PDX - YWG

$106 Find Cheap Flights from Portland to Winnipeg

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Winnipeg departing on 8/26. 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 Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Winnipeg, 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 Portland to Winnipeg, 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
$236
Typical prices: $483-$217
WestJet
Fri 8/14Tue 8/25
PDX - YWG • 1 stop
Cheapest one-way
$106
Typical prices: $118-$494
WestJet
Wed 8/26
PDX - YWG • 1 stop
Top airlines
Cheapest • from $236 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Portland and Winnipeg. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $399 (round-trip)
Shortest trip • 6h 01m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 44% price drop
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 Winnipeg!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to Winnipeg (PDX-YWG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Winnipeg 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 Portland to Winnipeg

Fri, Aug 14 - Tue, Aug 25
WestJet Logo
2:30 pm - 11:40 pm
PDX
-
YWG
7h 10m
1 stop
WestJet Logo
7:00 am - 1:50 pm
YWG
-
PDX
8h 50m
2 stops
$236WestJet
Mon, Aug 17 - Wed, Aug 26
WestJet Logo
2:30 pm - 11:40 pm
PDX
-
YWG
7h 10m
1 stop
WestJet Logo
10:10 am - 1:50 pm
YWG
-
PDX
5h 40m
1 stop
$238WestJet
Fri, Aug 14 - Tue, Aug 25
WestJet Logo
2:30 pm - 11:40 pm
PDX
-
YWG
7h 10m
1 stop
WestJet Logo
10:10 am - 1:50 pm
YWG
-
PDX
5h 40m
1 stop
$239WestJet
Sun, Aug 16 - Mon, Aug 24
WestJet Logo
2:30 pm - 11:40 pm
PDX
-
YWG
7h 10m
1 stop
WestJet Logo
10:10 am - 1:50 pm
YWG
-
PDX
5h 40m
1 stop
$248WestJet
Wed, Aug 12 - Wed, Aug 26
WestJet Logo
2:30 pm - 10:10 pm
PDX
-
YWG
5h 40m
1 stop
WestJet Logo
10:10 am - 1:50 pm
YWG
-
PDX
5h 40m
1 stop
$259WestJet
Sun, Aug 16 - Sun, Aug 23
WestJet Logo
2:30 pm - 11:40 pm
PDX
-
YWG
7h 10m
1 stop
WestJet Logo
10:10 am - 1:50 pm
YWG
-
PDX
5h 40m
1 stop
$263WestJet
Thu, Aug 13 - Tue, Aug 25
WestJet Logo
2:30 pm - 11:40 pm
PDX
-
YWG
7h 10m
1 stop
WestJet Logo
7:00 am - 1:50 pm
YWG
-
PDX
8h 50m
2 stops
$264WestJet
Mon, Aug 17 - Wed, Aug 26
WestJet Logo
2:30 pm - 10:10 pm
PDX
-
YWG
5h 40m
1 stop
WestJet Logo
6:00 am - 1:50 pm
YWG
-
PDX
9h 50m
2 stops
$267WestJet
Sun, Aug 16 - Sun, Aug 23
WestJet Logo
2:30 pm - 10:10 pm
PDX
-
YWG
5h 40m
1 stop
WestJet Logo
6:00 am - 1:50 pm
YWG
-
PDX
9h 50m
2 stops
$268WestJet
Thu, Aug 13 - Mon, Aug 24
WestJet Logo
2:30 pm - 11:40 pm
PDX
-
YWG
7h 10m
1 stop
WestJet Logo
10:10 am - 1:50 pm
YWG
-
PDX
5h 40m
1 stop
$273WestJet
Booking Insights

KAYAK's insights & trends for Portland to Winnipeg flights

Get data-powered insights and trends into flights from Portland to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Portland to Winnipeg?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland to Winnipeg departing in August.

What is the cheapest month to fly from Portland to Winnipeg?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Winnipeg, 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 Portland to Winnipeg is November, where tickets cost $247 (return) on average. On the other hand, the most expensive months are February and April, where the average cost of round-trip tickets is $878 and $638 respectively.

Good to know

Low seasonJanuary
Cheapest flight$106
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 30% lower on average.
Flight from Portland to Winnipeg

When to book flights from Portland to Winnipeg

Are your dates flexible? Find out the best times to travel from Portland to Winnipeg 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 Portland to Winnipeg

  • What is the cheapest flight from Portland to Winnipeg?

    In the last 3 days, the lowest price for a flight from Portland to Winnipeg was $106 for a one-way ticket and $236 for a round-trip.

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

    A passport is required to fly from Portland to Winnipeg.

