YWG - PDX

C$ 296 Find Cheap Flights from Winnipeg to Portland – Compare and Save

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 24/8. 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

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Everything you should know

Cheapest round-trip
C$ 411
Typical prices: C$ 387-C$ 679
Air Canada
Tue 22/9Thu 24/9
YWG - PDX • 1 stop
Cheapest one-way flights
C$ 296
Typical prices: C$ 399-C$ 566
Air Canada
Mon 24/8
YWG - PDX • 1 stop
Top airlines
Air Canada
Cheapest • from C$ 411 (round-trip)
Air Canada
Best reviews • 7.1 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
Calgary (YYC)
Cheapest • Avg C$ 333 (round-trip)
Calgary (YYC)
Shortest trip • 5h 40m (one-way)
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 29% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Tue, 22 Sep - Thu, 24 Sep
Air Canada Logo
5:45 a.m. - 9:31 a.m.
YWG
-
PDX
5h 46m
1 stop
Air Canada Logo
7:45 p.m. - 2:57 a.m.
PDX
-
YWG
5h 12m
1 stop
C$ 411Air Canada
Tue, 22 Sep - Sat, 26 Sep
United Airlines Logo
7:00 a.m. - 10:52 p.m.
YWG
-
PDX
17h 52m
1 stop
United Airlines Logo
4:07 p.m. - 12:37 p.m.
PDX
-
YWG
18h 30m
2 stops
C$ 452United Airlines
Thu, 3 Sep - Tue, 8 Sep
Air Canada Logo
5:45 a.m. - 9:31 a.m.
YWG
-
PDX
5h 46m
1 stop
Air Canada Logo
7:45 p.m. - 2:57 a.m.
PDX
-
YWG
5h 12m
1 stop
C$ 458Air Canada
Tue, 22 Sep - Sat, 26 Sep
Air Canada Logo
7:20 a.m. - 2:46 p.m.
YWG
-
PDX
9h 26m
2 stops
Air Canada Logo
3:30 p.m. - 11:55 p.m.
PDX
-
YWG
6h 25m
1 stop
C$ 472Air Canada
Tue, 22 Sep - Thu, 24 Sep
United Airlines Logo
2:00 p.m. - 9:32 a.m.
YWG
-
PDX
21h 32m
2 stops
United Airlines Logo
11:30 p.m. - 12:37 p.m.
PDX
-
YWG
11h 07m
1 stop
C$ 480United Airlines
Thu, 13 Aug - Sat, 22 Aug
Delta Logo
12:46 p.m. - 8:17 p.m.
YWG
-
PDX
9h 31m
1 stop
Delta Logo
12:35 a.m. - 11:54 a.m.
PDX
-
YWG
9h 19m
1 stop
C$ 503Delta
Thu, 3 Sep - Sun, 6 Sep
Air Canada Logo
5:45 a.m. - 9:31 a.m.
YWG
-
PDX
5h 46m
1 stop
Air Canada Logo
7:45 p.m. - 2:57 a.m.
PDX
-
YWG
5h 12m
1 stop
C$ 507Air Canada
Thu, 3 Sep - Tue, 8 Sep
Multiple Airlines Logo
2:00 p.m. - 10:52 p.m.
YWG
-
PDX
10h 52m
1 stop
Multiple Airlines Logo
3:30 p.m. - 12:19 p.m.
PDX
-
YWG
18h 49m
2 stops
C$ 521Multiple Airlines
Tue, 22 Sep - Sat, 26 Sep
Air Canada Logo
7:20 a.m. - 7:11 p.m.
YWG
-
PDX
13h 51m
2 stops
Air Canada Logo
7:45 p.m. - 2:57 a.m.
PDX
-
YWG
5h 12m
1 stop
C$ 523Air Canada
Thu, 13 Aug - Sun, 23 Aug
Air Canada Logo
9:00 p.m. - 9:31 a.m.
YWG
-
PDX
14h 31m
1 stop
Air Canada Logo
7:45 p.m. - 12:17 p.m.
PDX
-
YWG
14h 32m
2 stops
C$ 532Air 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.

How much is a round-trip flight from Winnipeg to Portland?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Winnipeg to Portland departing in September.

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$ 430 (return) on average. On the other hand, the most expensive months are April and December, where the average cost of round-trip tickets is C$ 763 and C$ 759 respectively.

Find deals

Good to know

Low season

June

Cheapest flight

C$ 296
Best time to beat the crowds (24% less expensive on average)
Most popular time to fly and prices are also 8% 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 5 days, the lowest price for a flight from Winnipeg to Portland was C$ 296 for a one-way ticket and C$ 411 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.

  • 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 airline 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.
7.1
Air CanadaOverall score based on 11371 reviews
6.8Entertainment
7.3Boarding
7.8Crew
6.3Food
7.1Comfort
Airline reviews

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

10.0 ExcellentBeth, Feb 2026
YVR - PDX
Read more Air Canada reviews

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

Amazing service, with enthusiastic crew members, and some breathtaking views of Vancouver. No IFE though, as it is only a 1 hour flight on a regional Turboprop jet.

Could not understand what the attendant was saying during his announcements.

Once again our Air Canada flight was delayed! I'm hopeful competition arrives with other airlines soon and maybe they will make a better effort to be on time!

Boarding was OK. The overhead bins on the Havilland 400 are smaller than the allowable carry on bag sizes, making the bags to be jammed in and as a result slowing the boarding process.

My luggage was lost and didn't arrive on my flight

Not so good. Got seat no 12 e. Squeezed between two people. No entertainment, hard to move around. Did not enjoyed that flight.

Flight delayed, Poor communication. Uncomfortable/cramped gate area. Insistence by AC staff that our carry-on bags had to be checked due to allegedly small size of overhead bins (not true, as we saw when we boarded). Awful-tasting snacks.

There was no entertainment at our seats. The flight was comfortable and we had leg room. The snack we had was really good.

The original connecting flight from Vancouver to Portland was canceled and then delayed. I ended up waiting for almost seven hours instead of three.

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

Information on your arrival and departure airports

Winnipeg (YWG)
Portland (PDX)