$162 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 10/30. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$236
Portland
Portland1 stop$236

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

Tue, Oct 7 - Tue, Oct 14
Air Canada Logo
5:05 am - 9:20 amYWG-PDX
6h 15m1 stop
Air Canada Logo
3:25 pm - 2:02 amPDX-YWG
8h 37m1 stop
$236Air Canada
Find Deal
Tue, Oct 7 - Tue, Oct 14
Delta Logo
12:20 pm - 8:26 pmYWG-PDX
10h 06m1 stop
Delta Logo
7:59 pm - 11:30 amPDX-YWG
13h 31m2 stops
$241Delta
Find Deal
Tue, Oct 7 - Tue, Oct 14
Air Canada Logo
6:15 am - 11:01 pmYWG-PDX
18h 46m2 stops
Air Canada Logo
3:25 pm - 11:08 amPDX-YWG
17h 43m2 stops
$263Air Canada
Find Deal
Tue, Nov 4 - Mon, Nov 10
Air Canada Logo
10:45 am - 2:45 pmYWG-PDX
6h 00m1 stop
Air Canada Logo
3:15 pm - 1:09 amPDX-YWG
7h 54m1 stop
$300Air Canada
Find Deal
Wed, Mar 4 - Thu, Mar 5
Air Canada Logo
10:45 am - 2:45 pmYWG-PDX
6h 00m1 stop
Air Canada Logo
9:50 am - 6:09 pmPDX-YWG
6h 19m1 stop
$311Air Canada
Find Deal
Thu, Nov 6 - Sat, Nov 8
United Airlines Logo
2:20 pm - 9:38 amYWG-PDX
21h 18m2 stops
United Airlines Logo
10:05 am - 11:57 amPDX-YWG
23h 52m2 stops
$317United Airlines
Find Deal
Wed, Mar 4 - Thu, Mar 5
United Airlines Logo
2:20 pm - 10:08 pmYWG-PDX
9h 48m1 stop
United Airlines Logo
3:41 pm - 11:39 amPDX-YWG
17h 58m2 stops
$319United Airlines
Find Deal
Tue, Nov 4 - Sat, Nov 8
Delta Logo
5:40 pm - 8:36 amYWG-PDX
16h 56m2 stops
Delta Logo
1:55 pm - 11:27 pmPDX-YWG
7h 32m1 stop
$321Delta
Find Deal
Fri, Nov 7 - Thu, Nov 13
WestJet Logo
6:45 am - 12:50 pmYWG-PDX
32h 05m2 stops
WestJet Logo
12:35 am - 8:06 pmPDX-YWG
17h 31m2 stops
$491WestJet
Find Deal
Tue, Oct 7 - Mon, Oct 13
WestJet Logo
6:40 am - 11:01 amYWG-PDX
6h 21m1 stop
WestJet Logo
12:40 am - 7:23 pmPDX-YWG
16h 43m2 stops
$492WestJet
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.

How much is a round-trip flight from Winnipeg to Oregon?

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 March, when the average cost of round-trip tickets is $429 and $404 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.

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 56% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$162
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 13% 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 10000 reviews
7.3Boarding
7.1Comfort
7.8Crew
6.8Entertainment
6.3Food
Airline reviews

A sandwich and a drink would have been better thank a snack bar...

8.0 ExcellentShamela, Sep 2025YYZ - JFK
Read more Air Canada reviews

A sandwich and a drink would have been better thank a snack bar...

I liked the behaviour of the crew members.The flight was good.

1 hour late No hot drinks No restroom in the back of the plane

I swear airplane seats keep getting smaller and smaller but everything else was great. Smooth sailing and we got in early.

No food to provide, they forgot that, in some cases, people stay at the airport for hours without food. Now, to provide them with food, they have to ask them to pay, because some don't have money. That way, they can't eat.

After a long flight from Tokyo, our connecting flight home was canceled due to “maintenance” while we were on our layover in Toronto. Very frustrating to close out our honeymoon, although I’m sure others had it even worse during last week’s strike. Air Canada staff at Pearson Airport are the one thing that kept me remotely at peace during this — they were very helpful and deserve a lot of props. But I would not fly Air Canada again.

I had wonderful wheelchair assistance through the Montreal airport onto the flight. Air Canada was excellent in this both at the Fredericton airport and the Montreal one where an attendant helped us through customs as well as transport and baggage security.

Horrible flight cancelled had to buy another very expensive ticket

Flight was cancelled last minute due to Air Canada strike leaving us stranded and having to stressfully find a way home that cost hundreds of dollars in excess cost added to the trip. Having just experienced our mother's funeral service, this was not a good way to end our trip.

Air Canada marooned me in Canada with no way back home during my summer vacation. I had to buy a last minute flight ticket for over $500 to make it back home. I have their credit card and have flown them for years. Never again.

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

Information on your arrival and departure airports

Winnipeg (YWG)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.