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$163+ Cheap flights from Winnipeg (YWG) to Oregon

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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
1 adult, Economy
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Cheap flight deals from Winnipeg to Oregon

Cheapest flights from Winnipeg to Oregon
Explore the most affordable flight options available from Winnipeg to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 24, 2026.

This Delta deal was found by Cheapflights users on 3/21. 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 4/1011:55 am
YWG
-
PDX
1 stop10h 30m
Delta
Fri 4/1712:30 am
PDX
-
YWG
1 stop8h 26m
Delta
Deal found 3/21$308
This Air Canada deal was found by Cheapflights users on 3/24. 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.
Sat 6/205:40 am
YWG
-
PDX
1 stop5h 51m
Air Canada
Mon 6/227:45 pm
PDX
-
YWG
1 stop15h 25m
Air Canada
Deal found 3/24$320
This Air Canada deal was found by Cheapflights users on 3/19. 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.
Sun 6/75:45 am
YWG
-
PDX
1 stop5h 45m
Air Canada
Sun 6/143:30 pm
PDX
-
YWG
2 stops18h 50m
Air Canada
Deal found 3/19$339
This United Airlines deal was found by Cheapflights users on 3/23. 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.
Sat 5/28:45 am
YWG
-
PDX
1 stop14h 24m
United Airlines
Tue 5/51:37 pm
PDX
-
YWG
2 stops20h 15m
United Airlines
Deal found 3/23$342
This Air Canada deal was found by Cheapflights users on 3/22. 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.
Mon 5/115:40 am
YWG
-
PDX
1 stop5h 50m
Air Canada
Mon 5/117:45 pm
PDX
-
YWG
1 stop15h 19m
Air Canada
Deal found 3/22$345
This Trip.com deal was found by Cheapflights users on 3/19. 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.
Sun 4/2610:15 pm
YWG
-
PDX
1 stop12h 55m
Air Canada
Sun 5/243:30 pm
PDX
-
YWG
1 stop8h 34m
Air Canada
Deal found 3/19$347
This Air Canada deal was found by Cheapflights users on 3/24. 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.
Fri 6/195:40 am
YWG
-
PDX
1 stop15h 26m
Air Canada
Mon 6/227:45 pm
PDX
-
YWG
1 stop15h 25m
Air Canada
Deal found 3/24$351
This United Airlines deal was found by Cheapflights users on 3/21. 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.
Sat 4/258:45 am
YWG
-
PDX
1 stop11h 00m
United Airlines
Fri 5/87:45 pm
PDX
-
YWG
2 stops14h 07m
United Airlines
Deal found 3/21$365
This Air Canada deal was found by Cheapflights users on 3/22. 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 5/57:20 am
YWG
-
PDX
2 stops9h 25m
Air Canada
Sat 5/97:45 pm
PDX
-
YWG
1 stop15h 19m
Air Canada
Deal found 3/22$367
This United Airlines deal was found by Cheapflights users on 3/19. 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.
Fri 5/12:00 pm
YWG
-
MFR
2 stops23h 47m
United Airlines
Sat 5/22:07 pm
MFR
-
YWG
3 stops28h 50m
United Airlines
Deal found 3/19$604
This United Airlines deal was found by Cheapflights users on 3/23. 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.
Sat 5/28:45 am
YWG
-
MFR
2 stops29h 02m
United Airlines
Tue 5/52:07 pm
MFR
-
YWG
2 stops19h 45m
United Airlines
Deal found 3/23$605

Find flight deals from Winnipeg to Oregon

Keep the following information in mind while searching for Winnipeg to Oregon flight deals. Data was last updated March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$308
(Delta)

One-way from

$163
(Air Canada)

Popular in

February

Cheapest in

August

Average price

$460
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 Oregon
Search Deals
One-way flight from Winnipeg to Oregon
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Oregon 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 March 24, 2026.
Use the filters below to find and compare flights from Winnipeg to Oregon that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 6/20

5:40 am-9:31 am

1 stop5h 51m

Portland

Mon 6/22

7:45 pm-1:10 pm

1 stop15h 25m

$320

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 6/7

5:45 am-9:30 am

1 stop5h 45m

Portland

Sun 6/14

3:30 pm-12:20 pm

2 stops18h 50m

$339

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 5/2

8:45 am-9:09 pm

1 stop14h 24m

Portland

Tue 5/5

1:37 pm-11:52 am

2 stops20h 15m

$342

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 6/19

5:40 am-7:06 pm

1 stop15h 26m

Portland

Mon 6/22

7:45 pm-1:10 pm

1 stop15h 25m

$351
Quickest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 6/7

3:54 pm-11:21 pm

1 stop9h 27m

Portland

Sun 6/14

6:00 am-4:52 pm

1 stop8h 52m

$365

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 4/25

8:45 am-12:44 am

2 stops17h 59m

Portland

Fri 5/8

3:59 pm-11:52 am

2 stops17h 53m

$365

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 5/5

5:40 am-9:30 am

1 stop5h 50m

Portland

Sat 5/9

7:45 pm-1:04 pm

1 stop15h 19m

$367

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 4/16

8:45 am-10:54 pm

1 stop16h 09m

Portland

Thu 4/23

4:15 pm-11:52 am

2 stops17h 37m

$389

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Fri 5/1

2:00 pm-11:47 am

2 stops23h 47m

Medford

Sat 5/2

2:07 pm-8:57 pm

3 stops28h 50m

$604

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Sat 5/2

8:45 am-1:01 pm

1 stop6h 16m

Medford

Tue 5/5

2:07 pm-11:52 am

2 stops19h 45m

$605

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

Best time to book a flight from Winnipeg to Oregon

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

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

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Oregon (average of $137). Flying from Winnipeg to Oregon in June is currently the most expensive (average of $383). 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.

Reviews of airlines servicing Oregon

Get insights into the airlines that provide service to Oregon. 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 Oregon. Reviews last updated March 24, 2026.
Read through reviews of airlines operating flights from Winnipeg to Oregon, such as Air Canada. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,836 reviews

Overall

7.1

Crew

7.8

Boarding

7.3

Comfort

7.1

Entertainment

6.8

Food

6.3

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.
Air Canada
7.1
Good
10,836 reviews
Air Canada
7.1
Good
10,836 reviews

Overall

7.1

Crew

7.8

Boarding

7.3

Comfort

7.1

Entertainment

6.8

Food

6.3

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Oregon. 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 from for flights from Winnipeg to Oregon?

    Located just 4.6 mi from the city center, Winnipeg (YWG) is the airport most travelers will use when flying to Oregon from Winnipeg.

  • How long is the flight from Winnipeg to Oregon?

    There are many flights that can get you from Winnipeg to Oregon in 5h 51m. Fly via Air Canada, United Airlines, or Delta to get the fastest option. Airlines will cover a distance of 1208 mi. This flight may include one or multiple stops.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Winnipeg to Oregon (average of $137). Flying from Winnipeg to Oregon in June is currently the most expensive (average of $383). 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

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.

Top airline flying from Winnipeg to Oregon

Discover the top airline that operate flights from Winnipeg to Oregon. 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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$214Average$369FlexibilityNo cancel feeOn-time67%

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