/113:15 pmPDX - YWG
1 stop7h 54mAir Canada
Deal found 9/15$318
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 11/45:40 pmYWG - PDX
2 stops16h 56mDelta
Sat 11/81:55 pmPDX - YWG
1 stop7h 32mDelta
Deal found 9/15$321
This Air Canada deal was found by Cheapflights users on 9/14. 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.
Wed 12/178:00 amYWG - PDX
2 stops12h 30mAir Canada
Wed 12/319:50 amPDX - YWG
1 stop6h 19mAir Canada
Deal found 9/14$329
This Air Canada deal was found by Cheapflights users on 9/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/38:00 amYWG - PDX
2 stops12h 30mAir Canada
Sun 11/93:15 pmPDX - YWG
1 stop7h 54mAir Canada
Deal found 9/15$331

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 September 15, 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

Tue 10/7

12:20 pm-8:26 pm

1 stop10h 06m

Portland

Tue 10/14

7:59 pm-11:30 am

2 stops13h 31m

$241

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 10/24

7:10 pm-11:01 pm

1 stop5h 51m

Portland

Mon 10/27

3:15 pm-1:09 am

1 stop7h 54m

$243

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 10/24

4:25 pm-12:28 am

2 stops10h 03m

Portland

Mon 10/27

3:15 pm-1:09 am

1 stop7h 54m

$290

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 11/5

10:45 am-2:45 pm

1 stop6h 00m

Portland

Tue 11/11

3:15 pm-1:09 am

1 stop7h 54m

$300

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 11/5

10:45 am-2:45 pm

1 stop6h 00m

Portland

Thu 11/6

3:15 pm-1:09 am

1 stop7h 54m

$300

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 11/4

10:45 am-2:45 pm

1 stop6h 00m

Portland

Wed 11/12

3:15 pm-1:09 am

1 stop7h 54m

$300

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 3/4

8:00 am-2:45 pm

2 stops8h 45m

Portland

Thu 3/5

3:15 pm-1:09 am

1 stop7h 54m

$311

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 11/6

2:20 pm-9:38 am

2 stops21h 18m

Portland

Mon 11/10

11:59 pm-11:57 am

1 stop9h 58m

$317

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 11/6

2:20 pm-9:38 am

2 stops21h 18m

Portland

Sat 11/8

11:59 pm-11:57 am

1 stop9h 58m

$317

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 3/4

2:20 pm-9:40 am

2 stops21h 20m

Portland

Thu 3/5

3:41 pm-11:39 am

2 stops17h 58m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 19 results
1
2

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 September 12, 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 27 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 $368). 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 September 15, 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.

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 September 15, 2025.
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
10,000 reviews

Food

6.3

Overall

7.1

Boarding

7.3

Crew

7.8

Comfort

7.1

Entertainment

6.8

Reviews

1 / 20
8.0
Excellent

Graeme,Sep 2025

YWG - YVR

Why not start boarding from the higher seat numbers? Easier movement for everyone. Easier to put baggage in over head lockers. Unable to get a coffee due to air turbulence, but not offered the chance to have a coffee once it had ceased.
Air Canada
7.1
Good
10,000 reviews
Air Canada
7.1
Good
10,000 reviews

Food

6.3

Overall

7.1

Boarding

7.3

Crew

7.8

Comfort

7.1

Entertainment

6.8

Reviews

1 / 20
8.0
Excellent

Graeme,Sep 2025

YWG - YVR

Why not start boarding from the higher seat numbers? Easier movement for everyone. Easier to put baggage in over head lockers. Unable to get a coffee due to air turbulence, but not offered the chance to have a coffee once it had ceased.

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 Delta and Air Canada fly from Winnipeg to Portland in about 5h 51m. The time it takes to get you to your destination can typically vary by up to 4h 15m. 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 36% 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, 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 $368). 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
Cannon Beach
Long Beach
Longview
Lincoln City
Tigard
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Troutdale
Gresham
Silverton

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$214Average$330FlexibilityNo cancel feeOn-time67%

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