PDX - YWG

C$ 130 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 27/9. 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 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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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

Wed, 8 Oct - Sun, 12 Oct
Air Canada Logo
3:25 p.m. - 11:35 p.m.PDX-YWG
6h 10m1 stop
Air Canada Logo
6:25 p.m. - 11:01 p.m.YWG-PDX
6h 36m1 stop
C$ 328Air Canada
Find Deal
Mon, 6 Oct - Mon, 13 Oct
Air Canada Logo
7:40 p.m. - 12:50 p.m.PDX-YWG
15h 10m1 stop
Air Canada Logo
5:05 a.m. - 9:20 a.m.YWG-PDX
6h 15m1 stop
C$ 355Air Canada
Find Deal
Wed, 8 Oct - Sun, 12 Oct
 Logo
3:50 p.m. - 1:09 p.m.PDX-YWG
19h 19m2 stops
 Logo
5:05 a.m. - 9:20 a.m.YWG-PDX
6h 15m1 stop
C$ 366
Find Deal
Mon, 10 Nov - Tue, 18 Nov
Air Canada Logo
3:15 p.m. - 1:09 a.m.PDX-YWG
7h 54m1 stop
Air Canada Logo
10:45 a.m. - 2:45 p.m.YWG-PDX
6h 00m1 stop
C$ 367Air Canada
Find Deal
Tue, 11 Nov - Tue, 18 Nov
Delta Logo
7:59 p.m. - 11:48 a.m.PDX-YWG
13h 49m2 stops
Delta Logo
5:50 p.m. - 10:55 a.m.YWG-PDX
19h 05m2 stops
C$ 464Delta
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Tue, 11 Nov - Mon, 17 Nov
Delta Logo
12:35 a.m. - 11:48 a.m.PDX-YWG
9h 13m1 stop
Delta Logo
5:50 p.m. - 8:35 a.m.YWG-PDX
16h 45m2 stops
C$ 540Delta
Find Deal
Mon, 6 Oct - Mon, 13 Oct
WestJet Logo
1:45 p.m. - 11:26 a.m.PDX-YWG
19h 41m2 stops
WestJet Logo
6:30 a.m. - 1:05 p.m.YWG-PDX
8h 35m2 stops
C$ 572WestJet
Find Deal
Wed, 8 Oct - Sun, 12 Oct
 Logo
5:15 p.m. - 1:09 p.m.PDX-YWG
17h 54m2 stops
 Logo
6:15 a.m. - 2:46 p.m.YWG-PDX
10h 31m2 stops
C$ 615
Find Deal
Fri, 16 Jan - Mon, 19 Jan
United Airlines Logo
3:45 p.m. - 11:57 a.m.PDX-YWG
18h 12m2 stops
United Airlines Logo
2:20 p.m. - 10:32 p.m.YWG-PDX
10h 12m1 stop
C$ 693United Airlines
Find Deal
Mon, 10 Nov - Wed, 19 Nov
United Airlines Logo
7:38 p.m. - 11:57 a.m.PDX-YWG
14h 19m2 stops
United Airlines Logo
8:40 a.m. - 6:36 p.m.YWG-PDX
11h 56m2 stops
C$ 700United Airlines
Find Deal

Everything you should know

Top airlines
Air Canada
Cheapest • from C$ 328 (round-trip)
WestJet
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
5 weeks
in advance
Our data shows that travellers who book at least 5 weeks in advance save around 21% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 48% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 328
Overall average: C$ 533
Air Canada
Wed 8/10Sun 12/10
PDX - YWG • 1 stop
Cheapest one-way flights
C$ 130
Typical prices: C$ 447-497
WestJet
Sat 27/9
PDX - YWG • 2 stops
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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!
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.

What’s the cheapest day of the week to fly from Portland to Winnipeg?

The average price of all round-trip flights from Portland to Winnipeg clicked on KAYAK for each day over the last 12 months.

When flying from Portland to Winnipeg, you should consider leaving on a Thursday and avoid Fridays if you are looking for the best rates. For your return to Portland, you’ll find the best rates on Sundays and the most expensive ones on Mondays.

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 February, where tickets cost C$ 241 (return) on average. On the other hand, the most expensive months are May and December, where the average cost of round-trip tickets is C$ 651 and C$ 608 respectively.

How far in advance should I book a flight from Portland to Winnipeg?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Portland to Winnipeg, you should book around 5 weeks before departure, which saves you about 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flightC$ 130
Best time to beat the crowds (49% less expensive on average)
Most popular time to fly and prices are also 6% 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$ 94 for a one-way ticket and C$ 237 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.

  • Which airline alliances offer flights from Portland to Winnipeg?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Portland and Winnipeg, with Star Alliance being the most commonly used for this 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 3091 reviews
7.4Boarding
6.1Entertainment
7.1Comfort
6.2Food
7.9Crew
Airline reviews

I like the web site, prompt notifications, website checks in process, and airport check in. The flight attendants are attentive and polite. The return flight was 2 hours late and reason vine doesn't sound like an unplanned and unexpected issue (scheduled plane maintenance).

8.0 ExcellentAnonymous, Aug 2025LAS - YVR
Read more WestJet reviews

I like the web site, prompt notifications, website checks in process, and airport check in. The flight attendants are attentive and polite. The return flight was 2 hours late and reason vine doesn't sound like an unplanned and unexpected issue (scheduled plane maintenance).

Our flight was delayed almost 3.5 hours (some of the issue seemed to be weather-related, yes) but NOTHING was offered as an conciliatory gesture for this delay. No food offering or any additional drink offering. There is no entertainment is available on any screen behind the seats. The airlines are so quick to penalize customers for slightest requests for comfort- seat changes, complicated baggage allowances, seating zones which are utterly dehumanizing (ZONE 9? after Zone 4- why? This is so clearly meant to be a message to those that do not have 'loyalty' to this airline to make a distinguishing line in the sand. There is such a lack of humanity in the way people are corralled in and spoken to. So, I don't think airlines should be all that surprised when those some dehumanizing corporate treatment is returned to them when asked. The flight on the way into Calgary was scheduled to arrived at 9:25 and we arrived at 12:45 AM. It is not okay. I would think TWICE and possibly once more before booking with them again. Their overhead bins are small and limited so they bully you into either paying for a $90 checked bag or gate check a lot of people's bags. Often on their website there is no carry-on bag allowance. Beware!

everything was fine expect massive delays - not the airline’s fault

The checked luggage still hasn't arrived yet. 42 h later. We saw it being unloaded in the stopover location. It was. 5 hour layover so it wasn't a rushed transfer. One positive aspect, it was close to being on time and the crew that came on the clean the plane was very efficient.

They cancelled and moved my flight with no email or text or any other notice. I discovered this only when I attempted to check in for my flight. Actual flying experience was above average.

They were on time and everything went as expected. The only thing that could be better was they didn't wait for us to get through customs to pick up our luggage off the carousel. An employee picked it up and was shoving it together with others onto a cart. Later we found one of our luggage was slightly bent.

Delayed boarding. Delayed taking off. Delayed landing. Missed our connecting flight. Our seats on this plane were not assigned until last minute, splitting up our family with kids. I sat in the last row next to the bathroom with so many people rubbing up against me to get to the bathroom the entire flight.

Another delayed flight. Then got bumped to a later connecting flight, over two hours later! Plane was hot and uncomfortable.

Asked to cancel flight 6 days in advance of flight back to St. Louis, MO. Would not allow. No credit either.

Crew was nice especially by North American standards. Bad good. No entertainment screens. Terrible WiFi

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

Information on your arrival and departure airports

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