YWG - PDX

C$ 240 Find Cheap Flights from Winnipeg to Portland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Portland departing on 6/6. 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 Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Portland, 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 Winnipeg to Portland, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
C$ 434
Overall average: C$ 589
Delta
Sun 7/6Sat 13/6
YWG - PDX • 1 stop
Cheapest one-way flights
C$ 240
Typical prices: C$ 166-C$ 269
WestJet
Sat 6/6
YWG - PDX • 2 stops
Top airlines
Cheapest • from C$ 434 (round-trip)
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
Not available
There are currently no direct flights between Winnipeg and Portland. You’ll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg C$ 414 (round-trip)
Shortest trip • 6h 03m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 38% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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 Portland!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Winnipeg to Portland (YWG-PDX)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Portland 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 Winnipeg to Portland

Sun, 7 Jun - Sat, 13 Jun
Delta Logo
4:09 p.m. - 11:34 p.m.
YWG
-
PDX
9h 25m
1 stop
Delta Logo
12:40 a.m. - 11:34 a.m.
PDX
-
YWG
8h 54m
1 stop
C$ 434Delta
Sun, 7 Jun - Sat, 13 Jun
Delta Logo
4:09 p.m. - 11:34 p.m.
YWG
-
PDX
9h 25m
1 stop
Delta Logo
12:40 a.m. - 11:34 a.m.
PDX
-
YWG
8h 54m
1 stop
C$ 437Delta
Sun, 7 Jun - Sat, 13 Jun
Delta Logo
4:09 p.m. - 11:34 p.m.
YWG
-
PDX
9h 25m
1 stop
Delta Logo
12:40 a.m. - 11:34 a.m.
PDX
-
YWG
8h 54m
1 stop
C$ 458Delta
Fri, 24 Apr - Fri, 1 May
United Airlines Logo
8:45 a.m. - 10:54 p.m.
YWG
-
PDX
16h 09m
1 stop
United Airlines Logo
3:59 p.m. - 11:52 a.m.
PDX
-
YWG
17h 53m
2 stops
C$ 509United Airlines
Sat, 18 Apr - Mon, 20 Apr
Delta Logo
11:55 a.m. - 8:07 p.m.
YWG
-
PDX
10h 12m
1 stop
Delta Logo
12:30 a.m. - 10:56 a.m.
PDX
-
YWG
8h 26m
1 stop
C$ 511Delta
Sat, 18 Apr - Mon, 20 Apr
Delta Logo
11:55 a.m. - 10:21 p.m.
YWG
-
PDX
12h 26m
2 stops
Delta Logo
12:30 a.m. - 10:56 a.m.
PDX
-
YWG
8h 26m
1 stop
C$ 534Delta
Sat, 18 Apr - Mon, 20 Apr
Delta Logo
11:55 a.m. - 10:21 p.m.
YWG
-
PDX
12h 26m
2 stops
Delta Logo
12:30 a.m. - 10:56 a.m.
PDX
-
YWG
8h 26m
1 stop
C$ 554Delta
Sun, 7 Jun - Sun, 14 Jun
Air Canada Logo
5:45 a.m. - 9:30 a.m.
YWG
-
PDX
5h 45m
1 stop
Air Canada Logo
3:30 p.m. - 12:20 p.m.
PDX
-
YWG
18h 50m
2 stops
C$ 555Air Canada
Sun, 7 Jun - Sun, 14 Jun
Air Canada Logo
5:45 a.m. - 9:30 a.m.
YWG
-
PDX
5h 45m
1 stop
Air Canada Logo
3:30 p.m. - 12:20 p.m.
PDX
-
YWG
18h 50m
2 stops
C$ 557Air Canada
Sun, 7 Jun - Sun, 14 Jun
Air Canada Logo
5:45 a.m. - 9:30 a.m.
YWG
-
PDX
5h 45m
1 stop
Air Canada Logo
3:30 p.m. - 12:20 p.m.
PDX
-
YWG
18h 50m
2 stops
C$ 558Air Canada
Booking Insights

KAYAK's insights & trends for Winnipeg to Portland flights

Get data-powered insights and trends into flights from Winnipeg to Portland to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Winnipeg to Portland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Portland, 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 Winnipeg to Portland is August, where tickets cost C$ 304 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is C$ 683 and C$ 625 respectively.

