YWG - PDX

C$ 305 Find Cheap Flights from Winnipeg to Portland

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Portland departing on 13/5. 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.
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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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Cheap Flight Deals 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.

Recent round-trip flight deals from Winnipeg to Portland

KAYAK's recommended round-trip deals from the most popular airlines that fly from Winnipeg to Portland.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Air Canada Logo
5:20 a.m. - 9:30 a.m.YWG-PDX
6h 10m1 stop
Air Canada Logo
8:30 a.m. - 10:33 p.m.PDX-YWG
12h 03m1 stop
C$ 305Air Canada
Find Deal
Tue, 13 May - Wed, 28 May
United Airlines Logo
4:25 p.m. - 9:06 p.m.YWG-PDX
6h 41m1 stop
United Airlines Logo
4:15 p.m. - 3:31 p.m.PDX-YWG
21h 16m2 stops
C$ 334United Airlines
Find Deal
Tue, 13 May - Wed, 28 May
Delta Logo
12:26 p.m. - 8:23 p.m.YWG-PDX
9h 57m1 stop
Delta Logo
8:02 p.m. - 11:36 a.m.PDX-YWG
13h 34m2 stops
C$ 356Delta
Find Deal
Fri, 13 Jun - Mon, 16 Jun
WestJet Logo
9:05 p.m. - 1:05 p.m.YWG-PDX
18h 00m1 stop
WestJet Logo
1:45 p.m. - 5:28 p.m.PDX-YWG
25h 43m2 stops
C$ 357WestJet
Find Deal
Fri, 16 May - Mon, 19 May
WestJet Logo
6:30 a.m. - 1:05 p.m.YWG-PDX
32h 35m2 stops
WestJet Logo
1:45 p.m. - 11:28 a.m.PDX-YWG
19h 43m2 stops
C$ 402WestJet
Find Deal
Fri, 16 May - Mon, 19 May
 Logo
9:05 p.m. - 1:05 p.m.YWG-PDX
18h 00m1 stop
 Logo
4:42 p.m. - 8:19 p.m.PDX-YWG
25h 37m2 stops
C$ 425
Find Deal
Fri, 16 May - Mon, 19 May
 Logo
9:05 p.m. - 1:05 p.m.YWG-PDX
18h 00m1 stop
 Logo
9:45 p.m. - 2:30 p.m.PDX-YWG
14h 45m2 stops
C$ 463
Find Deal
Fri, 16 May - Mon, 19 May
Air Canada Logo
5:35 a.m. - 9:20 a.m.YWG-PDX
5h 45m1 stop
Air Canada Logo
7:40 p.m. - 12:55 p.m.PDX-YWG
15h 15m1 stop
C$ 489Air Canada
Find Deal
Fri, 13 Jun - Mon, 16 Jun
Delta Logo
8:30 a.m. - 12:52 p.m.YWG-PDX
6h 22m1 stop
Delta Logo
12:40 a.m. - 11:57 a.m.PDX-YWG
9h 17m1 stop
C$ 505Delta
Find Deal
Mon, 12 May - Thu, 15 May
United Airlines Logo
4:25 p.m. - 12:31 a.m.YWG-PDX
10h 06m2 stops
United Airlines Logo
3:56 p.m. - 3:31 p.m.PDX-YWG
21h 35m2 stops
C$ 613United Airlines
Find Deal
Fri, 16 May - Mon, 19 May

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$ 316 (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$ 559 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low season

January

High season

August

Cheapest flight

C$ 305
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly and prices are also 30% 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$ 220 for a round-trip ticket.

  • 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, and SkyTeam are the airline alliances operating flights between Winnipeg and Portland, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Winnipeg to Portland, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Portland are Delta and United Airlines. With an average price for the route of C$ 404 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of C$ 410 and an overall rating of 7.4.

  • 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.

See more FAQs

Top 4 airlines serving 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 7920 reviews
8.2Boarding
7.9Entertainment
7.9Comfort
8.5Crew
7.3Food
Airline reviews

Delta flight was on time, seats were comfortable, and crew was nice.

