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Oregon

$177+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Jul 28 — Aug 41
Tue 7/28
Tue 8/4
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 June 28, 2026.

This oojo deal was found by Cheapflights users on 6/27. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:00 am
YWG
-
PDX
2 stops8h 50m
WestJet
Sun 9/132:30 pm
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 6/27$248
This Air Canada deal was found by Cheapflights users on 6/26. 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 9/197:20 am
YWG
-
PDX
2 stops9h 26m
Air Canada
Mon 9/217:45 pm
PDX
-
YWG
1 stop5h 12m
Air Canada
Deal found 6/26$294
This Air Canada deal was found by Cheapflights users on 6/27. 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 9/105:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Sat 9/127:45 pm
PDX
-
YWG
1 stop5h 12m
Air Canada
Deal found 6/27$295
This United Airlines deal was found by Cheapflights users on 6/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:00 am
YWG
-
PDX
2 stops16h 10m
United Airlines
Sat 10/311:30 pm
PDX
-
YWG
1 stop11h 07m
United Airlines
Deal found 6/24$299
This United Airlines deal was found by Cheapflights users on 6/25. 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 9/107:00 am
YWG
-
PDX
2 stops19h 34m
United Airlines
Sat 9/128:40 am
PDX
-
YWG
2 stops11h 53m
United Airlines
Deal found 6/25$300
This United deal was found by Cheapflights users on 6/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:00 am
YWG
-
PDX
1 stop17h 52m
Multiple Airlines
Tue 9/17:45 pm
PDX
-
YWG
1 stop5h 12m
Multiple Airlines
Deal found 6/26$302
This Air Canada deal was found by Cheapflights users on 6/24. 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 8/115:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Tue 8/187:45 pm
PDX
-
YWG
1 stop5h 12m
Air Canada
Deal found 6/24$304
This United Airlines deal was found by Cheapflights users on 6/26. 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 8/277:00 am
YWG
-
PDX
1 stop17h 52m
United Airlines
Tue 9/110:50 am
PDX
-
YWG
2 stops23h 02m
United Airlines
Deal found 6/26$311
This Air Canada deal was found by Cheapflights users on 6/23. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Sat 8/227:45 pm
PDX
-
YWG
1 stop5h 12m
Air Canada
Deal found 6/23$315
This Delta deal was found by Cheapflights users on 6/24. 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.
Tue 9/223:58 pm
YWG
-
MFR
2 stops9h 19m
Delta
Sat 9/265:29 pm
MFR
-
YWG
2 stops16h 27m
Delta
Deal found 6/24$575
This Delta deal was found by Cheapflights users on 6/25. 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.
Tue 12/86:35 am
YWG
-
MFR
2 stops12h 08m
Delta
Wed 12/95:21 pm
MFR
-
YWG
2 stops16h 29m
Delta
Deal found 6/25$633
This United Airlines deal was found by Cheapflights users on 6/25. 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.
Tue 12/88:30 am
YWG
-
MFR
1 stop14h 40m
United Airlines
Wed 12/95:10 am
MFR
-
YWG
1 stop13h 38m
United Airlines
Deal found 6/25$660

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 June 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$248
(oojo)

One-way from

$177
(Air Canada)

Popular in

April

Cheapest in

August

Average price

$375
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. 15% potential increase in price ($74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 28, 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

Fri 9/11

7:00 am-1:50 pm

2 stops8h 50m

Portland

Sun 9/13

2:30 pm-10:10 pm

1 stop5h 40m

$248

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 9/19

7:20 am-2:46 pm

2 stops9h 26m

Portland

Mon 9/21

7:45 pm-2:57 am

1 stop5h 12m

$294
Quickest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 9/10

5:45 am-9:31 am

1 stop5h 46m

Portland

Sat 9/12

7:45 pm-2:57 am

1 stop5h 12m

$295

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 9/30

7:00 am-9:10 pm

2 stops16h 10m

Portland

Sat 10/3

11:30 pm-12:37 pm

1 stop11h 07m

$299

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 9/10

7:00 am-12:34 am

2 stops19h 34m

Portland

Sat 9/12

8:40 am-10:33 pm

2 stops11h 53m

$300

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 9/19

7:00 am-10:45 pm

2 stops17h 45m

Portland

Mon 9/21

11:02 pm-11:52 am

1 stop10h 50m

$300

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 8/27

7:00 am-10:52 pm

1 stop17h 52m

Portland

Tue 9/1

7:45 pm-2:57 am

1 stop5h 12m

$302

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 8/27

2:00 pm-9:32 am

2 stops21h 32m

Portland

Tue 9/1

10:50 am-11:52 am

2 stops23h 02m

$311

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Tue 9/22

3:58 pm-11:17 pm

2 stops9h 19m

Medford

Sat 9/26

5:29 pm-11:56 am

2 stops16h 27m

$575

WinnipegMedford

YWG - MFR

YWGMFR

Winnipeg

Tue 12/8

6:35 am-4:43 pm

2 stops12h 08m

Medford

Wed 12/9

5:21 pm-11:50 am

2 stops16h 29m

$633

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/25

Showing 1-10 of 17 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 $122). Flying from Winnipeg to Oregon in January is currently the most expensive (average of $345). 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 Winnipeg to Oregon?

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 June 28, 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
11,269 reviews

Entertainment

6.8

Overall

7.1

Food

6.3

Boarding

7.3

Comfort

7.1

Crew

7.8

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
11,269 reviews
Air Canada
7.1
Good
11,269 reviews

Entertainment

6.8

Overall

7.1

Food

6.3

Boarding

7.3

Comfort

7.1

Crew

7.8

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 8h 50m. Fly via WestJet, Air Canada, or United Airlines 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 $122). Flying from Winnipeg to Oregon in January is currently the most expensive (average of $345). 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 June 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$299Average$389FlexibilityNo cancel feeOn-time67%

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