C$ 203 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 24/6. 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
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Flight Deals

Best Oregon Flight Deals from Winnipeg

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stopC$ 381
Medford
Medford2 stopsC$ 659
Portland
Portland1 stopC$ 381
Medford
Medford2 stopsC$ 659

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

Sat, 6 Jun - Tue, 9 Jun
United Airlines Logo
7:00 a.m. - 11:53 p.m.
YWG
-
PDX
18h 53m
1 stop
United Airlines Logo
5:00 a.m. - 8:57 p.m.
PDX
-
YWG
13h 57m
1 stop
C$ 381United Airlines
Sat, 6 Jun - Tue, 9 Jun
United Airlines Logo
7:00 a.m. - 6:47 p.m.
YWG
-
PDX
13h 47m
1 stop
United Airlines Logo
5:00 a.m. - 8:57 p.m.
PDX
-
YWG
13h 57m
1 stop
C$ 383United Airlines
Sat, 6 Jun - Tue, 9 Jun
United Airlines Logo
7:00 a.m. - 11:53 p.m.
YWG
-
PDX
18h 53m
1 stop
United Airlines Logo
5:00 a.m. - 8:57 p.m.
PDX
-
YWG
13h 57m
1 stop
C$ 402United Airlines
Thu, 25 Jun - Tue, 30 Jun
Air Canada Logo
5:30 a.m. - 9:31 a.m.
YWG
-
PDX
6h 01m
1 stop
Air Canada Logo
7:45 p.m. - 1:10 p.m.
PDX
-
YWG
15h 25m
1 stop
C$ 404Air Canada
Wed, 24 Jun - Tue, 30 Jun
Air Canada Logo
5:30 a.m. - 9:31 a.m.
YWG
-
PDX
6h 01m
1 stop
Air Canada Logo
7:45 p.m. - 12:17 p.m.
PDX
-
YWG
14h 32m
2 stops
C$ 426Air Canada
Sat, 6 Jun - Tue, 9 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. - 12:20 p.m.
PDX
-
YWG
14h 35m
2 stops
C$ 433Air Canada
Sat, 6 Jun - Tue, 9 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. - 12:20 p.m.
PDX
-
YWG
14h 35m
2 stops
C$ 454Air Canada
Tue, 2 Jun - Sat, 6 Jun
Delta Logo
3:50 p.m. - 12:58 p.m.
YWG
-
MFR
23h 08m
2 stops
Delta Logo
6:15 a.m. - 11:26 p.m.
MFR
-
YWG
15h 11m
2 stops
C$ 659Delta
Tue, 2 Jun - Sat, 6 Jun
Delta Logo
3:50 p.m. - 12:58 p.m.
YWG
-
MFR
23h 08m
2 stops
Delta Logo
5:15 a.m. - 11:26 p.m.
MFR
-
YWG
16h 11m
2 stops
C$ 674Delta
Tue, 2 Jun - Sat, 6 Jun
Delta Logo
5:41 p.m. - 12:58 p.m.
YWG
-
MFR
21h 17m
2 stops
Delta Logo
6:15 a.m. - 11:26 p.m.
MFR
-
YWG
15h 11m
2 stops
C$ 685Delta
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 June.

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$ 312 (return) on average. On the other hand, the most expensive months are March and February, when the average cost of round-trip tickets is C$ 796 and C$ 700 respectively.

Good to know

Low seasonJanuary
Cheapest flightC$ 203
Best time to beat the crowds (5% less expensive on average)
Most popular time to fly and prices are also 37% 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 airlines 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.
7.2
WestJetOverall score based on 3316 reviews
6.2Food
7.0Comfort
7.9Crew
6.1Entertainment
7.4Boarding
Airline reviews

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

10.0 ExcellentAnonymous, Mar 2026
YLW - SEA
Read more WestJet reviews

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

The window seat on the emergency row was too small. I had a different seat booked and they moved me. My seat remained open. It was very uncomfortable.

Experience was good, the wifi hook up is somewhat tough

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

Overall good experience. The wait for baggage at our destination was quite long, but other than that everything was good as expected

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

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.

The flight was delayed, but not for weather. We landed over 3hrs later than planned.

The stag were helpful, kind and liked the passengers. The plane was pristinely clean! Great flight!

My flight was delayed more than once, but Air Canada updated us regularly. Friends on other airlines had much worse experiences.

My ticket did not exist when I got to the airport. I had to book another flight and was still charged by Kayak

Got denied my flight was told on Google that Air Canada was supposed to book me a flight back home because I never was able to go to my destination. They did not help me whatsoever. I had to book a whole new flight for that reason I would write this is zero

The plane was delayed an hour. Heard from other passengers that the Vancouver connection to SFO was never on-time.

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

Information on your arrival and departure airports