C$ 245 Find Cheap Flights from Winnipeg to Oregon

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Oregon departing on 6/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Oregon

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Oregon, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Oregon, as well as popular online travel agencies
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Best Oregon Flight Deals from Winnipeg

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland2 stopsC$ 388
Medford
Medford2 stopsC$ 871
Portland
Portland2 stopsC$ 388
Medford
Medford2 stopsC$ 871

Cheap Flights from Winnipeg to Oregon

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Oregon that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Oregon

Tue, 20 Oct - Sat, 24 Oct
Air Canada Logo
7:20 a.m. - 2:51 p.m.
YWG
-
PDX
9h 31m
2 stops
Air Canada Logo
10:10 a.m. - 5:47 p.m.
PDX
-
YWG
5h 37m
1 stop
C$ 388Air Canada
Tue, 20 Oct - Sat, 24 Oct
United Airlines Logo
8:30 a.m. - 10:52 p.m.
YWG
-
PDX
16h 22m
1 stop
United Airlines Logo
10:43 a.m. - 8:48 p.m.
PDX
-
YWG
8h 05m
1 stop
C$ 397United Airlines
Fri, 14 Aug - Mon, 24 Aug
Air Canada Logo
5:40 a.m. - 9:31 a.m.
YWG
-
PDX
5h 51m
1 stop
Air Canada Logo
7:45 p.m. - 1:10 p.m.
PDX
-
YWG
15h 25m
1 stop
C$ 421Air Canada
Fri, 5 Jun - Mon, 8 Jun
Air Canada Logo
5:40 a.m. - 9:30 a.m.
YWG
-
PDX
5h 50m
1 stop
Air Canada Logo
7:45 p.m. - 1:04 p.m.
PDX
-
YWG
15h 19m
1 stop
C$ 435Air Canada
Wed, 17 Jun - Tue, 23 Jun
Air Canada Logo
7:20 a.m. - 2:45 p.m.
YWG
-
PDX
9h 25m
2 stops
Air Canada Logo
7:45 p.m. - 12:17 p.m.
PDX
-
YWG
14h 32m
2 stops
C$ 481Air Canada
Fri, 14 Aug - Mon, 24 Aug
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
WestJet Logo
2:30 p.m. - 12:00 p.m.
PDX
-
YWG
19h 30m
2 stops
C$ 566WestJet
Fri, 12 Jun - Wed, 17 Jun
Delta Logo
12:46 p.m. - 8:17 p.m.
YWG
-
PDX
9h 31m
1 stop
Delta Logo
6:00 a.m. - 4:51 p.m.
PDX
-
YWG
8h 51m
1 stop
C$ 585Delta
Fri, 5 Jun - Mon, 8 Jun
WestJet Logo
7:00 a.m. - 1:50 p.m.
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 p.m. - 11:10 a.m.
PDX
-
YWG
18h 40m
1 stop
C$ 588WestJet
Fri, 14 Aug - Mon, 24 Aug
WestJet Logo
7:00 a.m. - 1:50 p.m.
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 p.m. - 2:40 p.m.
PDX
-
YWG
22h 10m
2 stops
C$ 589WestJet
Fri, 12 Jun - Thu, 18 Jun
Multiple Airlines Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
Multiple Airlines Logo
8:42 p.m. - 12:40 a.m.
PDX
-
YWG
25h 58m
1 stop
C$ 591Multiple Airlines
Booking Insights

KAYAK's insights & trends for Winnipeg to Oregon flights

Get data-powered insights and trends into flights from Winnipeg to Oregon to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Winnipeg to Oregon?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Winnipeg to Oregon departing in October.

What is the cheapest month to fly from Winnipeg to Oregon?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Oregon, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Winnipeg to Oregon is August, when tickets cost C$ 167 (return) on average. On the other hand, the most expensive months are June and January, when the average cost of round-trip tickets is C$ 513 and C$ 472 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flightC$ 245
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly and prices are also 31% lower on average.
Flight from Winnipeg to Portland

FAQs - booking Oregon flights

  • How does KAYAK find such low prices on flights from Winnipeg to Oregon?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Oregon.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Oregon?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Winnipeg to Oregon is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Winnipeg to Oregon?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Winnipeg to Oregon with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Oregon?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Winnipeg to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Winnipeg to Oregon

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to Oregon. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Winnipeg to Oregon? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
Air CanadaOverall score based on 11019 reviews
7.1Comfort
7.8Crew
7.3Boarding
6.3Food
6.8Entertainment
Airline reviews

Flight Boarded and departed on time. The Flight crew was very friendly and accommodating. The aircraft was clean and free from clutter and debris. I will be happy to recommend Air Canada to my friends and relatives for their flight needs. They were very attentive and responsive to our needs as Senior citizens.

10.0 ExcellentGkuhio, May 2026
YVR - HNL
Read more Air Canada reviews

Flight Boarded and departed on time. The Flight crew was very friendly and accommodating. The aircraft was clean and free from clutter and debris. I will be happy to recommend Air Canada to my friends and relatives for their flight needs. They were very attentive and responsive to our needs as Senior citizens.

Another good flight experience with Air Canada. The business section did not feature the full length sleeping arrangement, but this was a shorter trip. The food was excellent. But the flight crew was truly top tier: friendly, cheerful, helpful at all the right times. Air Canada truly outshines all U.S. carriers.

Flight operated by PAL. We boarded, and one engine started. The crew found some problem that could not be fixed. The flight was canceled. This run from yhz-bos is very unreliable.

Everything. The crew was so friendly, helpful & smiled. We had an excellent flight getting in earlier.

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

Flight and attendance were very good we had 2 hour delay that took the shine of it

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

Be careful about the bad policy and when purchasing seats

Very disappointed with premier lounge. Food selection very poor, both coffee machines out of order. For the price you charge for an upgrade, the seats don’t fully recline, movie selection is old. Not very good value. Asian airlines are light years ahead at a more affordable price.

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

Everything you need to know for your flight from Winnipeg to Oregon

Information on your arrival and departure airports

Winnipeg (YWG)