YWG - PDX

$157 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 5/31. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$302
Typical prices: $288-$453
WestJet
Mon 5/18Sat 5/23
YWG - PDX • 1 stop
Cheapest one-way
$157
Typical prices: $152-$343
WestJet
Sun 5/31
YWG - PDX • 1 stop
Top airlines
WestJet
Cheapest • from $302 (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 50% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 29% price drop
February
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Mon, May 18 - Sat, May 23
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
$302WestJet
Mon, May 18 - Sat, May 23
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
$303WestJet
Tue, May 19 - Sun, May 24
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
$304WestJet
Tue, May 19 - Sun, May 24
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
$305WestJet
Mon, May 18 - Sat, May 23
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
$318WestJet
Mon, May 18 - Sun, May 24
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
$328WestJet
Mon, May 18 - Sat, May 23
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
$330WestJet
Mon, Jun 1 - Sat, Jun 6
WestJet Logo
10:15 pm - 1:50 pm
YWG
-
PDX
17h 35m
2 stops
WestJet Logo
2:30 pm - 10:10 pm
PDX
-
YWG
5h 40m
1 stop
$331WestJet
Tue, May 19 - Sun, May 24
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
$332WestJet
Mon, May 18 - Sat, May 23
WestJet Logo
7:00 am - 1:50 pm
YWG
-
PDX
8h 50m
2 stops
WestJet Logo
2:30 pm - 12:15 pm
PDX
-
YWG
19h 45m
1 stop
$338WestJet
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 May.

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 January and June, where the average cost of round-trip tickets is $630 and $431 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 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Find deals

Good to know

Low seasonNovember
Cheapest flight$157
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 18% 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 $157 for a one-way ticket and $302 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 10694 reviews
7.1Comfort
7.8Crew
6.3Food
6.8Entertainment
7.3Boarding
Airline reviews

This is a great non-stop YVR-MIA. Very comfortable plane, and no transfer through a city that gets major winter weather!

10.0 ExcellentBrian, Feb 2026
YVR - MIA
Read more Air Canada reviews

This is a great non-stop YVR-MIA. Very comfortable plane, and no transfer through a city that gets major winter weather!

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

Air Canada’s problems are not staff related by and large, no. The problem is tiny jets between the U.S. and Canada - yes, believe it or not they are still “international” (just ask our own Mango Maniac in power in the U.S.). The little aisle is compounded by a design flaw of a “dog leg” starting at seat 12. Woe be unto you if you sit here as passengers and attendants do not have sufficient room to not hit you in the face with backpacks. One thing I will say very positively about Air Canada is you still provide pillows and blankets on transcontinental flights to all, not just the elites. Your tiny improperly designed jets are also a problem flying city to city within Canada also. One can only say you remind us of a “Jet Blue” or “Spirit” experience. Also your luggage space is downright Byzantine! We will endeavor to avoid you and use other U.S. carriers, albeit charging more.

Terrible canceled flight and lost my luggage. Flew me to Halifax. Tgat flight was delayed, had to spend night in airport chair.

My seat was not comfortable. Flight was smooth. Regretfully we had two delays before takeoff

Amazing service, with enthusiastic crew members, and some breathtaking views of Vancouver. No IFE though, as it is only a 1 hour flight on a regional Turboprop jet.

I like the fact air Canada is on time The food you guys serve is not good

They are very proactive and made our boarding easy and always notified us about any changes well in advance.

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

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

Information on your arrival and departure airports

Winnipeg (YWG)
Portland (PDX)