PDX - YWG

$293 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 1/4. 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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Everything you should know

Cheapest round-trip
$391
Multiple Airlines
Fri 1/16Sun 1/18
PDX - YWG • 2 stops
Cheapest one-way
$293
Overall average: $279
WestJet
Sun 1/4
PDX - YWG • 1 stop
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, Jan 16 - Sun, Jan 18
Multiple Airlines Logo
7:20 am - 10:41 pm
PDX
-
YWG
13h 21m2 stops
Multiple Airlines Logo
4:55 pm - 11:52 pm
YWG
-
PDX
8h 57m1 stop
$391Multiple Airlines
Mon, Jan 12 - Thu, Jan 15
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m1 stop
Air Canada Logo
10:45 am - 2:40 pm
YWG
-
PDX
5h 55m1 stop
$418Air Canada
Mon, Jan 12 - Thu, Jan 15
Air Canada Logo
9:50 am - 6:09 pm
PDX
-
YWG
6h 19m1 stop
Air Canada Logo
10:45 am - 2:40 pm
YWG
-
PDX
5h 55m1 stop
$428Air Canada
Tue, Jan 6 - Sat, Jan 10
Air Canada Logo
9:50 am - 6:09 pm
PDX
-
YWG
6h 19m1 stop
Air Canada Logo
9:50 pm - 9:15 am
YWG
-
PDX
13h 25m1 stop
$437Air Canada
Mon, Jan 12 - Thu, Jan 15
Air Canada Logo
7:00 pm - 3:43 pm
PDX
-
YWG
18h 43m2 stops
Air Canada Logo
10:45 am - 2:40 pm
YWG
-
PDX
5h 55m1 stop
$449Air Canada
Wed, Dec 31 - Mon, Jan 5
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m1 stop
Air Canada Logo
9:50 pm - 9:15 am
YWG
-
PDX
13h 25m1 stop
$450Air Canada
Tue, Jan 6 - Sat, Jan 10
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m1 stop
Air Canada Logo
9:50 pm - 9:15 am
YWG
-
PDX
13h 25m1 stop
$454Air Canada
Mon, Jan 12 - Thu, Jan 15
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m1 stop
Air Canada Logo
8:00 am - 6:30 pm
YWG
-
PDX
12h 30m2 stops
$460Air Canada
Tue, Jan 6 - Sat, Jan 10
Air Canada Logo
9:50 am - 6:09 pm
PDX
-
YWG
6h 19m1 stop
Air Canada Logo
8:00 am - 9:15 am
YWG
-
PDX
27h 15m2 stops
$486Air Canada
Tue, Jan 6 - Sat, Jan 10
Multiple Airlines Logo
7:00 am - 12:34 am
PDX
-
YWG
15h 34m1 stop
Multiple Airlines Logo
9:00 pm - 9:34 am
YWG
-
PDX
38h 34m2 stops
$516Multiple Airlines
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.

Good to know

Low seasonFebruary
Cheapest flight$293
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly and prices are also 5% 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 $293 for a one-way ticket and $391 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 $472 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 8009 reviews
7.3Food
7.9Comfort
8.1Boarding
7.9Entertainment
8.5Crew
Airline reviews

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

2.0 MediocreWilliam, Dec 2025
DAL - ATL
Read more Delta reviews

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

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

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!

Nothing specific. Cabin temperature was too high for some reason.

It was just fine. I managed to make all my connection too sbut had trouble in Munich with no wheel chair and trouble trying to get help from the airport people to get to the other terminal for my flight. Finally a wonderful lady Amelia, helped me to make my flight connection Timon with zero time to spare.

Over 40 years ago my AC return flight was canceled, during this last summer the same thing happened. AC denied everything Canadian like paying for accommodations and basic necessities. So why would I ever want to fly AC again? This last flight my wife took the return flight had problems and left late, so I guess they are getting better. However I have no faith in this airline so I drove to this last destination! I'll never fly AC again!!!

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

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

Information on your arrival and departure airports