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$123+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Portland are usually found in August or July, booked 56 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 July 3, 2025.

Round-trip from

$217
(Air Canada)

One-way from

$123
(SmartFares)

Popular in

June

Cheapest in

August

Average price

$265
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. 6% potential increase in price ($21 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 July 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 July 3, 2025.

This Air Canada deal was found by Cheapflights users on 7/1. 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 7/166:25 pmYWG - PDX
1 stop6h 36mAir Canada
Wed 7/236:15 amPDX - YWG
1 stop6h 30mAir Canada
Deal found 7/1$217
This United Airlines deal was found by Cheapflights users on 7/3. 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 12/188:30 amYWG - PDX
1 stop6h 45mUnited Airlines
Thu 1/19:10 amPDX - YWG
1 stop9h 38mUnited Airlines
Deal found 7/3$306
This Delta deal was found by Cheapflights users on 7/2. 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 12/1812:40 pmYWG - PDX
1 stop9h 45mDelta
Thu 1/11:45 pmPDX - YWG
2 stops7h 47mDelta
Deal found 7/2$328
This Mytrip deal was found by Cheapflights users on 7/1. 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.
Wed 7/163:15 pmYWG - PDX
2 stops20h 03mMultiple Airlines
Wed 7/233:10 pmPDX - YWG
3 stops24h 16mMultiple Airlines
Deal found 7/1$437
This FlightHub deal was found by Cheapflights users on 7/1. 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.
Wed 7/163:00 pmYWG - PDX
2 stops11h 28mWestJet
Tue 7/2212:40 amPDX - YWG
2 stops16h 44mWestJet
Deal found 7/1$497

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 July 3, 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

Wed 7/16

6:25 pm-11:01 pm

1 stop6h 36m

Portland

Wed 7/23

6:15 am-2:45 pm

1 stop6h 30m

$217

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 12/18

8:30 am-1:15 pm

1 stop6h 45m

Portland

Thu 1/1

9:10 am-8:48 pm

1 stop9h 38m

$306

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 12/18

12:40 pm-8:25 pm

1 stop9h 45m

Portland

Thu 1/1

1:45 pm-11:32 pm

2 stops7h 47m

$328

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 7/16

3:15 pm-9:18 am

2 stops20h 03m

Portland

Wed 7/23

3:10 pm-5:26 pm

3 stops24h 16m

$437

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 7/16

3:00 pm-12:28 am

2 stops11h 28m

Portland

Tue 7/22

12:40 am-7:24 pm

2 stops16h 44m

$497

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 7/29

8:30 am-1:04 pm

1 stop6h 34m

$123

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 8/6

5:20 am-9:30 am

1 stop6h 10m

$133

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 8/4

7:00 am-6:45 pm

1 stop13h 45m

$149

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 8/8

8:30 am-11:58 am

3 stops29h 28m

$156

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 8/8

9:00 am-11:59 pm

2 stops16h 59m

$296

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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 June 27, 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 $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 July 3, 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.

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 July 3, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and WestJet 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.
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,861 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,917 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,681 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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?

    Air Canada, at $217, was found to be the cheapest airline from Winnipeg to Portland.Alternate airlines to your destination round-trip include United Airlines and Delta. These flights start at 33% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Winnipeg to Portland one-way?

    One-way options have recently been found by users for as low as $123 on WestJet. Other airlines that offer cheap prices include Air Canada from $133 and United Airlines from $149 one-way.

  • 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
Seaside
Vancouver
Beaverton
Clackamas
Lincoln City
McMinnville
Lake Oswego
Hillsboro
Astoria
Long Beach
Cannon Beach
Tigard
Longview
Hood River
Depoe Bay
Woodburn
Stevenson
Pacific City
Troutdale
Gresham

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