YWG - PDX

$127 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 10/4. 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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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, Oct 24 - Mon, Oct 27
Air Canada Logo
7:10 pm - 11:01 pmYWG-PDX
5h 51m1 stop
Air Canada Logo
3:15 pm - 1:09 amPDX-YWG
7h 54m1 stop
$243Air Canada
Find Deal
Fri, Oct 24 - Mon, Oct 27
Air Canada Logo
5:05 am - 9:20 amYWG-PDX
6h 15m1 stop
Air Canada Logo
3:15 pm - 1:09 amPDX-YWG
7h 54m1 stop
$258Air Canada
Find Deal
Fri, Oct 24 - Mon, Oct 27
Air Canada Logo
6:15 am - 11:01 pmYWG-PDX
18h 46m2 stops
Air Canada Logo
3:15 pm - 1:09 amPDX-YWG
7h 54m1 stop
$267Air Canada
Find Deal
Fri, Oct 24 - Mon, Oct 27
Multiple Airlines Logo
4:25 pm - 12:28 amYWG-PDX
10h 03m2 stops
Multiple Airlines Logo
3:15 pm - 1:09 amPDX-YWG
7h 54m1 stop
$290Multiple Airlines
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
Thu, Nov 6 - Mon, Nov 10
United Airlines Logo
2:20 pm - 9:38 amYWG-PDX
21h 18m2 stops
United Airlines Logo
11:59 pm - 11:57 amPDX-YWG
9h 58m1 stop
$317United 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
Wed, Dec 17 - Fri, Jan 2
United Airlines Logo
2:20 pm - 10:00 amYWG-PDX
21h 40m2 stops
United Airlines Logo
5:00 am - 8:51 pmPDX-YWG
13h 51m1 stop
$335United Airlines
Find Deal
Mon, Nov 3 - Sat, Nov 8
Delta Logo
5:40 pm - 8:36 amYWG-PDX
16h 56m2 stops
Delta Logo
5:25 pm - 11:48 amPDX-YWG
16h 23m2 stops
$356Delta
Find Deal
Fri, Oct 24 - Mon, Oct 27
Multiple Airlines Logo
7:00 am - 12:28 amYWG-PDX
19h 28m2 stops
Multiple Airlines Logo
9:50 am - 12:03 amPDX-YWG
12h 13m2 stops
$426Multiple Airlines
Find Deal

Everything you should know

Top airlines
Air Canada
Cheapest • from $243 (round-trip)
Air Canada
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travelers 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
$243
Overall average: $346
Air Canada
Fri 10/24Mon 10/27
YWG - PDX • 1 stop
Cheapest one-way
$127
Typical prices: $166-452
Air Canada
Sat 10/4
YWG - PDX • 1 stop
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KAYAK searches 100s 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.

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 Thursday and more expensive on a Saturday. On your return trip to Winnipeg, you should consider flying back on a Friday, and avoid Sundays 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 $269 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is $429 and $404 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 flight$127
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 $127 for a one-way ticket and $243 for a round-trip.

  • Do I need a passport to fly between Winnipeg and Portland?

    Yes

  • Which airports will I be using when flying from Winnipeg to Portland?

    On your way to Portland, you’ll fly out from Winnipeg. You’ll be landing at Portland.

  • 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.

  • 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. Booking your flights between Winnipeg and PDX can sometimes prove cheaper using this method.

  • 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 airline 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.
7.1
Air CanadaOverall score based on 10000 reviews
7.1Comfort
6.3Food
7.8Crew
7.3Boarding
6.8Entertainment
Airline reviews

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

8.0 ExcellentAnonymous, Sep 2025YYZ - SFO
Read more Air Canada reviews

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.

Flight was cancelled last minute. Had to scramble and purchase a $2000 flight through a separate airlines. Stuck in Toronto two extra days. Missed my first two days on a new job. Had to rent a car for an additional two days. Scrambled to fins a place to live those extra two days. Spent a ton of extra money and lost a lot of money, as well as made a poor impression at work. Difficult difficult difficult

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

Information on your arrival and departure airports

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