PDX - YWG

$156 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 4/14. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$351
Air Canada
Fri 6/12Sun 6/21
PDX - YWG • 1 stop
Cheapest one-way
$156
Typical prices: $174-$216
Delta
Tue 4/14
PDX - YWG • 1 stop
Top airlines
Cheapest • from $351 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Portland and Winnipeg. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $323 (round-trip)
Shortest trip • 6h 01m (one-way)
Insights
Insights
Insights
Insights
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, Jun 12 - Sun, Jun 21
Air Canada Logo
7:45 pm - 1:04 pm
PDX
-
YWG
15h 19m
1 stop
Air Canada Logo
5:40 am - 9:31 am
YWG
-
PDX
5h 51m
1 stop
$351Air Canada
Fri, Jun 12 - Sun, Jun 21
Air Canada Logo
7:45 pm - 12:20 pm
PDX
-
YWG
14h 35m
2 stops
Air Canada Logo
5:40 am - 9:31 am
YWG
-
PDX
5h 51m
1 stop
$368Air Canada
Fri, May 8 - Wed, May 13
WestJet Logo
2:30 pm - 9:20 am
PDX
-
YWG
16h 50m
2 stops
WestJet Logo
7:00 am - 1:50 pm
YWG
-
PDX
8h 50m
2 stops
$397WestJet
Wed, Apr 29 - Sat, May 2
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m
1 stop
Air Canada Logo
5:40 am - 9:30 am
YWG
-
PDX
5h 50m
1 stop
$399Air Canada
Wed, Apr 29 - Sat, May 2
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m
1 stop
Air Canada Logo
7:20 am - 2:45 pm
YWG
-
PDX
9h 25m
2 stops
$404Air Canada
Fri, May 8 - Wed, May 13
WestJet Logo
2:30 pm - 12:55 am
PDX
-
YWG
8h 25m
1 stop
WestJet Logo
7:00 am - 1:50 pm
YWG
-
PDX
8h 50m
2 stops
$405WestJet
Wed, May 6 - Mon, May 11
United Airlines Logo
11:55 pm - 11:52 am
PDX
-
YWG
9h 57m
1 stop
United Airlines Logo
2:00 pm - 10:35 pm
YWG
-
PDX
10h 35m
1 stop
$413United Airlines
Sun, May 3 - Sun, May 10
United Airlines Logo
10:55 pm - 11:52 am
PDX
-
YWG
10h 57m
1 stop
United Airlines Logo
2:00 pm - 11:55 pm
YWG
-
PDX
11h 55m
1 stop
$414United Airlines
Thu, May 14 - Sun, May 17
Air Canada Logo
3:30 pm - 2:04 am
PDX
-
YWG
8h 34m
1 stop
Air Canada Logo
5:40 am - 9:30 am
YWG
-
PDX
5h 50m
1 stop
$418Air Canada
Wed, May 6 - Mon, May 11
United Airlines Logo
7:45 pm - 11:52 am
PDX
-
YWG
14h 07m
2 stops
United Airlines Logo
2:00 pm - 10:35 pm
YWG
-
PDX
10h 35m
1 stop
$423United 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.

Which airlines provide the cheapest flights from Portland to Winnipeg?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Portland to Winnipeg were found on Air Canada ($351) and WestJet ($397).

Good to know

Low seasonNovember
Cheapest flight$156
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly and prices are also 25% 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 $156 for a one-way ticket and $351 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 $424 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 $266 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 8318 reviews
7.8Entertainment
7.9Comfort
8.1Boarding
7.2Food
8.5Crew
Airline reviews

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

2.0 MediocreSreekumar, Mar 2026
FLL - DTW
Read more Delta reviews

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

No pre boarding kiosk to check in, baggage claim detected luggage didn’t leave the airport, poorly managed recovery of lost luggage, and blame lost tag from conveyor to TSA/security, very poor from TSA/security check to delivery, crucial if compensation will go thru and will likely wait for months unlike United,

Flight was good, crew was excellent. No complaints at all

Delayed 3 times in a row for 4 hours total. Incrementally pushing back the flight claiming gate delays but they eventually changed the actual plane, due to technical issues. This strategy to avoid compensation to passengers is unprofessional.