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

    Portland and Winnipeg are both served by 1 main airport. You will leave Portland from Portland and will be arriving at Winnipeg.

  • Which aircraft models fly most regularly from Portland to Winnipeg?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Portland to Winnipeg?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Portland and Winnipeg, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Portland to Winnipeg, Delta or WestJet?

    The two airlines most popular with KAYAK users for flights from Portland to Winnipeg are Delta and WestJet. With an average price for the route of $431 and an overall rating of 7.9, Delta is the most popular choice. WestJet is also a great choice for the route, with an average price of $403 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Portland to Winnipeg?

    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 Portland to Winnipeg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Winnipeg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Portland 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 Portland to Winnipeg?

    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 Winnipeg with an airline and back to Portland with another airline. Booking your flights between Portland and YWG 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 Portland to Winnipeg?

    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 Winnipeg from Portland 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 serving from Portland to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Portland to Winnipeg. 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 Portland to Winnipeg? 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.
7.9
DeltaOverall score based on 8458 reviews
7.8Entertainment
8.1Boarding
7.9Comfort
7.2Food
8.5Crew
Airline reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

8.0 ExcellentMatthew, May 2026
OKC - ATL
Read more Delta reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Westjet was late and we missed our connecting flight with Cathay. Had to wait 8 hours. Westjet only allows 1 checked in baggage for international flights- it’s always been 2. Canada allows only 1 sandwhich bag size full off small liquids. Everything else will be tossed. Awful trip. Will never fly west jet or go to Toronto to connect flights!

No pre boarding kiosk to check in, baggage claim detected luggage didn’t leave the airport, poorly managed recovery of lost luggage, and blame lost tag from conveyor to TSA/security, very poor from TSA/security check to delivery, crucial if compensation will go thru and will likely wait for months unlike United,

Flight was good, crew was excellent. No complaints at all

Delayed 3 times in a row for 4 hours total. Incrementally pushing back the flight claiming gate delays but they eventually changed the actual plane, due to technical issues. This strategy to avoid compensation to passengers is unprofessional.

The flight was full and good as could be expected. We arrived early which is always a good thing.

Plane seating was uncomfortable, very tight fitting for someone my height, did not recline and overall un enjoyable

Everything was good except for flight delay, but it was because of the snow storm in the arrival airport.

No communication from Kayak or West Jet. Booked extra flights, flights cancelled, no one answers calls. Will be disputing charges.

The trip from LAX to Calgary was aboard a 737-700, which is more than twenty years old. Service was fine, and the food was good, but there was no inflight entertainment, and no WiFi. The flight from Calgary to Vancouver was also delayed more than an hour, due to congestion on the Calgary tarmac. And no food service, but there was in-flight WiFi which made a big difference.

Leg room is a problem the plane was dirty and there were no movies available on the app

I did not like anything because the flight was cancelled yesterday and I did not get to arrive on time in Toronto as I was rebooked with another airline. This caused me to be really stressed out as I am an individual with back injury and to be forced to stay longer in an airport to accommodate a change of airline and the transfers associated with it Due to this I am probably not going to book through your website to eliminate this potentially chaos in the future

shittiest airline in the hemisphere. To improve - start thinking you're flying people, not cattle

Easy boarding, inflight refreshments came on time and comfortable seat

It was good that our flight left early. It was a nice smooth flight and landing.

All good……but luggage didn’t make it on the airplane. Had to wait 3 days. Was a bummer.

Small suitcase used for carryon the last time was refused by boarding crew this time. Appears to be at the discretion and mood of the person on the day. Flight was only half booked, there would have been no problem with space.

It was a problem because there was a delay where we sat before taking off from newark,then when landed in Toronto we sat on tarmac and they wouldn't let us out for a long period of time. When we finally were released to the airport in Toronto the attendant scanned our boarding pass that we were here for our connection to Brazil. We ran all the way to the gate and they said at the gate the door is shut so we can not let you on the plane. We explained that we were checked in by the attendant when we arrived at Toronto airport to go to Brazil and they should not have shut the door. We were ignored at the gate

Flight home was delayed multiple times, did not get home until 2am

the check-in lady at ORD was extremely rude and unprofessional. very disappointed as it was supposed to be a celebration for my wife's birthday and it really put a damper on things. if i wanted to be treated like trash, i would have flown Economy! (as opposed to business class)

My original flight was cancelled and then rebooked four hours later on a recovery flight, but I was checked in as stanby and had no seats so as a family of four we were concerned about not being seated altogether. Our flight then got delayed by another 1.5 hours and when seats were assigned at the gate, three of the four of us were together and we could get my wife closer, they offered no assistance.

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

Information on your arrival and departure airports