YWG - PDX

C$ 192 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 1/9. 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 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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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

Thu, 11 Sep - Sat, 13 Sep
 Logo
8:30 a.m. - 8:25 p.m.YWG-PDX
13h 55m2 stops
 Logo
1:45 p.m. - 12:30 a.m.PDX-YWG
8h 45m1 stop
C$ 400
Find Deal
Thu, 11 Sep - Sat, 13 Sep
WestJet Logo
8:30 a.m. - 1:04 p.m.YWG-PDX
6h 34m1 stop
WestJet Logo
1:45 p.m. - 11:10 p.m.PDX-YWG
7h 25m1 stop
C$ 427WestJet
Find Deal
Thu, 11 Sep - Sat, 13 Sep
United Airlines Logo
4:25 p.m. - 8:51 a.m.YWG-PDX
18h 26m2 stops
United Airlines Logo
5:00 a.m. - 10:33 p.m.PDX-YWG
15h 33m2 stops
C$ 436United Airlines
Find Deal
Thu, 18 Dec - Thu, 1 Jan
Air Canada Logo
10:45 a.m. - 2:45 p.m.YWG-PDX
6h 00m1 stop
Air Canada Logo
9:50 a.m. - 6:09 p.m.PDX-YWG
6h 19m1 stop
C$ 454Air Canada
Find Deal
Thu, 18 Dec - Thu, 1 Jan
Air Canada Logo
10:45 a.m. - 2:45 p.m.YWG-PDX
6h 00m1 stop
Air Canada Logo
3:15 p.m. - 1:09 a.m.PDX-YWG
7h 54m1 stop
C$ 455Air Canada
Find Deal
Thu, 18 Dec - Thu, 1 Jan
Air Canada Logo
8:00 a.m. - 6:30 p.m.YWG-PDX
12h 30m2 stops
Air Canada Logo
3:15 p.m. - 1:09 a.m.PDX-YWG
7h 54m1 stop
C$ 507Air Canada
Find Deal
Thu, 18 Dec - Thu, 1 Jan
Air Canada Logo
8:00 a.m. - 6:30 p.m.YWG-PDX
12h 30m2 stops
Air Canada Logo
9:50 a.m. - 6:09 p.m.PDX-YWG
6h 19m1 stop
C$ 509Air Canada
Find Deal
Thu, 11 Sep - Sat, 13 Sep
 Logo
3:15 p.m. - 11:11 a.m.YWG-PDX
21h 56m3 stops
 Logo
1:45 p.m. - 2:13 p.m.PDX-YWG
22h 28m2 stops
C$ 572
Find Deal
Thu, 18 Dec - Thu, 1 Jan
Air Canada Logo
8:00 a.m. - 6:30 p.m.YWG-PDX
12h 30m2 stops
Air Canada Logo
3:54 p.m. - 12:59 p.m.PDX-YWG
19h 05m2 stops
C$ 634Air Canada
Find Deal
Thu, 11 Sep - Fri, 12 Sep
WestJet Logo
8:30 a.m. - 1:04 p.m.YWG-PDX
6h 34m1 stop
WestJet Logo
12:45 a.m. - 4:50 p.m.PDX-YWG
14h 05m1 stop
C$ 662WestJet
Find Deal
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’s the cheapest day of the week to fly from Winnipeg to Portland?

The average price of all round-trip flights from Winnipeg to Portland clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Portland on a Sunday and more expensive on a Monday. On your return trip to Winnipeg, you should consider flying back on a Thursday, and avoid Fridays for better deals.

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$ 312 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is C$ 591 and C$ 557 respectively.

How far in advance should I book a flight from Winnipeg to Portland?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Winnipeg to Portland, you should book around 3 weeks before departure, which saves you about 59% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flightC$ 192
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 9% 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$ 139 for a one-way ticket and C$ 290 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, United Airlines or WestJet?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Portland are United Airlines and WestJet. With an average price for the route of C$ 408 and an overall rating of 7.4, United Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of C$ 379 and an overall rating of 7.2.

  • 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 4 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.
8.0
DeltaOverall score based on 7982 reviews
8.2Boarding
7.9Entertainment
7.9Comfort
8.5Crew
7.3Food
Airline reviews

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

2.0 MediocreMichael, Aug 2025SLC - CDC
Read more Delta reviews

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

Our seats were comfortable with adequate room to stretch out and recline. The food was tasty and served it just the right intervals. Our flight attendant was extra attentive and friendly. Flight arrived early. And the most turbulence. Overall that’s good and experience for an 11 hour flight as can be hoped for

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

They made us board and then deboard due to mechanical issue which delayed the departure by almost 2 hours and we barely made our connecting flight. These quality checks should've been done before boarding not after.