8.0 ExcellentAnonymous, Apr 2025LAX - DEN
Read more Delta reviews

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

I love the free WiFi!! Crew was nice. Bathroom was decent. First time flying delta in a long time and I enjoyed it. Will definitely look into booking with Delta more but I think Delta is a little more expensive than the other airlines.

third trip overseas with delta recently where the TV did not work- not acceptable for a 8 hour flight! your food really has declined crew great and I am loyal to delta

Boarding in Amsterdam is always chaotic. KLM/ Delta has not streamlined or made it efficient as it was boarding in Detroit . The food was mediocre The crew was unfriendly and more focused on getting things done quickly rather than service with a smile .

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.

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

headphone jack didnt work for the first flight and not much variety

Pilot Erika DeLong made us feel safe and at ease in a frankly scary time to be flying. Her warm smile and greeting and excellent command of the aircraft in foggy bumpy weather helped us all to calm our nerves and get us home safely.

Plane 3 hours late. Missed connection. No help from gate staff. App horrible. Lost connection repeatedly. No service desk. Finally got help from young girl driving cart.

Not as good as expected Air Can needs to improve totally rated on internet as worst

The flight was delayed, it took longer than anticipated because of weather, and they broke my luggage.

Everything was good. Flight was on time, luggage pickup was quick. The staff were great. Could not ask for anything more.

Internet on both flights was sketchy. Thus in flight entertainment was non- existent on MN - Balrimote leg.

It took 30 minutes to check in with the Westjet rep. They didn’t have enough seats and she needed to make a call… I am always “randomly” selected to be checked at security. Their “randomly “ selection system may need some updating. They treat people like criminals. It is not appropriate behavior.

Will never book through you again. Very disappointed in the notices and action taken or provided when planes are rescheduled, enough to cause missed connections

Lost my luggage. Filed a report and there is no response. Received a phone call from another airline that said they had the bag and they did not know what to do with it

Very good over all , would have been nice to have entertainment on the flight

Absolutely the worst airline I have ever taken. They lost my baggage and told me my bag tags had been cancelled. When my bags arrived days later I had to pick them up at 3:15 am. My return flight was delayed another 6 hours and they broke my bag. Westjet does nothing to try and make it a better customer experience and all the customers services representatives I spoke with were useless and incompetent. Never flying westjet again.

it's all good nothing you can do make better 😌

It was an awesome experience flying with Westjet. This was my first domestic flight experience in Canada.

Very old planes. Seats were not comfortable. Air was not on during the flight leading to incredibly stuffy conditions.

It was so bad experience they wanted just charged passengers for any reason.

Overall good experience. The flight from Toronto to Denver does not have entertainment - movies to watch.

There is not enough space between two chairs and raws.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

It was a lovely flight. Very attentive crew, comfortable seats, good food and entertainment. Highly recommended. Only difficulty was with their app.

Terrible. Flight was delayed for hours and we ended up arriving at our home at 4am after 20+ hours flying.

Flight was cancelled around 45 -1hr minutes before scheduled take off time due to mechanical issues we hadn’t even boarded yet. Had to reroute to Orlando so someone had to drive 2 1/2 to come and get me… the alternative was go through Toronto and get a later flight which didn’t work for my schedule. The flight attendants barely gave anyone a smile…not the same as flying when a client/passenger was important. Very disappointed. By the way I have never ever made a complaint online about any company with feedback…even when I probably should have. The only good experience was the boarding desk associates who were very professional and got me on another flight with my checked bags…very nice team.

Flight delay, cancellation rescheduling and misdirected luggage which created some stress. It all worked out in the end.

Actually as my experience with air Canada from Canada to Newark it was crazy for me because it was a lot of delays which for me it shouldn’t be like that, but I was able to coup with it so that was my experience I hope next time they will do good on that thanks.

Boarding was challenging as we had to use the stairs from the tarmac. Stairs are okay but a roller bag makes it challenging.

Ensure prepaid food arrangements are appropriately understood by flight crew of who purchased and who did not

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

Information on your arrival and departure airports

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