$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 3/4. 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
Portland2 stops$339
Medford
Medford2 stops$680
Portland
Portland2 stops$339
Medford
Medford2 stops$680

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, Feb 28 - Wed, Mar 4
United Airlines Logo
2:20 pm - 9:42 am
YWG
-
PDX
21h 22m
2 stops
United Airlines Logo
1:40 pm - 11:57 am
PDX
-
YWG
20h 17m
2 stops
$339United Airlines
Wed, Mar 4 - Wed, Mar 11
Air Canada Logo
10:40 am - 2:40 pm
YWG
-
PDX
6h 00m
1 stop
Air Canada Logo
9:50 am - 6:19 pm
PDX
-
YWG
6h 29m
1 stop
$370Air Canada
Tue, Feb 24 - Sat, Feb 28
Air Canada Logo
10:40 am - 2:40 pm
YWG
-
PDX
6h 00m
1 stop
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m
1 stop
$376Air Canada
Sat, Feb 28 - Wed, Mar 4
United Airlines Logo
2:20 pm - 10:56 pm
YWG
-
PDX
10h 36m
1 stop
United Airlines Logo
11:59 pm - 11:57 am
PDX
-
YWG
9h 58m
1 stop
$382United Airlines
Thu, Mar 26 - Sun, Mar 29
Air Canada Logo
10:10 pm - 9:15 am
YWG
-
PDX
13h 05m
1 stop
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m
1 stop
$389Air Canada
Thu, Mar 26 - Sun, Mar 29
Air Canada Logo
9:15 pm - 9:15 am
YWG
-
PDX
14h 00m
2 stops
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m
1 stop
$405Air Canada
Fri, Feb 13 - Sun, Feb 15
Air Canada Logo
9:50 pm - 9:15 am
YWG
-
PDX
13h 25m
1 stop
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m
1 stop
$407Air Canada
Tue, Feb 24 - Sun, Mar 1
Air Canada Logo
8:00 am - 6:30 pm
YWG
-
PDX
12h 30m
2 stops
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m
1 stop
$418Air Canada
Tue, Feb 24 - Sat, Feb 28
American Airlines Logo
12:10 pm - 10:58 am
YWG
-
PDX
24h 48m
2 stops
American Airlines Logo
9:44 pm - 11:35 pm
PDX
-
YWG
23h 51m
2 stops
$463American Airlines
Sat, Jun 20 - Mon, Jun 22
WestJet Logo
7:00 am - 1:20 pm
YWG
-
PDX
8h 20m
2 stops
WestJet Logo
2:00 pm - 11:40 am
PDX
-
YWG
19h 40m
1 stop
$466WestJet
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 January and June, when the average cost of round-trip tickets is $472 and $431 respectively.

How far in advance should I book a flight from Winnipeg to Oregon?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Winnipeg to Oregon, you should book around 3 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$203
Best time to beat the crowds with an average 2% drop in price.
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 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 10637 reviews
6.3Food
7.3Boarding
7.8Crew
7.1Comfort
6.8Entertainment
Airline reviews

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.

2.0 MediocreAnonymous, Jan 2026
YUL - DFW
Read more Air Canada reviews

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.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

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

Information on your arrival and departure airports