$171 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 12/11. 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, 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$325
Medford
Medford2 stops$538
Portland
Portland1 stop$325
Medford
Medford2 stops$538

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

Wed, Dec 10 - Wed, Dec 17
Multiple Airlines Logo
4:55 pm - 10:19 amYWG-PDX
19h 24m1 stop
Multiple Airlines Logo
2:36 pm - 12:43 amPDX-YWG
8h 07m1 stop
$325Multiple Airlines
Find Deal
Wed, Dec 10 - Wed, Dec 17
Multiple Airlines Logo
4:55 pm - 10:19 amYWG-PDX
19h 24m1 stop
Multiple Airlines Logo
2:36 pm - 12:39 amPDX-YWG
32h 03m2 stops
$333Multiple Airlines
Find Deal
Thu, Dec 11 - Thu, Dec 18
Air Canada Logo
10:45 am - 2:40 pmYWG-PDX
5h 55m1 stop
Air Canada Logo
3:15 pm - 1:14 amPDX-YWG
7h 59m1 stop
$336Air Canada
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Wed, Dec 10 - Wed, Dec 17
Delta Logo
6:40 am - 3:33 pmYWG-PDX
10h 53m2 stops
Delta Logo
7:30 pm - 11:45 amPDX-YWG
14h 15m2 stops
$340Delta
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Wed, Mar 4 - Thu, Mar 5
Air Canada Logo
8:00 am - 2:40 pmYWG-PDX
8h 40m2 stops
Air Canada Logo
3:15 pm - 1:09 amPDX-YWG
7h 54m1 stop
$343Air Canada
Find Deal
Wed, Dec 10 - Tue, Dec 16
Delta Logo
6:40 am - 3:33 pmYWG-PDX
10h 53m2 stops
Delta Logo
12:32 am - 11:45 amPDX-YWG
9h 13m1 stop
$344Delta
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Thu, Dec 18 - Thu, Jan 1
WestJet Logo
6:45 am - 5:43 pmYWG-PDX
12h 58m2 stops
WestJet Logo
2:11 pm - 8:06 pmPDX-YWG
27h 55m2 stops
$500WestJet
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Thu, Dec 18 - Thu, Jan 1
WestJet Logo
10:55 am - 5:43 pmYWG-PDX
32h 48m2 stops
WestJet Logo
2:11 pm - 8:06 pmPDX-YWG
27h 55m2 stops
$501WestJet
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Wed, Dec 10 - Wed, Dec 17
United Airlines Logo
2:20 pm - 11:03 amYWG-PDX
22h 43m3 stops
United Airlines Logo
1:14 pm - 11:57 amPDX-YWG
20h 43m2 stops
$542United Airlines
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Wed, Apr 15 - Sun, Apr 19
United Airlines Logo
8:30 am - 1:09 pmYWG-MFR
6h 39m1 stop
United Airlines Logo
6:35 pm - 8:48 pmMFR-YWG
24h 13m2 stops
$586United Airlines
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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 $269 (return) on average. On the other hand, the most expensive months are June and January, when the average cost of round-trip tickets is $429 and $420 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.

If your flying dates are flexible, you should consider flying to Oregon on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Winnipeg to Oregon. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

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Good to know

Low seasonSeptember
Cheapest flight$171
Best time to beat the crowds with an average 6% 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.

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

    The cheapest time of day to fly to Oregon is generally in the evening, when round-trip flights cost $297 on average. Morning departures are around 2% 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 $305.

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 10371 reviews
7.3Boarding
7.1Comfort
7.8Crew
6.8Entertainment
6.3Food
Airline reviews

The free Wi-fi for Aeroplan members was a great touch. The time passed quickly. I found the seats seemed a little closer together than I remember. Not Air Canada's fault, but we were about 20 minutes late landing because the airport was too busy. We had to circle around for a while. The boarding and disembarking went very smoothly.

8.0 ExcellentAnonymous, Oct 2025YYZ - SFO
Read more Air Canada reviews

The free Wi-fi for Aeroplan members was a great touch. The time passed quickly. I found the seats seemed a little closer together than I remember. Not Air Canada's fault, but we were about 20 minutes late landing because the airport was too busy. We had to circle around for a while. The boarding and disembarking went very smoothly.

It was crazy, boarded over a hour late from scheduled departure. Then when arrived in BNA issued with getting off the plane…over 1/2 hour. Not looking forward to flying Air Canada, ever again.

Extremely turbulent landing. Crew was friendly and plane comfortable. Airport and US pre clearance was understaffed

The airplane is way too tight, you can hardly enter into your row to sit.. more like kids seats than adults.

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.

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

Information on your arrival and departure airports

Winnipeg (YWG)

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