PDX - YWG

C$ 306 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 5/12. 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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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, 12 Jan - Thu, 15 Jan
Multiple Airlines Logo
2:53 p.m. - 12:43 a.m.PDX-YWG
7h 50m1 stop
Multiple Airlines Logo
12:40 p.m. - 11:52 p.m.YWG-PDX
13h 12m2 stops
C$ 422Multiple Airlines
Find Deal
Mon, 12 Jan - Thu, 15 Jan
Multiple Airlines Logo
7:14 a.m. - 12:43 a.m.PDX-YWG
15h 29m1 stop
Multiple Airlines Logo
7:30 a.m. - 10:33 a.m.YWG-PDX
29h 03m1 stop
C$ 442Multiple Airlines
Find Deal
Thu, 4 Dec - Sat, 6 Dec
Delta Logo
5:30 a.m. - 4:55 p.m.PDX-YWG
9h 25m2 stops
Delta Logo
6:40 a.m. - 1:14 p.m.YWG-PDX
8h 34m2 stops
C$ 578Delta
Find Deal
Thu, 4 Dec - Sat, 6 Dec
Air Canada Logo
3:15 p.m. - 1:14 a.m.PDX-YWG
7h 59m1 stop
Air Canada Logo
10:45 a.m. - 2:40 p.m.YWG-PDX
5h 55m1 stop
C$ 581Air Canada
Find Deal
Tue, 10 Mar - Wed, 11 Mar
Air Canada Logo
9:50 a.m. - 6:09 p.m.PDX-YWG
6h 19m1 stop
Air Canada Logo
8:00 a.m. - 2:40 p.m.YWG-PDX
8h 40m2 stops
C$ 588Air Canada
Find Deal
Wed, 3 Dec - Sun, 7 Dec
Delta Logo
12:32 a.m. - 11:45 a.m.PDX-YWG
9h 13m1 stop
Delta Logo
12:35 p.m. - 10:40 p.m.YWG-PDX
12h 05m2 stops
C$ 593Delta
Find Deal
Tue, 10 Mar - Wed, 11 Mar
United Airlines Logo
7:30 p.m. - 11:39 a.m.PDX-YWG
14h 09m2 stops
United Airlines Logo
2:15 p.m. - 10:38 p.m.YWG-PDX
10h 23m2 stops
C$ 623United Airlines
Find Deal
Tue, 23 Dec - Sun, 28 Dec
WestJet Logo
12:29 p.m. - 10:41 p.m.PDX-YWG
8h 12m2 stops
WestJet Logo
5:45 p.m. - 8:34 p.m.YWG-PDX
28h 49m1 stop
C$ 823WestJet
Find Deal
Fri, 5 Dec - Sat, 6 Dec
United Airlines Logo
6:00 a.m. - 8:55 p.m.PDX-YWG
12h 55m3 stops
United Airlines Logo
2:20 p.m. - 10:15 p.m.YWG-PDX
9h 55m1 stop
C$ 858United Airlines
Find Deal
Fri, 26 Dec - Fri, 2 Jan
WestJet Logo
12:16 p.m. - 11:45 a.m.PDX-YWG
21h 29m1 stop
WestJet Logo
2:40 p.m. - 4:40 p.m.YWG-PDX
28h 00m2 stops
C$ 904WestJet
Find Deal

Everything you should know

Top airlines
Delta
Cheapest • from C$ 578 (round-trip)
WestJet
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travellers who book at least 4 weeks in advance save around 50% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 46% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 422
Overall average: C$ 493
Multiple Airlines
Mon 12/1Thu 15/1
PDX - YWG • 1 stop
Cheapest one-way flights
C$ 184
Typical prices: C$ 252-C$ 362
Multiple Airlines
Fri 5/12
PDX - YWG • 3 stops
Start a new search
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$ 242 (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$ 655 and C$ 612 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 4 weeks before departure, which saves you about 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flightC$ 184
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 1% 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$ 184 for a one-way ticket and C$ 422 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 3148 reviews
6.1Entertainment
7.1Comfort
7.9Crew
6.2Food
7.4Boarding
Airline reviews

What do you expect from a Dash 8 plane? No seats really comfortable.

8.0 ExcellentGordon, Sep 2025YXE - YWG
Read more WestJet reviews

What do you expect from a Dash 8 plane? No seats really comfortable.

my wife got very sick and we did not travel . we booked and bought the travel insurance and dot nothing but hassle and a triangle of stress in trying to make the insurance claim I called in and was told they would not give me anything in writing to say they would not refund my money back this make it impossible to file the claim I will never book with Kayak again.

We got delayed to the point of having a 20 hour layover. That is absurd. I couldn’t believe it. I’m furious.

Kayak was the problem! The tickets we bought did not allow for carry on or checked luggage and we ended up paying more for those services than the tickets! The paperwork Kayak provided for the receipt left the luggage policy for Westair intentionally blank. This was intentionally decietful on Kayak's part. Our additional cost was over $400.00! I will be calling customer service today asking for refunds and I will keep you informed on any review sites as I can. Keith

Leaving the same day as planned would've been better

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.

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

Information on your arrival and departure airports

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