YWG - PDX

C$ 223 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 30/10. 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 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

Tue, 7 Oct - Tue, 14 Oct
Air Canada Logo
5:05 a.m. - 9:20 a.m.YWG-PDX
6h 15m1 stop
Air Canada Logo
3:25 p.m. - 2:02 a.m.PDX-YWG
8h 37m1 stop
C$ 325Air Canada
Find Deal
Tue, 7 Oct - Tue, 14 Oct
Delta Logo
12:20 p.m. - 8:26 p.m.YWG-PDX
10h 06m1 stop
Delta Logo
7:59 p.m. - 11:30 a.m.PDX-YWG
13h 31m2 stops
C$ 332Delta
Find Deal
Tue, 7 Oct - Tue, 14 Oct
Air Canada Logo
6:15 a.m. - 11:01 p.m.YWG-PDX
18h 46m2 stops
Air Canada Logo
3:25 p.m. - 11:08 a.m.PDX-YWG
17h 43m2 stops
C$ 362Air Canada
Find Deal
Tue, 4 Nov - Tue, 11 Nov
Air Canada Logo
10:45 a.m. - 2:45 p.m.YWG-PDX
6h 00m1 stop
Air Canada Logo
3:15 p.m. - 1:09 a.m.PDX-YWG
7h 54m1 stop
C$ 413Air Canada
Find Deal
Thu, 6 Nov - Sat, 8 Nov
United Airlines Logo
2:20 p.m. - 9:38 a.m.YWG-PDX
21h 18m2 stops
United Airlines Logo
10:05 a.m. - 11:57 a.m.PDX-YWG
23h 52m2 stops
C$ 436United Airlines
Find Deal
Mon, 3 Nov - Sun, 9 Nov
Air Canada Logo
6:00 a.m. - 6:30 p.m.YWG-PDX
14h 30m1 stop
Air Canada Logo
3:15 p.m. - 1:09 a.m.PDX-YWG
7h 54m1 stop
C$ 437Air Canada
Find Deal
Thu, 6 Nov - Fri, 7 Nov
United Airlines Logo
2:20 p.m. - 9:38 a.m.YWG-PDX
21h 18m2 stops
United Airlines Logo
3:54 p.m. - 8:56 p.m.PDX-YWG
27h 02m2 stops
C$ 505United Airlines
Find Deal
Fri, 7 Nov - Thu, 13 Nov
WestJet Logo
6:45 a.m. - 12:50 p.m.YWG-PDX
32h 05m2 stops
WestJet Logo
12:35 a.m. - 8:06 p.m.PDX-YWG
17h 31m2 stops
C$ 675WestJet
Find Deal
Tue, 7 Oct - Mon, 13 Oct
WestJet Logo
8:30 a.m. - 10:40 p.m.YWG-PDX
16h 10m2 stops
WestJet Logo
12:40 a.m. - 9:25 p.m.PDX-YWG
18h 45m2 stops
C$ 677WestJet
Find Deal
Fri, 7 Nov - Thu, 13 Nov
Multiple Airlines Logo
4:55 p.m. - 9:40 a.m.YWG-PDX
18h 45m1 stop
Multiple Airlines Logo
12:35 a.m. - 11:36 p.m.PDX-YWG
21h 01m1 stop
C$ 977Multiple Airlines
Find Deal

Everything you should know

Top airlines
Air Canada
Cheapest • from C$ 325 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travellers who book at least 3 weeks in advance save around 56% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 21% price drop
February
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 325
Typical prices: C$ 343-539
Air Canada
Tue 7/10Tue 14/10
YWG - PDX • 1 stop
Cheapest one-way flights
C$ 223
Typical prices: C$ 228-622
Multiple Airlines
Thu 30/10
YWG - PDX • 2 stops
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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?

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$ 370 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is C$ 590 and C$ 556 respectively.

How far in advance should I book a flight from Winnipeg to Portland?

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 Portland, 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 Portland, 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.

Good to know

Low seasonJanuary
Cheapest flightC$ 223
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

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$ 162 for a one-way ticket and C$ 236 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, and SkyTeam are the airline alliances operating flights between Winnipeg and Portland, with Star Alliance being the most commonly used for this route.

  • 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$ 408 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$ 439 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 8924 reviews
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
Airline reviews

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

10.0 ExcellentPaulos, Aug 2025YUL - IAD
Read more United Airlines reviews

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.

Very nice and clean plane. Transit time between flights was tight though

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

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.

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 Portland

Information on your arrival and departure airports

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