Good to know

Low seasonJanuary
Cheapest flightC$ 240
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 27% lower on average.
Flight from Winnipeg to Portland

When to book flights from Winnipeg to Portland

Are your dates flexible? Find out the best times to travel from Winnipeg to Portland 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 Winnipeg to Portland

  • What is the cheapest flight from Winnipeg to Portland?

    In the last 3 days, the lowest price for a flight from Winnipeg to Portland was C$ 240 for a one-way ticket and C$ 434 for a round-trip.

  • Which aircraft models fly most regularly from Winnipeg to Portland?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Winnipeg to Portland?

    Star Alliance is the only airline alliance operating flights between Winnipeg and Portland.

  • Which is the best airline for flights from Winnipeg to Portland, WestJet or Air Canada?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Portland are WestJet and Air Canada. With an average price for the route of C$ 365 and an overall rating of 7.2, WestJet is the most popular choice. Air Canada is also a great choice for the route, with an average price of C$ 459 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Winnipeg to Portland?

    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 Winnipeg to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Winnipeg 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 Winnipeg to Portland?

    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 Portland with an airline and back to Winnipeg with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Portland?

    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 Portland from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Winnipeg to Portland

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to Portland. 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 Winnipeg to Portland? 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 3288 reviews
7.9Crew
6.1Entertainment
6.2Food
7.4Boarding
7.0Comfort
Airline reviews

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

10.0 ExcellentAnonymous, Mar 2026
YLW - SEA
Read more WestJet reviews

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

The window seat on the emergency row was too small. I had a different seat booked and they moved me. My seat remained open. It was very uncomfortable.

Experience was good, the wifi hook up is somewhat tough

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

Overall good experience. The wait for baggage at our destination was quite long, but other than that everything was good as expected

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

My ticket did not exist when I got to the airport. I had to book another flight and was still charged by Kayak

Got denied my flight was told on Google that Air Canada was supposed to book me a flight back home because I never was able to go to my destination. They did not help me whatsoever. I had to book a whole new flight for that reason I would write this is zero

The plane was delayed an hour. Heard from other passengers that the Vancouver connection to SFO was never on-time.

My experience was good with United too But only not so good thing was that at Calgary airport I was not given lounge access despite of flying business. Aspire lounge denied it to me, which was unfair I feel

We left over 2 hours late and they didn't even give us a complimentary snack, when getting to the desk I asked if I could be put in a row with only 1 other person or an empt y one I was told the flight was full when the last two rows were empty. All around over it

they were super helpful. Agents at the desk got me on an earlier flight and I was able to get home several hours earlier.

This is a great non-stop YVR-MIA. Very comfortable plane, and no transfer through a city that gets major winter weather!

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

Air Canada’s problems are not staff related by and large, no. The problem is tiny jets between the U.S. and Canada - yes, believe it or not they are still “international” (just ask our own Mango Maniac in power in the U.S.). The little aisle is compounded by a design flaw of a “dog leg” starting at seat 12. Woe be unto you if you sit here as passengers and attendants do not have sufficient room to not hit you in the face with backpacks. One thing I will say very positively about Air Canada is you still provide pillows and blankets on transcontinental flights to all, not just the elites. Your tiny improperly designed jets are also a problem flying city to city within Canada also. One can only say you remind us of a “Jet Blue” or “Spirit” experience. Also your luggage space is downright Byzantine! We will endeavor to avoid you and use other U.S. carriers, albeit charging more.

Terrible canceled flight and lost my luggage. Flew me to Halifax. Tgat flight was delayed, had to spend night in airport chair.

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

Information on your arrival and departure airports