C$ 291 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 24/3. 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$ 324
Medford
Medford2 stopsC$ 893
Portland
Portland1 stopC$ 324
Medford
Medford2 stopsC$ 893

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

Mon, 18 May - Sun, 24 May
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
C$ 324WestJet
Mon, 18 May - Sat, 23 May
WestJet Logo
12:50 p.m. - 1:50 p.m.
YWG
-
PDX
27h 00m
2 stops
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
C$ 358WestJet
Mon, 18 May - Sat, 23 May
WestJet Logo
7:00 a.m. - 1:50 p.m.
YWG
-
PDX
8h 50m
1 stop
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
C$ 366WestJet
Mon, 18 May - Sat, 23 May
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$ 391WestJet
Mon, 18 May - Sun, 24 May
WestJet Logo
10:15 p.m. - 1:50 p.m.
YWG
-
PDX
17h 35m
2 stops
WestJet Logo
2:30 p.m. - 2:40 p.m.
PDX
-
YWG
22h 10m
2 stops
C$ 403WestJet
Mon, 18 May - Sat, 23 May
WestJet Logo
10:15 p.m. - 1:50 p.m.
YWG
-
PDX
17h 35m
2 stops
WestJet Logo
2:30 p.m. - 2:40 p.m.
PDX
-
YWG
22h 10m
2 stops
C$ 428WestJet
Mon, 15 Jun - Sat, 20 Jun
WestJet Logo
7:10 p.m. - 1:50 p.m.
YWG
-
PDX
20h 40m
1 stop
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
C$ 431WestJet
Mon, 18 May - Sat, 23 May
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
C$ 435WestJet
Tue, 3 Mar - Thu, 5 Mar
Delta Logo
11:53 a.m. - 10:50 a.m.
YWG
-
MFR
24h 57m
2 stops
Delta Logo
5:22 p.m. - 4:27 p.m.
MFR
-
YWG
21h 05m
2 stops
C$ 893Delta
Tue, 3 Mar - Thu, 5 Mar
United Airlines Logo
2:20 p.m. - 10:56 a.m.
YWG
-
MFR
22h 36m
2 stops
United Airlines Logo
2:00 p.m. - 11:57 a.m.
MFR
-
YWG
19h 57m
2 stops
C$ 939United 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.

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$ 357 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is C$ 633 and C$ 586 respectively.

Good to know

Low seasonJanuary
Cheapest flightC$ 291
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 16% 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 3256 reviews
6.1Entertainment
6.2Food
7.0Comfort
7.4Boarding
7.9Crew
Airline reviews

Experience was good, the wifi hook up is somewhat tough

10.0 ExcellentAnonymous, Jan 2026
YYZ - LAS
Read more WestJet reviews

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.

I was seated near a "stinky" person. That's not the fault of Westjet🙁😶‍🌫️

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

This is a great non-stop YVR-MIA. Very comfortable plane, and no transfer through a city that gets major winter weather!

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

Air Canada’s problems are not staff related by and large, no. The problem is tiny jets between the U.S. and Canada - yes, believe it or not they are still “international” (just ask our own Mango Maniac in power in the U.S.). The little aisle is compounded by a design flaw of a “dog leg” starting at seat 12. Woe be unto you if you sit here as passengers and attendants do not have sufficient room to not hit you in the face with backpacks. One thing I will say very positively about Air Canada is you still provide pillows and blankets on transcontinental flights to all, not just the elites. Your tiny improperly designed jets are also a problem flying city to city within Canada also. One can only say you remind us of a “Jet Blue” or “Spirit” experience. Also your luggage space is downright Byzantine! We will endeavor to avoid you and use other U.S. carriers, albeit charging more.

Terrible canceled flight and lost my luggage. Flew me to Halifax. Tgat flight was delayed, had to spend night in airport chair.

My seat was not comfortable. Flight was smooth. Regretfully we had two delays before takeoff

Amazing service, with enthusiastic crew members, and some breathtaking views of Vancouver. No IFE though, as it is only a 1 hour flight on a regional Turboprop jet.

I like the fact air Canada is on time The food you guys serve is not good

They are very proactive and made our boarding easy and always notified us about any changes well in advance.

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

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

Information on your arrival and departure airports