$159 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 9/6. 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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Cheap Flights from Winnipeg to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland2 stops$228
Medford
Medford2 stops$596
Portland
Portland2 stops$228
Medford
Medford2 stops$596

Book Cheap Winnipeg to Oregon Plane Tickets

 
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, Jul 4 - Sun, Jul 12
WestJet Logo
7:00 am - 1:50 pm
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 pm - 11:40 pm
PDX
-
YWG
7h 10m
1 stop
$228WestJet
Sat, Jul 4 - Sun, Jul 12
WestJet Logo
10:10 am - 1:50 pm
YWG
-
PDX
5h 40m
1 stop
WestJet Logo
2:30 pm - 11:40 pm
PDX
-
YWG
7h 10m
1 stop
$230WestJet
Sat, Jul 4 - Sun, Jul 12
WestJet Logo
7:00 am - 1:50 pm
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 pm - 11:40 pm
PDX
-
YWG
7h 10m
1 stop
$231WestJet
Sat, Jul 4 - Sun, Jul 12
WestJet Logo
10:10 am - 1:50 pm
YWG
-
PDX
5h 40m
1 stop
WestJet Logo
2:30 pm - 10:10 pm
PDX
-
YWG
5h 40m
1 stop
$232WestJet
Sat, Jul 4 - Sun, Jul 12
WestJet Logo
7:00 am - 1:50 pm
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 pm - 4:00 pm
PDX
-
YWG
23h 30m
2 stops
$246WestJet
Wed, Jun 24 - Wed, Jul 15
Air Canada Logo
5:30 am - 9:31 am
YWG
-
PDX
6h 01m
1 stop
Air Canada Logo
7:45 pm - 3:02 am
PDX
-
YWG
5h 17m
1 stop
$279Air Canada
Tue, Oct 20 - Fri, Oct 23
Delta Logo
8:00 am - 11:12 pm
YWG
-
MFR
17h 12m
2 stops
Delta Logo
5:21 pm - 11:50 am
MFR
-
YWG
16h 29m
2 stops
$596Delta
Tue, Oct 20 - Fri, Oct 23
Delta Logo
8:00 am - 11:12 pm
YWG
-
MFR
17h 12m
2 stops
Delta Logo
12:25 pm - 11:50 am
MFR
-
YWG
21h 25m
2 stops
$597Delta
Thu, Sep 24 - Mon, Sep 28
United Airlines Logo
8:30 am - 9:08 pm
YWG
-
MFR
14h 38m
1 stop
United Airlines Logo
2:03 pm - 11:39 am
MFR
-
YWG
19h 36m
2 stops
$647United Airlines
Tue, Oct 20 - Fri, Oct 23
United Airlines Logo
8:30 am - 1:01 pm
YWG
-
MFR
6h 31m
1 stop
United Airlines Logo
2:03 pm - 11:39 am
MFR
-
YWG
19h 36m
2 stops
$648United 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 July.

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 $122 (return) on average. On the other hand, the most expensive months are January and February, when the average cost of round-trip tickets is $345 and $342 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$159
Best time to beat the crowds with an average 6% drop in price.
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 travelers 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 11075 reviews
6.3Food
7.3Boarding
6.8Entertainment
7.8Crew
7.1Comfort
Airline reviews

Never flown with Air Canada before, but it's now a top choice! Loved it!

10.0 ExcellentAnonymous, May 2026
YVR - PHX
Read more Air Canada reviews

Never flown with Air Canada before, but it's now a top choice! Loved it!

Horrible crew, horrible seats configuration, ridiculous space in the toilets, Air Canada is no longer a option.

Crew at gate and onboard were just very OK, not very friendly and honestly seemed bothered to be there. I will give a shout out to still selling headphones for those who forgot.

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.

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

Information on your arrival and departure airports

Winnipeg (YWG)