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$128+ 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 6/14. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Portland are usually found in August or July, booked 87 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 April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$228
(Trip.com)

One-way from

$128
(Trip.com)

Popular in

June

Cheapest in

August

Average price

$326
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. 4% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 30, 2025.

This Trip.com deal was found by Cheapflights users on 4/29. 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.
Fri 7/116:30 amYWG - PDX
1 stop8h 22mWestJet
Sun 7/131:45 pmPDX - YWG
1 stop5h 46mWestJet
Deal found 4/29$228
This Delta deal was found by Cheapflights users on 4/29. 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.
Fri 6/1312:26 pmYWG - PDX
1 stop9h 57mDelta
Fri 6/208:29 pmPDX - YWG
2 stops13h 07mDelta
Deal found 4/29$304
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Mon 5/124:25 pmYWG - PDX
1 stop6h 41mUnited Airlines
Fri 5/167:19 pmPDX - YWG
1 stop15h 50mUnited Airlines
Deal found 4/29$328
This Air Canada deal was found by Cheapflights users on 4/29. 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 12/188:30 amYWG - PDX
2 stops8h 14mAir Canada
Thu 1/110:10 amPDX - YWG
2 stops8h 55mAir Canada
Deal found 4/29$379
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/134:30 pmYWG - PDX
2 stops22h 22mMultiple Airlines
Fri 6/206:39 pmPDX - YWG
3 stops27h 02mMultiple Airlines
Deal found 4/29$455

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 April 30, 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

Fri 7/11

6:30 am-12:52 pm

1 stop8h 22m

Portland

Sun 7/13

1:45 pm-9:31 pm

1 stop5h 46m

$228

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 6/13

12:26 pm-8:23 pm

1 stop9h 57m

Portland

Fri 6/20

8:29 pm-11:36 am

2 stops13h 07m

$304

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 6/13

5:20 am-9:20 am

1 stop6h 00m

Portland

Fri 6/20

3:25 pm-11:34 pm

1 stop6h 09m

$410

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 6/13

4:30 pm-12:52 pm

2 stops22h 22m

Portland

Fri 6/20

6:39 pm-11:41 pm

3 stops27h 02m

$455

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 6/14

8:30 am-12:52 pm

1 stop6h 22m

$128

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 6/14

2:20 pm-7:42 am

2 stops19h 22m

$169

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 6/14

8:30 am-8:19 pm

3 stops13h 49m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice 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 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

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 April 25, 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 85 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 April 30, 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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

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 April 30, 2025.
Delta
8.0
Very good
7,929 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,929 reviews
Delta
8.0
Very good
7,929 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,929 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,826 reviews
Delta
8.0
Very good
7,929 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Canada
7.0
Good
9,244 reviews
Delta
8.0
Very good
7,929 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • What are the cheapest airlines flying from Winnipeg to Portland round-trip?

    WestJet, at $228, was found to be the cheapest airline from Winnipeg to Portland.Alternate airlines to your destination round-trip include Delta and United Airlines. These flights start at 29% 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 Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Beaverton
Lincoln City
Seaside
Clackamas
Vancouver
McMinnville
Lake Oswego
Hillsboro
Gresham
Astoria
Long Beach
Cannon Beach
Tigard
Hood River
Woodburn
Depoe Bay
Pacific City
Stevenson
Troutdale
Longview

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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$203Average$295FlexibilityNo cancel feeOn-time60%

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