$156 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
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Flight Deals

Cheap Flights from Winnipeg to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$274
Medford
Medford2 stops$632
Portland
Portland1 stop$274
Medford
Medford2 stops$632

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

Sun, May 10 - Sun, May 17
Multiple Airlines Logo
10:10 am - 1:50 pm
YWG
-
PDX
5h 40m
1 stop
Multiple Airlines Logo
12:52 pm - 12:40 am
PDX
-
YWG
9h 48m
1 stop
$274Multiple Airlines
Sun, May 10 - Sun, May 17
WestJet Logo
10:30 pm - 1:50 pm
YWG
-
PDX
17h 20m
2 stops
WestJet Logo
2:30 pm - 12:15 pm
PDX
-
YWG
19h 45m
1 stop
$285WestJet
Sun, May 10 - Sun, May 17
WestJet Logo
10:30 pm - 1:50 pm
YWG
-
PDX
17h 20m
2 stops
WestJet Logo
2:30 pm - 9:20 am
PDX
-
YWG
16h 50m
2 stops
$293WestJet
Fri, May 1 - Sun, May 3
United Airlines Logo
2:00 pm - 12:34 pm
YWG
-
PDX
24h 34m
2 stops
United Airlines Logo
5:00 am - 8:57 pm
PDX
-
YWG
13h 57m
1 stop
$298United Airlines
Fri, May 1 - Sun, May 3
United Airlines Logo
2:00 pm - 12:34 pm
YWG
-
PDX
24h 34m
2 stops
United Airlines Logo
5:00 am - 8:57 pm
PDX
-
YWG
13h 57m
1 stop
$299United Airlines
Fri, May 1 - Sun, May 3
Air Canada Logo
5:45 am - 9:30 am
YWG
-
PDX
5h 45m
1 stop
Air Canada Logo
7:45 pm - 1:04 pm
PDX
-
YWG
15h 19m
1 stop
$325Air Canada
Sun, Jun 7 - Sat, Jun 13
Delta Logo
5:38 pm - 11:34 pm
YWG
-
PDX
7h 56m
1 stop
Delta Logo
12:40 am - 11:34 am
PDX
-
YWG
8h 54m
1 stop
$326Delta
Wed, Apr 8 - Tue, Apr 14
Air Canada Logo
10:45 am - 2:40 pm
YWG
-
PDX
5h 55m
1 stop
Air Canada Logo
9:50 am - 9:20 pm
PDX
-
YWG
9h 30m
2 stops
$337Air Canada
Tue, Mar 10 - Mon, Mar 16
Delta Logo
11:55 am - 8:25 pm
YWG
-
PDX
10h 30m
1 stop
Delta Logo
12:30 am - 11:01 am
PDX
-
YWG
8h 31m
1 stop
$346Delta
Tue, Mar 10 - Mon, Mar 16
Delta Logo
11:55 am - 5:39 pm
YWG
-
PDX
7h 44m
1 stop
Delta Logo
12:30 am - 11:01 am
PDX
-
YWG
8h 31m
1 stop
$347Delta
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 $261 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $463 and $429 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$156
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 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 10712 reviews
7.1Comfort
6.8Entertainment
6.3Food
7.3Boarding
7.8Crew
Airline reviews

they were super helpful. Agents at the desk got me on an earlier flight and I was able to get home several hours earlier.

10.0 ExcellentBeth, Feb 2026
YVR - PDX
Read more Air Canada reviews

they were super helpful. Agents at the desk got me on an earlier flight and I was able to get home several hours earlier.

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

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

Information on your arrival and departure airports

Winnipeg (YWG)