C$ 299 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 28/11. 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

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$ 409
Medford
Medford2 stopsC$ 734
Portland
Portland1 stopC$ 409
Medford
Medford2 stopsC$ 734

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

Thu, 18 Dec - Thu, 1 Jan
Air Canada Logo
10:45 a.m. - 2:40 p.m.YWG-PDX
5h 55m1 stop
Air Canada Logo
3:15 p.m. - 1:14 a.m.PDX-YWG
7h 59m1 stop
C$ 409Air Canada
Find Deal
Wed, 4 Mar - Thu, 5 Mar
Air Canada Logo
10:45 a.m. - 2:40 p.m.YWG-PDX
5h 55m1 stop
Air Canada Logo
9:50 a.m. - 6:09 p.m.PDX-YWG
6h 19m1 stop
C$ 420Air Canada
Find Deal
Wed, 24 Dec - Sun, 28 Dec
Air Canada Logo
9:40 p.m. - 9:15 a.m.YWG-PDX
13h 35m1 stop
Air Canada Logo
3:15 p.m. - 1:14 a.m.PDX-YWG
7h 59m1 stop
C$ 472Air Canada
Find Deal
Fri, 7 Nov - Thu, 13 Nov
Multiple Airlines Logo
5:35 p.m. - 9:40 a.m.YWG-PDX
18h 05m1 stop
Multiple Airlines Logo
12:52 p.m. - 1:23 a.m.PDX-YWG
34h 31m2 stops
C$ 681Multiple Airlines
Find Deal
Wed, 24 Dec - Sun, 28 Dec
WestJet Logo
6:45 a.m. - 11:05 a.m.YWG-PDX
30h 20m2 stops
WestJet Logo
9:19 a.m. - 10:41 p.m.PDX-YWG
11h 22m2 stops
C$ 699WestJet
Find Deal
Wed, 24 Dec - Wed, 31 Dec
Delta Logo
6:40 a.m. - 9:14 p.m.YWG-MFR
16h 34m2 stops
Delta Logo
12:36 p.m. - 10:41 p.m.MFR-YWG
8h 05m2 stops
C$ 734Delta
Find Deal
Thu, 18 Dec - Thu, 1 Jan
Multiple Airlines Logo
2:40 p.m. - 6:50 p.m.YWG-PDX
30h 10m2 stops
Multiple Airlines Logo
6:14 a.m. - 12:41 a.m.PDX-YWG
16h 27m2 stops
C$ 736Multiple Airlines
Find Deal
Thu, 18 Dec - Thu, 1 Jan
WestJet Logo
2:40 p.m. - 6:50 p.m.YWG-PDX
30h 10m2 stops
WestJet Logo
2:11 p.m. - 8:06 p.m.PDX-YWG
27h 55m2 stops
C$ 741WestJet
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Wed, 24 Dec - Wed, 31 Dec
United Airlines Logo
8:40 a.m. - 9:12 p.m.YWG-MFR
14h 32m1 stop
United Airlines Logo
5:00 a.m. - 8:51 p.m.MFR-YWG
13h 51m1 stop
C$ 1,052United Airlines
Find Deal
Fri, 7 Nov - Thu, 13 Nov
United Airlines Logo
5:30 p.m. - 10:45 p.m.YWG-PDX
31h 15m2 stops
United Airlines Logo
1:00 p.m. - 11:57 a.m.PDX-YWG
20h 57m3 stops
C$ 1,059United Airlines
Find Deal
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.

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 July, when tickets cost C$ 378 (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$ 602 and C$ 590 respectively.

What’s the cheapest day of the week to fly from Winnipeg to Oregon?

The average price of all round-trip flights from Winnipeg to Oregon clicked on KAYAK for each day over the last 12 months.

When flying from Winnipeg to Oregon, you should consider leaving on a Sunday and avoid Mondays if you are looking for the best rates. For your return to Winnipeg, you’ll find the best rates on Thursdays and the most expensive ones on Fridays.

Good to know

Low seasonSeptember
Cheapest flightC$ 299
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly and prices are also 15% 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.

  • What is the cheapest time of day to fly to Oregon?

    The cheapest time of day to fly to Oregon is generally at night, when round-trip flights cost C$ 290 on average. Morning departures are around 15% more expensive than evening flights, on average. The most expensive time of day to fly to Oregon is generally in the morning, which is peak travel time and where the average cost of a ticket is C$ 410.

Reviews of the top 3 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.
7.4
United AirlinesOverall score based on 8982 reviews
7.3Comfort
7.1Entertainment
7.7Boarding
6.6Food
8.1Crew
Airline reviews

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

8.0 ExcellentCynthia, Oct 2025ORD - PDX
Read more United Airlines reviews

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Do not fly on WestJet if you have a connection. It failed to integrate with my connecting Delta flight and I almost missed it.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

A little better seat cushions would be appreciated. Crews were all good.

The process and flight were both smooth and trouble free

Flight delayed 3 hours, missed my connection in Atlanta. Instead of getting to Savannah at 6PM arrived after 10:00PM Middle seat, couldn't get isle or window, couldn't book my seats in advance, had to book at the gate. That's a 1st for me and I used to travel a lot

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

taking our carryon and forcing us to check it through

Wifi was great. Kind air crew and comfortable seating. Also liked the entertainment options.

Great flight. Only complaint is it took over an hour for my luggage to get to the carousel on the return to LAX That was irritating

I knew I was going to fall asleep unsettlingly from exhaustion so I warned the guy next to me in advance. The attendant took to checking on me frequently and even insisted I take my snack because I said no while sleep hazed and then absolutely wanted it about 5 minutes later. He was So caring and kind to my situation!!

First message when all on board was that we didnt have a pilot, then they found one, then it was something about the bridge something not working, they will either fix or do manually. Flight of course was leaving late with all the cruise guests worrying about making it to their ship in time. Then only some luggage made it off the ship. Around 15 to 20 people waiting. 45 min later arrived except mine. I asked the rep at the luggage conveyor, he asked me my name. Then said it was not picked up with the first batch so they put it in a room. I was going to take public transport but now worried about time so took a taxi that cost me $65 USD

The flight was very smooth and good. Boarding was fast, but the staff was just decently friendly.

Air Canada flight staff are in contact negotiations and they are less than happy and it show. The process of self checking baggage is less than desirable with lack of support staff to help

A sandwich and a drink would have been better thank a snack bar...

I liked the behaviour of the crew members.The flight was good.

1 hour late No hot drinks No restroom in the back of the plane

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

Information on your arrival and departure airports

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