PDX - YWG

C$ 530 Find Cheap Flights from Portland to Winnipeg

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Winnipeg departing on 12/1. 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
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Everything you should know

Cheapest round-trip
C$ 530
United Airlines
Mon 12/1Thu 15/1
PDX - YWG • 1 stop
Cheapest one-way flights
Multiple Airlines
Sun 14/12
PDX - YWG • multi-stop
Top airlines
United Airlines
Cheapest • from C$ 530 (round-trip)
WestJet
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+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 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

Mon, 12 Jan - Thu, 15 Jan
United Airlines Logo
11:59 p.m. - 11:57 a.m.
PDX
-
YWG
9h 58m1 stop
United Airlines Logo
2:20 p.m. - 10:32 p.m.
YWG
-
PDX
10h 12m1 stop
C$ 530United Airlines
Mon, 12 Jan - Thu, 15 Jan
United Airlines Logo
1:24 p.m. - 11:57 a.m.
PDX
-
YWG
20h 33m2 stops
United Airlines Logo
2:20 p.m. - 10:32 p.m.
YWG
-
PDX
10h 12m1 stop
C$ 537United Airlines
Mon, 12 Jan - Thu, 15 Jan
Air Canada Logo
9:50 a.m. - 6:09 p.m.
PDX
-
YWG
6h 19m1 stop
Air Canada Logo
10:45 a.m. - 2:40 p.m.
YWG
-
PDX
5h 55m1 stop
C$ 574Air Canada
Mon, 12 Jan - Thu, 15 Jan
Air Canada Logo
9:50 a.m. - 6:09 p.m.
PDX
-
YWG
6h 19m1 stop
Air Canada Logo
10:45 a.m. - 2:40 p.m.
YWG
-
PDX
5h 55m1 stop
C$ 576Air Canada
Mon, 12 Jan - Thu, 15 Jan
United Airlines Logo
1:24 p.m. - 11:57 a.m.
PDX
-
YWG
20h 33m2 stops
United Airlines Logo
2:20 p.m. - 10:32 p.m.
YWG
-
PDX
10h 12m1 stop
C$ 602United Airlines
Mon, 12 Jan - Thu, 15 Jan
Air Canada Logo
7:45 a.m. - 9:04 p.m.
PDX
-
YWG
11h 19m2 stops
Air Canada Logo
8:00 a.m. - 6:30 p.m.
YWG
-
PDX
12h 30m2 stops
C$ 735Air Canada
Thu, 25 Dec - Mon, 29 Dec
United Airlines Logo
12:54 p.m. - 8:51 p.m.
PDX
-
YWG
5h 57m1 stop
United Airlines Logo
8:40 a.m. - 10:59 p.m.
YWG
-
PDX
16h 19m1 stop
C$ 987United Airlines
Thu, 25 Dec - Mon, 29 Dec
United Airlines Logo
7:30 a.m. - 11:57 a.m.
PDX
-
YWG
26h 27m2 stops
United Airlines Logo
8:40 a.m. - 10:59 p.m.
YWG
-
PDX
16h 19m1 stop
C$ 1,001United Airlines
Thu, 25 Dec - Mon, 29 Dec
WestJet Logo
12:29 p.m. - 10:41 p.m.
PDX
-
YWG
8h 12m2 stops
WestJet Logo
5:55 a.m. - 11:05 a.m.
YWG
-
PDX
31h 10m2 stops
C$ 1,126WestJet
Thu, 25 Dec - Mon, 29 Dec
American Airlines Logo
10:21 p.m. - 11:35 p.m.
PDX
-
YWG
23h 14m2 stops
American Airlines Logo
6:00 a.m. - 8:54 p.m.
YWG
-
PDX
16h 54m3 stops
C$ 2,072American 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.

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

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

What’s the cheapest day of the week to fly from Portland to Winnipeg?

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

When flying from Portland to Winnipeg, you should consider leaving on a Thursday and avoid Fridays if you are looking for the best rates. For your return to Portland, you’ll find the best rates on Sundays and the most expensive ones on Mondays.

Good to know

Low seasonFebruary
Cheapest flightC$ 530
Best time to beat the crowds (48% less expensive on average)
Most popular time to fly and prices are also 5% 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 C$ 530 for a round-trip ticket.

  • Which airports will I be using when flying from Portland to Winnipeg?

    When flying out of Portland you will be using Portland. You will be landing at Winnipeg, also known as Winnipeg.

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

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

  • 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.

  • 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 airline flying 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.
7.2
WestJetOverall score based on 3201 reviews
6.1Entertainment
7.1Comfort
6.2Food
7.9Crew
7.4Boarding
Airline reviews

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

6.0 GoodAnonymous, Dec 2025
ATL - YYC
Read more WestJet reviews

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

When flying premium on a two our flight a light lunch would have been nice considering the price you pay. A Kit Kat bar and bag of chips is rather cheap service.

What do you expect from a Dash 8 plane? No seats really comfortable.

my wife got very sick and we did not travel . we booked and bought the travel insurance and dot nothing but hassle and a triangle of stress in trying to make the insurance claim I called in and was told they would not give me anything in writing to say they would not refund my money back this make it impossible to file the claim I will never book with Kayak again.

We got delayed to the point of having a 20 hour layover. That is absurd. I couldn’t believe it. I’m furious.

Kayak was the problem! The tickets we bought did not allow for carry on or checked luggage and we ended up paying more for those services than the tickets! The paperwork Kayak provided for the receipt left the luggage policy for Westair intentionally blank. This was intentionally decietful on Kayak's part. Our additional cost was over $400.00! I will be calling customer service today asking for refunds and I will keep you informed on any review sites as I can. Keith

Leaving the same day as planned would've been better

I like the web site, prompt notifications, website checks in process, and airport check in. The flight attendants are attentive and polite. The return flight was 2 hours late and reason vine doesn't sound like an unplanned and unexpected issue (scheduled plane maintenance).

Our flight was delayed almost 3.5 hours (some of the issue seemed to be weather-related, yes) but NOTHING was offered as an conciliatory gesture for this delay. No food offering or any additional drink offering. There is no entertainment is available on any screen behind the seats. The airlines are so quick to penalize customers for slightest requests for comfort- seat changes, complicated baggage allowances, seating zones which are utterly dehumanizing (ZONE 9? after Zone 4- why? This is so clearly meant to be a message to those that do not have 'loyalty' to this airline to make a distinguishing line in the sand. There is such a lack of humanity in the way people are corralled in and spoken to. So, I don't think airlines should be all that surprised when those some dehumanizing corporate treatment is returned to them when asked. The flight on the way into Calgary was scheduled to arrived at 9:25 and we arrived at 12:45 AM. It is not okay. I would think TWICE and possibly once more before booking with them again. Their overhead bins are small and limited so they bully you into either paying for a $90 checked bag or gate check a lot of people's bags. Often on their website there is no carry-on bag allowance. Beware!

everything was fine expect massive delays - not the airline’s fault

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

Information on your arrival and departure airports