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Winnipeg

$150+ Cheap flights from Portland (PDX) to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Aug 5 — Aug 121
Wed 8/5
Wed 8/12
1 adult, Economy
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Cheap flight deals from Portland to Winnipeg

Cheapest flights from Portland to Winnipeg
Explore the most affordable flight options available from Portland to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 6, 2026.

This Trip.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:45 pm
PDX
-
YWG
1 stop5h 17m
Multiple Airlines
Wed 7/2910:10 am
YWG
-
PDX
1 stop5h 40m
Multiple Airlines
Deal found 7/2$306
This Mytrip deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:45 pm
PDX
-
YWG
2 stops14h 32m
Air Canada
Wed 7/295:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 7/2$341
This Air Canada deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:10 am
PDX
-
YWG
1 stop5h 37m
Air Canada
Wed 9/235:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 7/1$350
This United deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/124:07 pm
PDX
-
YWG
2 stops17h 45m
Multiple Airlines
Sun 9/205:45 am
YWG
-
PDX
1 stop5h 46m
Multiple Airlines
Deal found 7/2$364
This Air Canada deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/27:45 pm
PDX
-
YWG
1 stop5h 12m
Air Canada
Sat 8/86:00 am
YWG
-
PDX
1 stop5h 31m
Air Canada
Deal found 7/3$365
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1512:35 am
PDX
-
YWG
1 stop9h 19m
Delta
Sun 8/2312:46 pm
YWG
-
PDX
1 stop9h 31m
Delta
Deal found 7/3$380
This Air Canada deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/13:30 pm
PDX
-
YWG
1 stop6h 22m
Air Canada
Mon 8/109:00 pm
YWG
-
PDX
1 stop14h 31m
Air Canada
Deal found 7/1$384
This Air Canada deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:45 pm
PDX
-
YWG
1 stop5h 12m
Air Canada
Tue 9/225:45 am
YWG
-
PDX
1 stop5h 46m
Air Canada
Deal found 7/5$393
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:33 am
PDX
-
YWG
1 stop9h 20m
Delta
Wed 7/293:59 pm
YWG
-
PDX
1 stop9h 19m
Delta
Deal found 7/2$394

Find flight deals from Portland to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$306
(Trip.com)

One-way from

$150
(Kiwi.com)

Popular in

February

Cheapest in

November

Average price

$435
Provider with most accurate pricing for Portland-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Winnipeg flights.
Search Deals
From Portland to Winnipeg
Search Deals
One-way flight from Portland to Winnipeg
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 6, 2026.
Use the filters below to find and compare flights from Portland to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 9/19

3:30 pm-11:55 pm

1 stop6h 25m

Winnipeg

Wed 9/23

7:20 am-2:46 pm

2 stops9h 26m

$355
Quickest round-trip

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 8/2

7:45 pm-2:57 am

1 stop5h 12m

Winnipeg

Sat 8/8

6:00 am-9:31 am

1 stop5h 31m

$365

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 8/12

10:10 am-5:47 pm

1 stop5h 37m

Winnipeg

Tue 8/18

6:00 am-9:31 am

1 stop5h 31m

$365

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 9/19

7:45 pm-2:57 am

1 stop5h 12m

Winnipeg

Tue 9/22

5:45 am-9:31 am

1 stop5h 46m

$393

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 8/15

12:35 am-11:54 am

1 stop9h 19m

Winnipeg

Sun 8/23

12:46 pm-8:17 pm

1 stop9h 31m

$394

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 7/25

12:33 am-11:53 am

1 stop9h 20m

Winnipeg

Wed 7/29

3:59 pm-11:18 pm

1 stop9h 19m

$394

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 9/12

4:07 pm-11:52 am

2 stops17h 45m

Winnipeg

Sun 9/20

7:20 am-7:11 pm

2 stops13h 51m

$399

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Mon 7/20

7:45 pm-12:17 pm

2 stops14h 32m

Winnipeg

Wed 7/29

7:10 pm-9:31 am

2 stops16h 21m

$399

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 9/19

8:40 am-10:33 pm

2 stops11h 53m

Winnipeg

Sat 9/26

5:45 am-9:31 am

1 stop5h 46m

$407

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 9/19

8:40 am-10:33 pm

2 stops11h 53m

Winnipeg

Wed 9/23

8:45 am-8:40 pm

2 stops13h 55m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

Compare providers for flights from Portland to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Winnipeg in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Portland-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Portland to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Portland to Winnipeg?

Currently, November is the cheapest month in which you can book a flight from Portland to Winnipeg (average of $247). Flying from Portland to Winnipeg in February is currently the most expensive (average of $878). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Portland to Winnipeg?

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated July 6, 2026.
Read reviews from past customers who have flown Delta,WestJet, andAir Canada from Portland to Winnipeg. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.8
Good
8,453 reviews

Food

7.2

Overall

7.8

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,453 reviews
Delta
7.8
Good
8,453 reviews

Food

7.2

Overall

7.8

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
WestJet
7.2
Good
3,397 reviews
Delta
7.8
Good
8,453 reviews

Food

7.2

Overall

7.8

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Air Canada
7.1
Good
11,305 reviews
Delta
7.8
Good
8,453 reviews

Food

7.2

Overall

7.8

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

Related info for your journey

Find useful and relevant information for your journey from Portland to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Portland to Winnipeg?

    Departing from Portland to Winnipeg will take you 6h 25m. There are 1208 mi between Portland and Winnipeg. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Portland to Winnipeg round-trip?

    Our cheapest airline available from Portland to Winnipeg is Air Canada. Our recent data shows that you can find tickets from as low as $184 on this airline. Additional options worth looking into are Delta and WestJet, starting at $188 and $246 round-trip. You may be able to fly from Portland to Winnipeg for 65% less than the average price by searching for these airlines.

  • Can I find deals for flights from Portland to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Portland to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Winnipeg.

  • Can I find deals for business class flights from Portland to Winnipeg?

    Yes. Cheapflights offers flight deals from Portland to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland to Winnipeg?

    Currently, November is the cheapest month in which you can book a flight from Portland to Winnipeg (average of $247). Flying from Portland to Winnipeg in February is currently the most expensive (average of $878). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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Complete your trip

Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
Winnipeg car rentals
Winnipeg Airport car rentals

Top 3 airlines flying from Portland to Winnipeg

Discover the top 3 airlines that operate flights from Portland to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$184Average$439FlexibilityNo cancel feeOn-time67%
DeltaCheapest$188Average$455FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$246Average$431FlexibilityNo cancel feeOn-time60%

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