YWG - PDX

$163 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 5/30. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$272
Typical prices: $457-$369
WestJet
Wed 9/30Wed 10/7
YWG - PDX • 1 stop
Cheapest one-way
$163
Typical prices: $341-$353
WestJet
Sat 5/30
YWG - PDX • 1 stop
Top airlines
WestJet
Cheapest • from $272 (round-trip)
Air Canada
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop 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
Calgary (YYC)
Cheapest • Avg $308 (round-trip)
Calgary (YYC)
Shortest trip • 6h 35m (one-way)
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 35% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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!
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

Wed, Sep 30 - Wed, Oct 7
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
$272WestJet
Wed, Sep 30 - Wed, Oct 7
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
$277WestJet
Tue, Oct 20 - Sat, Oct 24
Air Canada Logo
5:45 am - 9:31 am
YWG
-
PDX
5h 46m
1 stop
Air Canada Logo
10:10 am - 5:47 pm
PDX
-
YWG
5h 37m
1 stop
$284Air Canada
Mon, Sep 28 - Fri, Oct 2
Delta Logo
6:40 am - 10:51 am
YWG
-
PDX
6h 11m
1 stop
Delta Logo
12:40 am - 11:34 am
PDX
-
YWG
8h 54m
1 stop
$286Delta
Tue, Oct 20 - Sat, Oct 24
United Airlines Logo
8:30 am - 10:52 pm
YWG
-
PDX
16h 22m
1 stop
United Airlines Logo
10:43 am - 8:48 pm
PDX
-
YWG
8h 05m
1 stop
$290United Airlines
Wed, Sep 23 - Sat, Sep 26
United Airlines Logo
7:00 am - 6:47 pm
YWG
-
PDX
13h 47m
1 stop
United Airlines Logo
8:30 am - 10:24 pm
PDX
-
YWG
11h 54m
1 stop
$291United Airlines
Wed, Sep 30 - Mon, Oct 5
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
$306WestJet
Fri, Jul 10 - Sat, Jul 11
Delta Logo
3:59 pm - 11:18 pm
YWG
-
PDX
9h 19m
1 stop
Delta Logo
12:33 am - 11:53 am
PDX
-
YWG
9h 20m
1 stop
$307Delta
Fri, Aug 14 - Mon, Aug 24
Air Canada Logo
5:40 am - 9:31 am
YWG
-
PDX
5h 51m
1 stop
Air Canada Logo
7:45 pm - 1:10 pm
PDX
-
YWG
15h 25m
1 stop
$308Air Canada
Fri, Aug 14 - Mon, Aug 24
Air Canada Logo
5:40 am - 9:31 am
YWG
-
PDX
5h 51m
1 stop
Air Canada Logo
3:30 pm - 2:57 am
PDX
-
YWG
9h 27m
1 stop
$310Air Canada
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 September.

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 $261 (return) on average. On the other hand, the most expensive months are March and February, where the average cost of round-trip tickets is $572 and $503 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$163
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 31% 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 $163 for a one-way ticket and $272 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 is the only airline alliance operating flights between Winnipeg and Portland.

  • 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 11017 reviews
7.1Comfort
7.8Crew
6.8Entertainment
6.3Food
7.3Boarding
Airline reviews

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.

10.0 ExcellentDana, May 2026
YUL - DEN
Read more Air Canada reviews

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.

Flight operated by PAL. We boarded, and one engine started. The crew found some problem that could not be fixed. The flight was canceled. This run from yhz-bos is very unreliable.

Everything. The crew was so friendly, helpful & smiled. We had an excellent flight getting in earlier.

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.

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

Information on your arrival and departure airports

Winnipeg (YWG)
Portland (PDX)