YWG - PDX

$184 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 1/30. 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 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$300
Overall average: $397
Multiple Airlines
Mon 1/26Sun 2/1
YWG - PDX • 1 stop
Cheapest one-way
$184
Typical prices: $188-$204
Multiple Airlines
Fri 1/30
YWG - PDX • 2 stops
When to travel
August
Cheapest • 25% price drop
February
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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 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

Mon, Jan 26 - Sun, Feb 1
Multiple Airlines Logo
4:55 pm - 9:37 am
YWG
-
PDX
18h 42m1 stop
Multiple Airlines Logo
11:09 am - 1:52 pm
PDX
-
YWG
24h 43m2 stops
$300Multiple Airlines
Mon, Jan 26 - Sun, Feb 1
Multiple Airlines Logo
4:55 pm - 9:37 am
YWG
-
PDX
18h 42m1 stop
Multiple Airlines Logo
11:09 am - 11:32 am
PDX
-
YWG
22h 23m2 stops
$320Multiple Airlines
Mon, Jan 26 - Thu, Jan 29
Multiple Airlines Logo
4:55 pm - 11:52 pm
YWG
-
PDX
8h 57m1 stop
Multiple Airlines Logo
11:28 am - 1:52 pm
PDX
-
YWG
24h 24m2 stops
$321Multiple Airlines
Tue, Mar 3 - Fri, Mar 6
Delta Logo
6:40 am - 6:48 pm
YWG
-
PDX
14h 08m2 stops
Delta Logo
12:40 am - 11:01 am
PDX
-
YWG
8h 21m1 stop
$323Delta
Mon, Jan 26 - Sun, Feb 1
Multiple Airlines Logo
4:55 pm - 9:37 am
YWG
-
PDX
18h 42m1 stop
Multiple Airlines Logo
11:09 am - 3:42 pm
PDX
-
YWG
26h 33m1 stop
$330Multiple Airlines
Mon, Apr 20 - Sat, Apr 25
United Airlines Logo
2:15 pm - 10:10 pm
YWG
-
PDX
9h 55m1 stop
United Airlines Logo
7:42 pm - 11:39 am
PDX
-
YWG
13h 57m2 stops
$335United Airlines
Mon, Jan 26 - Sat, Jan 31
Multiple Airlines Logo
4:55 pm - 9:37 am
YWG
-
PDX
18h 42m1 stop
Multiple Airlines Logo
7:38 pm - 12:41 am
PDX
-
YWG
27h 03m2 stops
$338Multiple Airlines
Sun, Mar 1 - Tue, Mar 3
Delta Logo
11:53 am - 8:30 pm
YWG
-
PDX
10h 37m1 stop
Delta Logo
12:40 am - 11:01 am
PDX
-
YWG
8h 21m1 stop
$344Delta
Sun, Mar 1 - Tue, Mar 3
Delta Logo
11:53 am - 8:31 am
YWG
-
PDX
22h 38m2 stops
Delta Logo
12:40 am - 11:01 am
PDX
-
YWG
8h 21m1 stop
$346Delta
Mon, Jan 26 - Thu, Jan 29
Air Canada Logo
10:45 am - 2:40 pm
YWG
-
PDX
5h 55m1 stop
Air Canada Logo
3:15 pm - 1:14 am
PDX
-
YWG
7h 59m1 stop
$348Air 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.

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 Thursday and more expensive on a Saturday. On your return trip to Winnipeg, you should consider flying back on a Friday, and avoid Sundays 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 $261 (return) on average. On the other hand, the most expensive months are June and October, where the average cost of round-trip tickets is $429 and $407 respectively.

Good to know

Low seasonNovember
Cheapest flight$184
Most popular time to fly and prices are also 14% 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 $184 for a one-way ticket and $300 for a round-trip.

  • Do I need a passport to fly between Winnipeg and Portland?

    Yes

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

    On your way to Portland, you’ll fly out from Winnipeg. You’ll be landing at Portland.

  • 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. Booking your flights between Winnipeg and PDX 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 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 10534 reviews
6.3Food
6.8Entertainment
7.8Crew
7.1Comfort
7.3Boarding
Airline reviews

My seat was covered in vomit and I will be reaching out to Air Canada

2.0 MediocreAnonymous, Dec 2025
YYZ - MCO
Read more Air Canada reviews

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

Baggage delayed we had to catch our cruise without any clothes 😒

Air Canada Rouge is great. Toronto Airport is the usual nightmare

Good but need to be better with the flight times.

The staff could not have been any friendlier. Lots of usb ports on our aircraft.

The staff was great and made the long trip easy peasy!

Air Canada cancelled our flight and reschedule it 26 hours later that completely interrupted my family's long waited Japan trip, it wasn't due to natural reason such as weather but under the company's control. On the day we wasted 9 hours of our time from 6am to 3pm, including a few hours in the customer counter waiting for supervisor to handle our rescheduling. When we came to the counter for rebooking help there were at least 4 employees on the counter but we were told they were not trained to handle customer rebooking, we were also told the supervisor could come 10:30 to handle our rebooking, but she showed up more than one hour later, the end result was exactly the same so the few hours we spent waiting for her was completely wasted; We already prepaid hotel and all the tickets for the our stay in Tokyo so all of the cost for the first day is completed wasted; The $80 meal voucher issues was far less than our financial loss due to the financial cancellation, and it was not surprisingly invalid (as Your company screw up everything possible along the flight), the vouchers were supposed to last 72 hours, when we tried to used it at our lounge next day less than 24 hours from its issuing at a designated restaurant, the worker there couldn't scan the vouchers after multiple tries on all 4 vouchers issued, so we had to pay the food from our own money; For the two return flights they were also full of unfortunate events that caused bad experience and further delay and waste of our time, both flights departed late and the last leg had another significant delay of more than half an hour after touchdown, the gate was for some reason not available so we waited more than half an hour, when we got out of plane it was almost one hour later than the supposed arrival time; The gate you arranged is the farthest in Vancouver airport, also was the luggage pickup location in Seattle airport; We also called customer service for rescheduling help and after a long time wait (more than an hour) we got a call back but the CS representative was equally clueless and unhelpful. Other than a fatal crash, your company couldn't do anything right and provided the worst service possible among the tons of flights we have taken in our lives.

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

Information on your arrival and departure airports