PDX - YWG

C$ 266 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 19/5. 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
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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
C$ 462
WestJet
Mon 15/6Tue 16/6
PDX - YWG • 1 stop
Cheapest one-way flights
C$ 266
Typical prices: C$ 100-C$ 255
Air Canada
Tue 19/5
PDX - YWG • 1 stop
Top airlines
WestJet
Cheapest • from C$ 462 (round-trip)
WestJet
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct 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
Calgary (YYC)
Cheapest • Avg C$ 322 (round-trip)
Calgary (YYC)
Shortest trip • 5h 57m (one-way)
Insights
Insights
Insights
Insights
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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 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

Mon, 15 Jun - Tue, 16 Jun
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
C$ 462WestJet
Wed, 29 Apr - Wed, 6 May
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
WestJet Logo
7:00 a.m. - 1:50 p.m.
YWG
-
PDX
8h 50m
2 stops
C$ 465WestJet
Wed, 29 Apr - Wed, 6 May
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
C$ 469WestJet
Thu, 11 Jun - Tue, 16 Jun
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
C$ 484WestJet
Wed, 13 May - Sun, 17 May
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
C$ 490WestJet
Thu, 11 Jun - Mon, 15 Jun
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
C$ 495WestJet
Thu, 11 Jun - Tue, 16 Jun
WestJet Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
WestJet Logo
7:00 a.m. - 1:50 p.m.
YWG
-
PDX
8h 50m
2 stops
C$ 502WestJet
Fri, 15 May - Sun, 17 May
WestJet Logo
2:30 p.m. - 9:20 a.m.
PDX
-
YWG
16h 50m
2 stops
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
C$ 506WestJet
Wed, 13 May - Mon, 18 May
Multiple Airlines Logo
2:30 p.m. - 10:10 p.m.
PDX
-
YWG
5h 40m
1 stop
Multiple Airlines Logo
4:55 p.m. - 9:29 a.m.
YWG
-
PDX
18h 34m
2 stops
C$ 510Multiple Airlines
Wed, 13 May - Sun, 17 May
WestJet Logo
2:30 p.m. - 12:55 a.m.
PDX
-
YWG
8h 25m
1 stop
WestJet Logo
10:10 a.m. - 1:50 p.m.
YWG
-
PDX
5h 40m
1 stop
C$ 516WestJet
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.

Which airlines provide the cheapest flights from Portland to Winnipeg?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Portland to Winnipeg were found on WestJet (C$ 462) and Air Canada (C$ 519).

Find deals

Good to know

Low seasonNovember
Cheapest flightC$ 266
Best time to beat the crowds (43% less expensive on average)
Most popular time to fly and prices are also 25% 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 C$ 266 for a one-way ticket and C$ 462 for a round-trip.

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

    When flying out of Portland you will be using Portland. You will be landing at Winnipeg, also known as Winnipeg.

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

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

  • 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.

  • 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 airline flying 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.
7.2
WestJetOverall score based on 3295 reviews
7.9Crew
7.4Boarding
6.2Food
7.0Comfort
6.1Entertainment
Airline reviews

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,

2.0 MediocreMaria, Feb 2026
IAH - YYC
Read more WestJet reviews

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

The personal item sizer cannot take a standard backpack, and the cabin luggage sizer cannot take a standard carry-on. Designed for people from the island of Lilliput!!. and also compels people to pay additional fees to check their bags. Making money by ticking off the passengers is a very short-sighted business strategy, especially since they have a choice of carriers

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

Information on your arrival and departure airports

Portland (PDX)
Winnipeg (YWG)