Having to up charge for a seat assignment is not good. Delta can do better

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

Michael, our FA was very attentive, even finding me a chocolate brownie from economy class when the dessert selections were all dairy based. ( intolerant, not allergic so don’t usually need to order dairy free)

We tried to upgrade to economy premium but were told this was not possible as we had booked through United Airlines (and Air Canada was operating the flight). This seemed silly given there was ample space in economy premium. Additionally, we had to wait almost 1.5 hours upon arrival to taxi to the gate. Otherwise, the crew were very pleasant and passengers were friendly.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

We were happy with our experience. The price for tickets was much less than Delta and we actually took off and landed a little ahead of scheduled times.

Seat back entertainment monitors would be nice. We did enjoy the In-Flight WiFi.

Our flight schedule was changed over six times, ultimately leaving us with a layover much shorter than we originally booked, which meant a panicked run through the airport. And the entertainment screen didn't function. As I've come to expect with Delta, a very mediocre and not customer-focused experience. This is on top of an outbound flight that was so delayed by mechanical issues, we had to spend the night at our layover city.

Staff were courteous and helpful. The only negative was the flight delays (which are usually unavoidable) and the high baggage price.

Absolutely terrible, from the customer service to boarding the plane. On the phone, there was some mishaps with getting in my correct date and they did not help me retrieve a refund or any assistance. I’m gonna be reporting to all my followers and family around the region of Los Angeles to New York.

Could not fly out of Canada. Called airlines on Monday, July 14th. Tried to cancel the flight 7 days away, but they said I could not cancel and there would be no refund.

A little disorganized but overall good. The Delta flights were great though

Biggest problem for me is that I am Star Alliance Gold and they were not able to give me access to to Maple Lounge because of some computer glitch . It was management by information system. She could clearly see my status and still would not give me access because the computer woudl not let her. She should have override that be attentive to a customer and figure rhat out later

Economy seats always cramped, no meal on international flight, no plugs for electronics, but we got there and cabin crew was excellent.

Horrible, experience, 5 hours delay, they changed gates 3 times, the last one we had to wait for 1::30 hre for the door to open to get to that gate. 0 apologies from Air Canada, they don’t care at all about their passengers

I paid for comfort plus seats but did not get the extra leg room. When I told the stewardess, she just ignored me.

Great breakfast and coffee …..fastest bag service I have ever had in NOLA

I had a very disappointing experience with customer service. I was suffering from a severe viral infection that included a rash and persistent cough, leaving me unable to even sit upright. Given the circumstances, I requested travel credits from Canada Air, explaining the potential health risk to others onboard. However, the airline showed no concern for my condition and stated they were not in a position to make decisions based on health considerations. Despite my illness, I received no support or flexibility. Ultimately, I chose to forgo my flight due to their lack of responsiveness. It’s unfortunate that airlines like this operate without prioritizing passenger health and safety.

Late departing. Late arriving. More worried about limiting bags on board. Free beer and wine a nice surprise.

I did not noticed baggage was separate - I had assumed international flights included luggage, so it surprised me I had to pay to check a bag.

Flight got delayed for no reason. And Air Canada was doing 3 boardings via the same gate. It was chaotic!

My return flight experience was one of the worst times I have had traveling anywhere this year. Not because of the flight. It was because there was not enough time allocated to deplane, go through U.S. Customs and U.S. Security to get to the gate for the connecting flight to Boston which I missed, There was well less than an hour between my landing in Montreal from Prince Edward Island to my connecting gate. I even called Air Canada on the morning of my return and noted my concern over the short layover time, not more that 45 minutes. The initial flight was four minutes late. I was seated in the rear of the first aircraft, and it took at least 20 minutes to deplane. The U.S. Customs was a considerable distance from the gate at which we landed. The need for double security seemed unnecessary and redundant. The distance from the security to my gate was again fairly great, and the wrong gate number was listed on my boarding pass. The agent I approached at the flight that was going to Newark, New Jersey was too busy to answer my question as to what gate was for Boston. When I got to the right gate, they had just closed the door to the aircraft even though I arrived a minute late. If I knew the distance to Customs and from Security to the gate, I would have asked for a seat on the next available flight which was 4:30 pm. When I made my call at 6:00AM that morning. When I asked the agent at the Boston gate, he said that the 4:30 flight was already “OVERBOOKED!” I was put on an 8:30 PM flight and didn’t get home until MIDNIGHT. I then had to care for a barnful of hungry animals and didn’t get to bed until 2:00 AM.

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

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