PDX - YWG

$360 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 11/10. 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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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, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
1:38 pm - 12:39 amPDX-YWG
9h 01m2 stops
Multiple Airlines Logo
4:55 pm - 9:37 amYWG-PDX
18h 42m1 stop
$360Multiple Airlines
Find Deal
Tue, Mar 10 - Wed, Mar 11
Air Canada Logo
3:15 pm - 1:14 amPDX-YWG
7h 59m1 stop
Air Canada Logo
10:40 am - 2:40 pmYWG-PDX
6h 00m1 stop
$370Air Canada
Find Deal
Wed, Dec 3 - Mon, Dec 8
Delta Logo
12:32 am - 11:45 amPDX-YWG
9h 13m1 stop
Delta Logo
12:35 pm - 5:43 pmYWG-PDX
7h 08m1 stop
$382Delta
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Wed, Dec 3 - Mon, Dec 8
Delta Logo
12:32 am - 11:45 amPDX-YWG
9h 13m1 stop
Delta Logo
12:35 pm - 6:14 pmYWG-PDX
7h 39m2 stops
$392Delta
Find Deal
Tue, Mar 10 - Wed, Mar 11
United Airlines Logo
7:30 pm - 11:39 amPDX-YWG
14h 09m2 stops
United Airlines Logo
2:15 pm - 10:38 pmYWG-PDX
10h 23m2 stops
$399United Airlines
Find Deal
Tue, Mar 10 - Wed, Mar 11
United Airlines Logo
2:00 pm - 11:39 amPDX-YWG
19h 39m2 stops
United Airlines Logo
2:15 pm - 12:34 amYWG-PDX
12h 19m2 stops
$447United Airlines
Find Deal
Tue, Dec 23 - Sun, Dec 28
WestJet Logo
2:11 pm - 11:45 amPDX-YWG
19h 34m1 stop
WestJet Logo
5:45 pm - 8:34 pmYWG-PDX
28h 49m1 stop
$595WestJet
Find Deal
Wed, Dec 3 - Sun, Dec 7
WestJet Logo
12:32 am - 6:06 pmPDX-YWG
15h 34m2 stops
WestJet Logo
10:55 am - 5:43 pmYWG-PDX
32h 48m2 stops
$659WestJet
Find Deal
Fri, Jan 16 - Mon, Jan 19
American Airlines Logo
11:59 pm - 11:35 pmPDX-YWG
45h 36m3 stops
American Airlines Logo
6:00 am - 8:28 pmYWG-PDX
16h 28m2 stops
$668American Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
American Airlines Logo
10:15 pm - 11:35 pmPDX-YWG
23h 20m2 stops
American Airlines Logo
12:10 pm - 10:57 amYWG-PDX
24h 47m3 stops
$676American Airlines
Find Deal

Everything you should know

Top airlines
Air Canada
Cheapest • from $370 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers 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
$360
Overall average: $354
Multiple Airlines
Fri 1/16Mon 1/19
PDX - YWG • 2 stops
Cheapest one-way
$274
Typical prices: $240-$282
Multiple Airlines
Mon 11/10
PDX - YWG • 3 stops
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!
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.

If you are looking for a flight deal from Portland to Winnipeg, look for departures on Fridays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Winnipeg, Thursday is the cheapest day to fly and Saturday is the most expensive.

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 $174 (return) on average. On the other hand, the most expensive months are May and December, where the average cost of round-trip tickets is $470 and $439 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 flight$274
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 $274 for a one-way ticket and $360 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 $476 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 $328 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 8001 reviews
7.3Food
8.5Crew
7.9Comfort
8.2Boarding
7.9Entertainment
Airline reviews

I truly love flying with Delta. They have always treated me with the upmost respect

10.0 ExcellentMAYRA, Nov 2025JFK - MIA
Read more Delta reviews

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

When flying premium on a two our flight a light lunch would have been nice considering the price you pay. A Kit Kat bar and bag of chips is rather cheap service.

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.

Great check in process in LA and good service The check in process as well as at the gate is way better in the US versus canada 🇨🇦

Super experience. Earlier than schedule departure and arrival. Baggage handling was very good

Allow me to book extra bag check in as free though I packed in 1 luggage but that was 7 LBS overweight so make another bag to free check in.

I would like to get my money back. I flight was 4 hours late on the way to detroit, And same on my way back to Brussels they cancelled my flight and give me an other ticket and i had to wait 5 hours.

All attendents were very efficient, pleasant and happy. Everything went smoothly. The seats could have been wider. There could have been more free food instead of just one small bar.

My seat was one of those that couldn't recline, but the problem was that it was abnormally upright, so the headrest actually made the seat concave, which was uncomfortable and hard on my lower back. I had to ball my jacket up and use it as lumbar support. goodness I had it with me.

Boarding was so so after zone 3 was called all other zones went in

I liked a lot , the flight attendant so nice ,the seat very comfortable I enjoyed the flight , I will do it again with Air Canada,

Plane left an hour late, I missed my connection and my bow case was never even loaded on the plane in VA. I deal with this type of nonsense everytime I fly air canada.

For goodness sake, board from the back of the plane to the front and assign overhead space. It would fix everything. Seriously.

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

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