$190 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 12/25. 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$288
Medford
Medford1 stop$583
Portland
Portland2 stops$288
Medford
Medford1 stop$583

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

Fri, Jan 9 - Sun, Jan 11
Multiple Airlines Logo
6:15 am - 5:27 pmYWG-PDX
13h 12m2 stops
Multiple Airlines Logo
11:45 am - 12:43 amPDX-YWG
10h 58m1 stop
$288Multiple Airlines
Find Deal
Fri, Jan 9 - Sun, Jan 11
Multiple Airlines Logo
5:05 pm - 9:37 amYWG-PDX
18h 32m1 stop
Multiple Airlines Logo
11:45 am - 12:43 amPDX-YWG
10h 58m1 stop
$310Multiple Airlines
Find Deal
Wed, Mar 4 - Thu, Mar 5
Air Canada Logo
10:40 am - 2:40 pmYWG-PDX
6h 00m1 stop
Air Canada Logo
3:15 pm - 1:14 amPDX-YWG
7h 59m1 stop
$342Air Canada
Find Deal
Wed, Mar 4 - Thu, Mar 5
Air Canada Logo
10:40 am - 2:40 pmYWG-PDX
6h 00m1 stop
Air Canada Logo
3:15 pm - 1:14 amPDX-YWG
7h 59m1 stop
$343Air Canada
Find Deal
Fri, Jan 9 - Sun, Jan 11
United Airlines Logo
2:20 pm - 12:31 amYWG-PDX
12h 11m2 stops
United Airlines Logo
7:51 pm - 11:57 amPDX-YWG
14h 06m2 stops
$397United Airlines
Find Deal
Sat, Nov 22 - Fri, Nov 28
WestJet Logo
5:49 pm - 11:14 amYWG-PDX
19h 25m1 stop
WestJet Logo
12:35 am - 11:48 amPDX-YWG
9h 13m1 stop
$499WestJet
Find Deal
Thu, Dec 18 - Thu, Jan 1
WestJet Logo
6:45 am - 5:43 pmYWG-PDX
12h 58m2 stops
WestJet Logo
12:16 pm - 7:12 pmPDX-YWG
28h 56m2 stops
$504WestJet
Find Deal
Wed, Apr 15 - Sun, Apr 19
United Airlines Logo
8:45 am - 9:26 pmYWG-MFR
14h 41m1 stop
United Airlines Logo
5:00 am - 8:52 pmMFR-YWG
13h 52m1 stop
$583United Airlines
Find Deal
Fri, Jan 9 - Sun, Jan 11
American Airlines Logo
12:10 pm - 1:41 pmYWG-PDX
27h 31m3 stops
American Airlines Logo
6:00 am - 11:35 pmPDX-YWG
15h 35m2 stops
$589American Airlines
Find Deal
Thu, Dec 18 - Thu, Jan 1
American Airlines Logo
6:00 am - 9:24 pmYWG-PDX
17h 24m3 stops
American Airlines Logo
10:21 pm - 11:35 pmPDX-YWG
23h 14m2 stops
$976American Airlines
Find Deal
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 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.

Good to know

Low seasonNovember
Cheapest flight$190
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.

  • 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 10429 reviews
7.8Crew
6.8Entertainment
7.1Comfort
7.3Boarding
6.3Food
Airline reviews

Air Canada Rouge is great. Toronto Airport is the usual nightmare

10.0 ExcellentCatherine, Nov 2025YYZ - TPA
Read more Air Canada reviews

Air Canada Rouge is great. Toronto Airport is the usual nightmare

Good but need to be better with the flight times.

The staff could not have been any friendlier. Lots of usb ports on our aircraft.

The staff was great and made the long trip easy peasy!

Air Canada cancelled our flight and reschedule it 26 hours later that completely interrupted my family's long waited Japan trip, it wasn't due to natural reason such as weather but under the company's control. On the day we wasted 9 hours of our time from 6am to 3pm, including a few hours in the customer counter waiting for supervisor to handle our rescheduling. When we came to the counter for rebooking help there were at least 4 employees on the counter but we were told they were not trained to handle customer rebooking, we were also told the supervisor could come 10:30 to handle our rebooking, but she showed up more than one hour later, the end result was exactly the same so the few hours we spent waiting for her was completely wasted; We already prepaid hotel and all the tickets for the our stay in Tokyo so all of the cost for the first day is completed wasted; The $80 meal voucher issues was far less than our financial loss due to the financial cancellation, and it was not surprisingly invalid (as Your company screw up everything possible along the flight), the vouchers were supposed to last 72 hours, when we tried to used it at our lounge next day less than 24 hours from its issuing at a designated restaurant, the worker there couldn't scan the vouchers after multiple tries on all 4 vouchers issued, so we had to pay the food from our own money; For the two return flights they were also full of unfortunate events that caused bad experience and further delay and waste of our time, both flights departed late and the last leg had another significant delay of more than half an hour after touchdown, the gate was for some reason not available so we waited more than half an hour, when we got out of plane it was almost one hour later than the supposed arrival time; The gate you arranged is the farthest in Vancouver airport, also was the luggage pickup location in Seattle airport; We also called customer service for rescheduling help and after a long time wait (more than an hour) we got a call back but the CS representative was equally clueless and unhelpful. Other than a fatal crash, your company couldn't do anything right and provided the worst service possible among the tons of flights we have taken in our lives.

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

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

Information on your arrival and departure airports