YWG - PDX

C$ 197 Find Cheap Flights from Winnipeg to Portland

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 Portland departing on 22/6. 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 Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Portland, 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 Portland, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
C$ 311
Typical prices: C$ 625-C$ 416
WestJet
Fri 26/6Fri 3/7
YWG - PDX • 2 stops
Cheapest one-way flights
C$ 197
Typical prices: C$ 167-C$ 270
WestJet
Mon 22/6
YWG - PDX • 1 stop
Top airlines
Cheapest • from C$ 311 (round-trip)
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
Not available
There are currently no direct flights between Winnipeg and Portland. You’ll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg C$ 423 (round-trip)
Shortest trip • 6h 14m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 44% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Winnipeg to Portland (YWG-PDX)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Portland 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 Portland

Fri, 26 Jun - Fri, 3 Jul
WestJet Logo
7:00 a.m. - 1:50 p.m.
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 p.m. - 11:40 p.m.
PDX
-
YWG
7h 10m
1 stop
C$ 311WestJet
Fri, 26 Jun - Fri, 3 Jul
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
WestJet Logo
2:30 p.m. - 11:40 p.m.
PDX
-
YWG
7h 10m
1 stop
C$ 314WestJet
Tue, 26 May - Sat, 30 May
WestJet Logo
7:00 a.m. - 1:50 p.m.
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
C$ 344WestJet
Fri, 26 Jun - Fri, 3 Jul
WestJet Logo
7:00 a.m. - 1:50 p.m.
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 p.m. - 9:40 p.m.
PDX
-
YWG
29h 10m
2 stops
C$ 361WestJet
Thu, 21 May - Mon, 25 May
WestJet Logo
7:00 a.m. - 1:50 p.m.
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 p.m. - 9:20 a.m.
PDX
-
YWG
16h 50m
2 stops
C$ 378WestJet
Thu, 21 May - Mon, 25 May
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
WestJet Logo
2:30 p.m. - 9:20 a.m.
PDX
-
YWG
16h 50m
2 stops
C$ 381WestJet
Thu, 21 May - Mon, 25 May
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
WestJet Logo
2:30 p.m. - 12:55 a.m.
PDX
-
YWG
8h 25m
1 stop
C$ 388WestJet
Thu, 21 May - Mon, 25 May
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
WestJet Logo
2:30 p.m. - 3:25 p.m.
PDX
-
YWG
22h 55m
1 stop
C$ 403WestJet
Wed, 15 Jul - Sun, 19 Jul
Air Canada Logo
5:40 a.m. - 9:31 a.m.
YWG
-
PDX
5h 51m
1 stop
Air Canada Logo
7:45 p.m. - 3:02 a.m.
PDX
-
YWG
5h 17m
1 stop
C$ 410Air Canada
Tue, 26 May - Sat, 30 May
WestJet Logo
7:00 a.m. - 1:50 p.m.
YWG
-
PDX
32h 50m
2 stops
WestJet Logo
2:30 p.m. - 9:20 a.m.
PDX
-
YWG
16h 50m
2 stops
C$ 428WestJet
Booking Insights

KAYAK's insights & trends for Winnipeg to Portland flights

Get data-powered insights and trends into flights from Winnipeg to Portland 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 Portland?

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 Portland departing in June.

What is the cheapest month to fly from Winnipeg to Portland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Portland, 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 Portland is August, where tickets cost C$ 306 (return) on average. On the other hand, the most expensive months are March and February, where the average cost of round-trip tickets is C$ 781 and C$ 687 respectively.

Good to know

Low seasonJanuary
Cheapest flightC$ 197
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly and prices are also 38% lower on average.
Flight from Winnipeg to Portland

When to book flights from Winnipeg to Portland

Are your dates flexible? Find out the best times to travel from Winnipeg to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Winnipeg to Portland

  • What is the cheapest flight from Winnipeg to Portland?

    In the last 3 days, the lowest price for a flight from Winnipeg to Portland was C$ 197 for a one-way ticket and C$ 311 for a round-trip.

  • Which aircraft models fly most regularly from Winnipeg to Portland?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Winnipeg to Portland?

    Star Alliance is the only airline alliance operating flights between Winnipeg and Portland.

  • Which is the best airline for flights from Winnipeg to Portland, WestJet or Air Canada?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Portland are WestJet and Air Canada. With an average price for the route of C$ 501 and an overall rating of 7.2, WestJet is the most popular choice. Air Canada is also a great choice for the route, with an average price of C$ 539 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Winnipeg to Portland?

    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 Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Winnipeg 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 Portland?

    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 to Portland with an airline and back to Winnipeg with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Portland?

    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 to Portland from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Winnipeg to Portland

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to Portland. 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 Portland? 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.
7.2
WestJetOverall score based on 3328 reviews
7.0Comfort
7.9Crew
6.2Food
7.4Boarding
6.1Entertainment
Airline reviews

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

10.0 ExcellentAnonymous, Mar 2026
YLW - SEA
Read more WestJet reviews

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

The window seat on the emergency row was too small. I had a different seat booked and they moved me. My seat remained open. It was very uncomfortable.

Experience was good, the wifi hook up is somewhat tough

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

Overall good experience. The wait for baggage at our destination was quite long, but other than that everything was good as expected

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

Flight and attendance were very good we had 2 hour delay that took the shine of it

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

Be careful about the bad policy and when purchasing seats

Very disappointed with premier lounge. Food selection very poor, both coffee machines out of order. For the price you charge for an upgrade, the seats don’t fully recline, movie selection is old. Not very good value. Asian airlines are light years ahead at a more affordable price.

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

The flight was delayed, but not for weather. We landed over 3hrs later than planned.

The stag were helpful, kind and liked the passengers. The plane was pristinely clean! Great flight!

My flight was delayed more than once, but Air Canada updated us regularly. Friends on other airlines had much worse experiences.

My ticket did not exist when I got to the airport. I had to book another flight and was still charged by Kayak

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

Information on your arrival and departure airports