The flight was full and good as could be expected. We arrived early which is always a good thing.

Plane seating was uncomfortable, very tight fitting for someone my height, did not recline and overall un enjoyable

Everything was good except for flight delay, but it was because of the snow storm in the arrival airport.

No communication from Kayak or West Jet. Booked extra flights, flights cancelled, no one answers calls. Will be disputing charges.

The trip from LAX to Calgary was aboard a 737-700, which is more than twenty years old. Service was fine, and the food was good, but there was no inflight entertainment, and no WiFi. The flight from Calgary to Vancouver was also delayed more than an hour, due to congestion on the Calgary tarmac. And no food service, but there was in-flight WiFi which made a big difference.

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

The most uncomfortable flight I’ve ever been on. I’m only 5,4” and barely had enough room to exist, couldn’t even fully relax my shoulders. Not sure why they bother with snacks. Half a coke and a single cookie?? Wow. Purchasable food looked gross too. Remember when airlines used to treat you like a human being?

Departed Palm Springs over an hour late because there’s only one gate, and it has always delayed by the arriving and departing flight to Toronto and the arriving flight from Vancouver.

I checked a bag and there was only one agent to assist all customers with any issues.

I want to thank Carlos at the Miami AC desk - he was amazing and went over and above to help us out. Thank you Carlos and all the best to you!!! You made our faith in AC feel great! Sincerely, David Cubitt

Flight was canceled due to mechanical issues. After a considerable wait in the queue, Air Canada customer service was very helpful to get us on another flight. I am disappointed to report our rescheduled flight is for three days from now. Three days of extra expenses and inconvenience is unacceptable.

Extremely disappointing. My original Denver–Vancouver–Bangkok itinerary was cancelled due to a crewing issue. I was not proactively supported and had to drive back home after already reaching the airport. Communication was poor throughout, and attempts to contact customer service resulted in being on hold for nearly three hours without reaching anyone. Instead of being rebooked on the same direct routing the following day, I was rerouted onto a much longer itinerary via multiple cities and airlines, which resulted in arriving approximately 30 hours later than scheduled. At Denver airport, there was no visible Air Canada representative available to properly assist. Ground staff offered no real support beyond directing passengers to a phone number. There was no clear communication, no ownership, and no meaningful customer care during a major disruption. The final journey involved three flights instead of the original two, significantly increasing travel time and stress. Overall, the handling of the cancellation and lack of customer support was unacceptable. What could have been better? Clear communication during the cancellation Accessible customer service (phone support that actually answers) Proper in-person assistance at the airport Rebooking onto a comparable routing rather than a significantly longer one

Great setup on both flights except the last flight we got condensed dripping all over me in the last 20 mins of the flight

The last 3 hours it was freezing cold in row 56. Multiple people had their winter coats on and were utilizing the blankets provided by the airline. I also did not have easy access to figure out how to book my food allergy and advance for my meals. Most of everything I received was something I couldn't eat. This needs to be made more accessible. Also, I'm 5'10 which is the average height of the American male. I flew from Philadelphia to Toronto and then to Tokyo and the seats were absolutely unbearable. For that long of a flight it is impossible to get comfortable when doing anything. Flights need to have more space and stop prioritizing costs over people.

Was delayed at every point/ connection. Luggages missing for 5days. Had no medications for diabetes and high B/p. when bags where finally delivered on the 30th, the insulin and ozempic were no longer patent, as the ice pack had since dissolved and the authenticity of the med is now questionable, since they must be refrigerated. Please have them refund my bag fees. I should sue them for all the inconveniences caused to me.

The plane was delayed substantially due to a mechanical problem, that being said, the airline was very fair with providing a meal coupon for us. I would rather arrive late on a mechanically sound plane than the alternative. The food served in the plane was just awful, however and I recommend a new catering company.

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

Information on your arrival and departure airports