YWG - PDX

C$ 263 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 11/3. 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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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

Wed, 4 Mar - Thu, 5 Mar
Air Canada Logo
8:00 a.m. - 2:40 p.m.YWG-PDX
8h 40m2 stops
Air Canada Logo
3:15 p.m. - 1:09 a.m.PDX-YWG
7h 54m1 stop
C$ 480Air Canada
Find Deal
Wed, 4 Mar - Thu, 5 Mar
Air Canada Logo
10:45 a.m. - 2:40 p.m.YWG-PDX
5h 55m1 stop
Air Canada Logo
9:50 a.m. - 6:09 p.m.PDX-YWG
6h 19m1 stop
C$ 481Air Canada
Find Deal
Wed, 24 Dec - Sun, 28 Dec
Air Canada Logo
9:40 p.m. - 9:15 a.m.YWG-PDX
13h 35m1 stop
Air Canada Logo
3:15 p.m. - 1:14 a.m.PDX-YWG
7h 59m1 stop
C$ 523Air Canada
Find Deal
Wed, 4 Mar - Thu, 5 Mar
United Airlines Logo
2:20 p.m. - 12:44 a.m.YWG-PDX
12h 24m2 stops
United Airlines Logo
1:25 p.m. - 11:39 a.m.PDX-YWG
20h 14m2 stops
C$ 655United Airlines
Find Deal
Thu, 18 Dec - Thu, 1 Jan
WestJet Logo
2:40 p.m. - 6:50 p.m.YWG-PDX
30h 10m2 stops
WestJet Logo
2:11 p.m. - 6:06 p.m.PDX-YWG
25h 55m2 stops
C$ 700WestJet
Find Deal
Wed, 24 Dec - Sun, 28 Dec
WestJet Logo
6:45 a.m. - 11:05 a.m.YWG-PDX
30h 20m2 stops
WestJet Logo
12:29 p.m. - 10:41 p.m.PDX-YWG
8h 12m2 stops
C$ 701WestJet
Find Deal
Sun, 21 Dec - Sun, 28 Dec
Delta Logo
6:40 a.m. - 6:50 p.m.YWG-PDX
14h 10m2 stops
Delta Logo
12:16 p.m. - 11:44 p.m.PDX-YWG
9h 28m1 stop
C$ 1,003Delta
Find Deal
Sun, 21 Dec - Sun, 28 Dec
Delta Logo
12:35 p.m. - 8:34 p.m.YWG-PDX
9h 59m1 stop
Delta Logo
12:16 p.m. - 11:44 p.m.PDX-YWG
9h 28m1 stop
C$ 1,076Delta
Find Deal
Thu, 18 Dec - Thu, 1 Jan
American Airlines Logo
6:00 a.m. - 9:24 p.m.YWG-PDX
17h 24m3 stops
American Airlines Logo
10:21 p.m. - 11:35 p.m.PDX-YWG
23h 14m2 stops
C$ 1,525American Airlines
Find Deal
Thu, 18 Dec - Thu, 1 Jan
American Airlines Logo
6:00 a.m. - 9:24 p.m.YWG-PDX
17h 24m3 stops
American Airlines Logo
10:21 p.m. - 11:35 p.m.PDX-YWG
23h 14m2 stops
C$ 1,527American Airlines
Find Deal

Everything you should know

Top airlines
Air Canada
Cheapest • from C$ 480 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
July
Cheapest • 23% price drop
February
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 480
Overall average: C$ 565
Air Canada
Wed 4/3Thu 5/3
YWG - PDX • 2 stops
Cheapest one-way flights
C$ 260
Typical prices: C$ 288-C$ 318
Multiple Airlines
Wed 11/3
YWG - PDX • 1 stop
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
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 March.

What’s the cheapest day of the week to fly from Winnipeg to Portland?

The average price of all round-trip flights from Winnipeg to Portland clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Portland on a Sunday and more expensive on a Monday. On your return trip to Winnipeg, you should consider flying back on a Thursday, and avoid Fridays for better deals.

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 July, where tickets cost C$ 376 (return) on average. On the other hand, the most expensive months are June and January, where the average cost of round-trip tickets is C$ 600 and C$ 588 respectively.

Good to know

Low seasonSeptember
Cheapest flightC$ 260
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly and prices are also 15% 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$ 260 for a one-way ticket and C$ 480 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, United Airlines or WestJet?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Portland are United Airlines and WestJet. With an average price for the route of C$ 426 and an overall rating of 7.4, United Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of C$ 447 and an overall rating of 7.2.

  • 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 3 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.
7.4
United AirlinesOverall score based on 9002 reviews
6.6Food
8.1Crew
7.1Entertainment
7.7Boarding
7.3Comfort
Airline reviews

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

4.0 OkayAnonymous, Oct 2025YVR - SFO
Read more United Airlines reviews

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Do not fly on WestJet if you have a connection. It failed to integrate with my connecting Delta flight and I almost missed it.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

A little better seat cushions would be appreciated. Crews were all good.

The process and flight were both smooth and trouble free

Flight delayed 3 hours, missed my connection in Atlanta. Instead of getting to Savannah at 6PM arrived after 10:00PM Middle seat, couldn't get isle or window, couldn't book my seats in advance, had to book at the gate. That's a 1st for me and I used to travel a lot

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

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 Portland

Information on your arrival and departure airports

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