HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$174+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$310
(Air Canada)

One-way from

$174
(Air Canada)

Popular in

June

Cheapest in

August

Average price

$352
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. 1% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 13, 2025.

This Air Canada deal was found by Cheapflights users on 11/12. 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.
Thu 12/1810:45 amYWG - PDX
1 stop9h 45mAir Canada
Thu 1/13:15 pmPDX - YWG
1 stop7h 59mAir Canada
Deal found 11/12$341
This United deal was found by Cheapflights users on 11/12. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/222:20 pmYWG - PDX
2 stops10h 36mMultiple Airlines
Sat 11/297:00 pmPDX - YWG
1 stop15h 59mMultiple Airlines
Deal found 11/12$457
This Air Canada deal was found by Cheapflights users on 11/12. 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 11/228:00 amYWG - PDX
2 stops12h 30mAir Canada
Sat 11/297:00 pmPDX - YWG
1 stop15h 59mAir Canada
Deal found 11/12$478
This FlightHub deal was found by Cheapflights users on 11/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/225:49 pmYWG - PDX
1 stop25h 54mWestJet
Fri 11/2812:35 amPDX - YWG
1 stop21h 01mWestJet
Deal found 11/12$500
This United Airlines deal was found by Cheapflights users on 11/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/182:20 pmYWG - PDX
2 stops21h 41mUnited Airlines
Thu 1/17:30 amPDX - YWG
2 stops26h 27mUnited Airlines
Deal found 11/12$504
This FlightHub deal was found by Cheapflights users on 11/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:49 pmYWG - PDX
1 stop19h 25mWestJet
Sat 11/1512:35 amPDX - YWG
1 stop9h 13mWestJet
Deal found 11/11$654
This Delta deal was found by Cheapflights users on 11/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:38 pmYWG - PDX
1 stop10h 09mDelta
Sat 11/1512:35 amPDX - YWG
1 stop9h 13mDelta
Deal found 11/12$759

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 November 13, 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

Thu 12/18

10:45 am-6:30 pm

1 stop9h 45m

Portland

Thu 1/1

3:15 pm-1:14 am

1 stop7h 59m

$341

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 3/4

10:40 am-2:40 pm

1 stop6h 00m

Portland

Thu 3/5

3:15 pm-1:14 am

1 stop7h 59m

$343

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 3/4

2:20 pm-9:43 am

2 stops21h 23m

Portland

Thu 3/5

1:35 pm-11:39 am

2 stops20h 04m

$349

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 12/18

6:45 am-5:43 pm

2 stops12h 58m

Portland

Thu 1/1

12:29 pm-10:41 pm

2 stops8h 12m

$500

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 12/18

2:20 pm-10:01 am

2 stops21h 41m

Portland

Thu 1/1

7:30 am-11:57 am

2 stops26h 27m

$504

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 3/4

6:35 am-8:32 pm

1 stop15h 57m

Portland

Wed 3/4

12:40 am-11:01 am

1 stop8h 21m

$542

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 12/8

10:45 am-2:40 pm

1 stop5h 55m

$174

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 12/5

5:35 pm-9:34 am

2 stops41h 59m

$185

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 12/5

9:40 pm-9:15 am

1 stop13h 35m

$210

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 12/30

9:00 pm-3:00 pm

3 stops20h 00m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 13 results
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 November.
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 December is currently the most expensive (average of $325). 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 November 13, 2025.

A simple way to save on the total cost of your ticket is to fly from Winnipeg to Portland in the afternoon. If you’re flexible enough to do this you can expect to save up to 40% on your trip compared to booking a flight at noon.

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 November 13, 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
10,448 reviews

Crew

7.8

Comfort

7.1

Entertainment

6.8

Food

6.3

Overall

7.1

Boarding

7.3

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
10,448 reviews
Air Canada
7.1
Good
10,448 reviews

Crew

7.8

Comfort

7.1

Entertainment

6.8

Food

6.3

Overall

7.1

Boarding

7.3

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 Air Canada and United Airlines fly from Winnipeg to Portland in about 9h 45m. The time it takes to get you to your destination can typically vary by up to 11h 38m. 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 39% 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 December is currently the most expensive (average of $325). 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
Lake Oswego
Beaverton
McMinnville
Hillsboro
Cannon Beach
Long Beach
Longview
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Gresham
Troutdale

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.

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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$214Average$330FlexibilityNo cancel feeOn-time67%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.