PDX - YWG

$199 Find Cheap Flights from Portland to Winnipeg

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Winnipeg departing on 10/18. 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

Sat, Oct 18 - Fri, Oct 24
Air Canada Logo
3:25 pm - 2:02 amPDX-YWG
8h 37m1 stop
Air Canada Logo
5:05 am - 9:20 amYWG-PDX
6h 15m1 stop
$199Air Canada
Find Deal
Sat, Oct 18 - Fri, Oct 24
Air Canada Logo
7:40 pm - 11:08 amPDX-YWG
13h 28m2 stops
Air Canada Logo
7:10 pm - 11:01 pmYWG-PDX
5h 51m1 stop
$216Air Canada
Find Deal
Sat, Oct 18 - Fri, Oct 24
United Airlines Logo
5:00 am - 10:33 pmPDX-YWG
15h 33m2 stops
United Airlines Logo
7:00 am - 10:45 pmYWG-PDX
17h 45m2 stops
$218United Airlines
Find Deal
Wed, Oct 8 - Sun, Oct 12
Air Canada Logo
3:25 pm - 2:02 amPDX-YWG
8h 37m1 stop
Air Canada Logo
5:05 am - 9:20 amYWG-PDX
6h 15m1 stop
$236Air Canada
Find Deal
Mon, Oct 6 - Mon, Oct 13
Air Canada Logo
7:40 pm - 12:50 pmPDX-YWG
15h 10m1 stop
Air Canada Logo
5:05 am - 9:20 amYWG-PDX
6h 15m1 stop
$259Air Canada
Find Deal
Mon, Oct 6 - Mon, Oct 13
Multiple Airlines Logo
5:15 pm - 1:09 pmPDX-YWG
17h 54m2 stops
Multiple Airlines Logo
5:05 am - 9:20 amYWG-PDX
6h 15m1 stop
$292Multiple Airlines
Find Deal
Fri, Oct 17 - Fri, Oct 24
Delta Logo
12:40 am - 11:30 amPDX-YWG
8h 50m1 stop
Delta Logo
12:20 pm - 8:26 pmYWG-PDX
10h 06m1 stop
$313Delta
Find Deal
Fri, Oct 17 - Fri, Oct 24
Delta Logo
12:40 am - 11:30 amPDX-YWG
8h 50m1 stop
Delta Logo
12:20 pm - 10:40 pmYWG-PDX
12h 20m2 stops
$323Delta
Find Deal
Mon, Nov 3 - Mon, Nov 10
Multiple Airlines Logo
5:41 pm - 12:39 amPDX-YWG
28h 58m2 stops
Multiple Airlines Logo
8:00 am - 9:31 amYWG-PDX
27h 31m1 stop
$349Multiple Airlines
Find Deal
Mon, Nov 3 - Thu, Nov 6
United Airlines Logo
11:59 pm - 11:57 amPDX-YWG
9h 58m1 stop
United Airlines Logo
8:40 am - 10:56 pmYWG-PDX
16h 16m1 stop
$382United Airlines
Find Deal

Everything you should know

Top airlines
Air Canada
Cheapest • from $199 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
5 weeks
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 34% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 47% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$199
Overall average: $338
Air Canada
Sat 10/18Fri 10/24
PDX - YWG • 1 stop
Cheapest one-way
Multiple Airlines
Tue 9/16
PDX - YWG • multi-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!
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 5 weeks before departure, which saves you about 34% 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 flight$199
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly and prices are also 3% 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 $199 for a round-trip ticket.

  • 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?

    Star Alliance, and SkyTeam are the airline alliances operating flights between Portland and Winnipeg, with Star Alliance 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 $484 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 $319 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 7954 reviews
7.9Comfort
7.3Food
8.5Crew
7.9Entertainment
8.2Boarding
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

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

For the price, it was a really good experience. There was no entertainment on board, so I couldn't really rate this, and I didn't order a meal. I appreciated that there was a free glass of wine.

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

My flight from New York to Canada and Canada to Brisbane was canceled, so I had to take united airlines instead flight from New York to Dubai then layover in Dubai 8 hours then from Dubai to Brisbane it was extremely difficult for me , it was a nightmare flying with Canadian airlines unfortunately.

I found the boarding easy and my seat was very comfortable as I had a lot of leg room. I am not too happy that I no longer have lounge access even though I used to get it with my TD credit card.

Flight cancelled. Major disruption to our travel. Do not use Air Canada from KC. To few flights.

Real smooth and easy, Real good leg room in coach!

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

Re luggage I carried a backpack only. I did not check any bags in. However there were other passengers with carry on luggage going in the plane. My question is why are others allowed to have a carry on luggage inside the plane? Shouldn’t they have dropped it off at the gate? I’m asking because I could have brought the same thing instead of a backpack only. Please clarify for future reference. Thank you.

Like the service. Very hard to communicate or contact when have problems

Very bad, flight was cancelled due to strike and staff was unable to rebook us

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

Information on your arrival and departure airports

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