$209 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 7/23. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% 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
Portland2 stops$307
Medford
Medford2 stops$638
Portland
Portland2 stops$307
Medford
Medford2 stops$638

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, Aug 14 - Mon, Aug 24
WestJet Logo
7:00 am - 1:50 pm
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 pm - 10:10 pm
PDX
-
YWG
5h 40m
1 stop
$307WestJet
Fri, Aug 14 - Mon, Aug 24
WestJet Logo
10:10 am - 1:50 pm
YWG
-
PDX
5h 40m
1 stop
WestJet Logo
2:30 pm - 10:10 pm
PDX
-
YWG
5h 40m
1 stop
$309WestJet
Wed, Jun 24 - Wed, Jul 15
Air Canada Logo
5:30 am - 9:31 am
YWG
-
PDX
6h 01m
1 stop
Air Canada Logo
7:45 pm - 3:02 am
PDX
-
YWG
5h 17m
1 stop
$317Air Canada
Fri, Aug 14 - Mon, Aug 24
WestJet Logo
7:00 am - 1:50 pm
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 pm - 12:00 pm
PDX
-
YWG
19h 30m
2 stops
$321WestJet
Sat, Jul 4 - Sat, Jul 11
WestJet Logo
10:10 am - 1:50 pm
YWG
-
PDX
5h 40m
1 stop
WestJet Logo
2:30 pm - 10:10 pm
PDX
-
YWG
5h 40m
1 stop
$324WestJet
Tue, Jun 30 - Mon, Jul 13
WestJet Logo
4:15 pm - 1:50 pm
YWG
-
PDX
23h 35m
2 stops
WestJet Logo
2:30 pm - 2:40 pm
PDX
-
YWG
22h 10m
2 stops
$330WestJet
Tue, Oct 13 - Fri, Oct 16
Delta Logo
12:30 pm - 11:12 pm
YWG
-
MFR
12h 42m
2 stops
Delta Logo
12:25 pm - 11:50 am
MFR
-
YWG
21h 25m
2 stops
$638Delta
Tue, Oct 13 - Fri, Oct 16
Delta Logo
12:30 pm - 11:12 pm
YWG
-
MFR
12h 42m
2 stops
Delta Logo
12:25 pm - 11:50 am
MFR
-
YWG
21h 25m
2 stops
$640Delta
Tue, Oct 13 - Fri, Oct 16
United Airlines Logo
8:30 am - 10:59 pm
YWG
-
MFR
16h 29m
2 stops
United Airlines Logo
5:00 am - 8:48 pm
MFR
-
YWG
13h 48m
1 stop
$646United Airlines
Tue, Oct 13 - Fri, Oct 16
United Airlines Logo
8:30 am - 9:14 pm
YWG
-
MFR
14h 44m
1 stop
United Airlines Logo
5:00 am - 8:48 pm
MFR
-
YWG
13h 48m
1 stop
$673United Airlines
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Winnipeg to Oregon departing in August.

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 $122 (return) on average. On the other hand, the most expensive months are January and February, when the average cost of round-trip tickets is $345 and $342 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$209
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 18% 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 11129 reviews
6.8Entertainment
7.8Crew
6.3Food
7.3Boarding
7.1Comfort
Airline reviews

It was a nice and smooth trip. Gave a friendly environment throughout the journey.

10.0 ExcellentSivayogan. Dr, Jun 2026
YYZ - RDU
Read more Air Canada reviews

It was a nice and smooth trip. Gave a friendly environment throughout the journey.

Meal and drink service was good. Old plane with old business class seats were quite disappointing

The flight was smooth, the plane was spacious and clean, the staff was kind and the food was decent.

Pretzels were a bit dry and dusty, however it is nice to have a choice between sweet and savory snacks.

Flight crew was great, and even the crew for checking bags! I had a question for a friend of mine flying tomorrow and the man I talked to was awesome and answered my questions and looked up things for me when he didn’t have to! I was able to give her current & accurate info for her flight and she was so appreciative too!!

Never flown with Air Canada before, but it's now a top choice! Loved it!

Horrible crew, horrible seats configuration, ridiculous space in the toilets, Air Canada is no longer a option.

Crew at gate and onboard were just very OK, not very friendly and honestly seemed bothered to be there. I will give a shout out to still selling headphones for those who forgot.

Flight Boarded and departed on time. The Flight crew was very friendly and accommodating. The aircraft was clean and free from clutter and debris. I will be happy to recommend Air Canada to my friends and relatives for their flight needs. They were very attentive and responsive to our needs as Senior citizens.

Another good flight experience with Air Canada. The business section did not feature the full length sleeping arrangement, but this was a shorter trip. The food was excellent. But the flight crew was truly top tier: friendly, cheerful, helpful at all the right times. Air Canada truly outshines all U.S. carriers.

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

Information on your arrival and departure airports

Winnipeg (YWG)