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$106+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
1 adult, Economy
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Cheap 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 May 5, 2026.

This Trip.com deal was found by Cheapflights users on 5/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:30 pm
PDX
-
YWG
1 stop7h 10m
WestJet
Tue 8/257:00 am
YWG
-
PDX
2 stops8h 50m
WestJet
Deal found 5/3$236
This Trip.com deal was found by Cheapflights users on 5/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:30 pm
PDX
-
YWG
1 stop7h 10m
WestJet
Wed 8/2610:10 am
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 5/1$238
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/162:30 pm
PDX
-
YWG
1 stop7h 10m
WestJet
Mon 8/2410:10 am
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 5/3$248
This FlightHub deal was found by Cheapflights users on 4/30. 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.
Sun 8/162:30 pm
PDX
-
YWG
1 stop7h 10m
WestJet
Sun 8/2310:10 am
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 4/30$263
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:30 pm
PDX
-
YWG
1 stop7h 10m
WestJet
Tue 8/257:00 am
YWG
-
PDX
2 stops8h 50m
WestJet
Deal found 5/4$264
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:30 pm
PDX
-
YWG
1 stop7h 10m
WestJet
Mon 8/2410:10 am
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 5/4$273
This FlightHub deal was found by Cheapflights users on 5/4. 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.
Mon 8/172:30 pm
PDX
-
YWG
1 stop7h 10m
WestJet
Tue 8/2510:10 am
YWG
-
PDX
1 stop5h 40m
WestJet
Deal found 5/4$282

Find flight deals from Oregon to Winnipeg

Keep the following information in mind while searching for Oregon to Winnipeg flight deals. Data was last updated May 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$236
(Trip.com)

One-way from

$106
(Trip.com)

Popular in

February

Cheapest in

November

Average price

$469
Provider with most accurate pricing for Portland-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Winnipeg flights.
Search Deals
From Oregon to Winnipeg
Search Deals
One-way flight from Oregon to Winnipeg
Search Deals
Highest demand for flights based on searches. 26% potential increase in price ($158 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 5, 2026.
Use the filters below to find and compare flights from Oregon to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 8/16

2:30 pm-11:40 pm

1 stop7h 10m

Winnipeg

Sun 8/23

10:10 am-1:50 pm

1 stop5h 40m

$263
Quickest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 8/26

2:30 pm-10:10 pm

1 stop5h 40m

Winnipeg

Sat 8/29

10:10 am-1:50 pm

1 stop5h 40m

$294

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 5/20

2:30 pm-10:10 pm

1 stop5h 40m

Winnipeg

Mon 5/25

7:10 pm-1:50 pm

1 stop20h 40m

$351

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 6/6

3:30 pm-11:49 pm

1 stop6h 19m

Winnipeg

Mon 6/8

10:55 am-2:45 pm

1 stop5h 50m

$360

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 5/22

10:40 pm-11:52 am

1 stop11h 12m

Winnipeg

Tue 6/2

8:45 am-3:13 pm

1 stop8h 28m

$363

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Tue 5/26

11:58 am-11:26 pm

1 stop9h 28m

Winnipeg

Fri 5/29

11:55 am-8:11 pm

1 stop10h 16m

$373

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 5/22

10:40 pm-11:52 am

1 stop11h 12m

Winnipeg

Fri 5/29

8:45 am-11:00 pm

1 stop16h 15m

$373

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 6/6

9:20 am-11:26 pm

2 stops12h 06m

Winnipeg

Mon 6/8

6:40 am-10:39 am

1 stop5h 59m

$471

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 5/22

10:40 pm-11:52 am

1 stop11h 12m

Winnipeg

Sun 5/31

8:45 am-1:06 pm

1 stop6h 21m

$524

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 5/27

5:00 am-10:38 pm

2 stops15h 38m

Winnipeg

Thu 5/28

8:45 am-11:00 pm

1 stop16h 15m

$550

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

Showing 1-10 of 18 resultsSorted by cheapest first
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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, July is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of $88). Flying from Oregon to Winnipeg in April is currently the most expensive (average of $638). 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.

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

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.

  • How long is the flight from Oregon to Winnipeg?

    WestJet can get you from Oregon to Winnipeg in just under 7h 10m. Your travel time can differ by up to . The distance between Oregon and Winnipeg is about 1208 mi.

  • 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, July is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of $88). Flying from Oregon to Winnipeg in April is currently the most expensive (average of $638). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Oregon to Winnipeg

Discover the top 3 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 May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$88Average$377FlexibilityNo cancel feeOn-time60%
DeltaCheapest$188Average$424FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$203Average$365FlexibilityNo cancel feeOn-time67%

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