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$108+ Cheap flights from Oregon to Winnipeg (YWG)

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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Jul 30 — Aug 61
Wed 7/30
Wed 8/6
1 adult, Economy
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Cheap flight deals from Oregon to Winnipeg

Keep the following information in mind while searching for Oregon to Winnipeg flight deals. Data was last updated July 25, 2025.

Round-trip from

$265
(Air Canada)

One-way from

$108
(Air Canada)

Popular in

May

Cheapest in

February

Average price

$320
From Oregon to Winnipeg
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One-way flight from Oregon to Winnipeg
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Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 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 Oregon to Winnipeg

Cheapest flights from Oregon to Winnipeg
Explore the most affordable flight options available from Oregon to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 25, 2025.

This Air Canada deal was found by Cheapflights users on 7/24. 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 8/196:15 amPDX - YWG
1 stop6h 30mAir Canada
Sat 8/236:25 pmYWG - PDX
1 stop6h 36mAir Canada
Deal found 7/24$265
This Delta deal was found by Cheapflights users on 7/24. 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 10/237:55 pmPDX - YWG
2 stops13h 43mDelta
Fri 11/77:30 amYWG - PDX
1 stop13h 38mDelta
Deal found 7/24$401
This Mytrip deal was found by Cheapflights users on 7/24. 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.
Thu 10/238:04 pmPDX - YWG
2 stops19h 36mMultiple Airlines
Fri 11/77:40 amYWG - PDX
2 stops29h 09mMultiple Airlines
Deal found 7/24$455
This WestJet deal was found by Cheapflights users on 7/24. 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.
Tue 8/51:45 pmPDX - YWG
2 stops7h 56mWestJet
Thu 8/146:30 amYWG - PDX
2 stops8h 34mWestJet
Deal found 7/24$510

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon to Winnipeg 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 25, 2025.
Use the filters below to find and compare flights from Oregon to Winnipeg that are best for you.

Fly from

Oregon

Fly to

Winnipeg

Route

Depart

Return

Price

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 8/19

6:15 am-2:45 pm

1 stop6h 30m

Winnipeg

Sat 8/23

6:25 pm-11:01 pm

1 stop6h 36m

$265

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 10/23

7:55 pm-11:38 am

2 stops13h 43m

Winnipeg

Fri 11/7

7:30 am-7:08 pm

1 stop13h 38m

$401

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 10/23

8:04 pm-5:40 pm

2 stops19h 36m

Winnipeg

Fri 11/7

7:40 am-10:49 am

2 stops29h 09m

$455

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 8/5

1:45 pm-11:41 pm

2 stops7h 56m

Winnipeg

Thu 8/14

6:30 am-1:04 pm

2 stops8h 34m

$510

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 8/14

6:15 am-2:45 pm

1 stop6h 30m

$108

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 8/13

12:46 am-11:49 am

1 stop9h 03m

$113

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 9/7

8:04 pm-9:25 pm

3 stops23h 21m

$151

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 8/5

1:45 pm-11:41 pm

2 stops7h 56m

$205

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 8/11

6:43 pm-3:31 pm

2 stops18h 48m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/25

Best time to book a flight from Oregon to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Oregon 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 Oregon to Winnipeg

What is the cheapest month to book a flight from Oregon to Winnipeg?

Currently, August is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of $358). Flying from Oregon to Winnipeg in December is currently the most expensive (average of $497). 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 OR to YWG?

Find hourly flight availability from Oregon to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 25, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Winnipeg as you normally would.

How much does it cost to fly round-trip from Oregon to Winnipeg?

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated July 25, 2025.
Read through reviews of airlines operating flights from Oregon to Winnipeg, such as Delta, United Airlines, and WestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,967 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

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
7,967 reviews
Delta
8.0
Very good
7,967 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

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
8,876 reviews
Delta
8.0
Very good
7,967 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

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
2,963 reviews
Delta
8.0
Very good
7,967 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

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
9,788 reviews
Delta
8.0
Very good
7,967 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

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 Oregon to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Oregon?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Oregon. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

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

    The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as $108. However, be on the lookout for offers from Delta and WestJet, as they are both options that can get you from Oregon to Winnipeg for a low price.

  • Can I find deals for flights from Oregon to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Oregon to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Winnipeg.

  • Can I find deals for business class flights from Oregon to Winnipeg?

    Yes. Cheapflights offers flight deals from Oregon to Winnipeg 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 Oregon to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of $358). Flying from Oregon to Winnipeg in December is currently the most expensive (average of $497). 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
Portage la Prairie

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Top 4 airlines flying from Oregon to Winnipeg

Discover the top 4 airlines that operate flights from Oregon to Winnipeg. 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 July 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$150Average$298FlexibilityNo cancel feeOn-time60%
DeltaCheapest$160Average$443FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$175Average$352FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$211Average$317FlexibilityNo cancel feeOn-time69%

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