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$280+ Cheap flights from Portland (PDX) to Winnipeg (YWG)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Feb 6 — Feb 131
Fri 2/6
Fri 2/13
1 adult, Economy
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Cheap 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 January 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$259
(Air Canada)

Popular in

December

Cheapest in

February
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
Highest demand for flights based on searches. 22% potential increase in price ($94 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($28 potential savings vs. average RT price).
Search Deals

Find 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 January 7, 2026.

This Air Canada deal was found by Cheapflights users on 1/6. 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.
Thu 5/143:25 pmPDX - YWG
1 stop8h 34mAir Canada
Mon 5/255:45 amYWG - PDX
1 stop5h 45mAir Canada
Deal found 1/6$280
This Delta deal was found by Cheapflights users on 1/7. 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.
Wed 3/1112:30 amPDX - YWG
1 stop9h 30mDelta
Mon 3/1612:50 pmYWG - PDX
1 stop10h 22mDelta
Deal found 1/7$282
This Air Canada deal was found by Cheapflights users on 1/7. 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.
Wed 3/183:15 pmPDX - YWG
1 stop7h 59mAir Canada
Thu 3/266:00 amYWG - PDX
1 stop14h 30mAir Canada
Deal found 1/7$287
This United Airlines deal was found by Cheapflights users on 1/7. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1211:59 pmPDX - YWG
1 stop9h 58mUnited Airlines
Mon 3/162:20 pmYWG - PDX
2 stops21h 34mUnited Airlines
Deal found 1/7$292
This Air Canada deal was found by Cheapflights users on 1/7. 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.
Thu 2/193:15 pmPDX - YWG
1 stop7h 59mAir Canada
Sun 2/226:00 amYWG - PDX
1 stop10h 40mAir Canada
Deal found 1/7$304
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/137:05 amPDX - YWG
2 stops13h 35mMultiple Airlines
Sun 3/154:55 pmYWG - PDX
1 stop18h 03mMultiple Airlines
Deal found 1/7$310
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:46 pmPDX - YWG
2 stops19h 54mMultiple Airlines
Mon 5/258:15 pmYWG - PDX
1 stop15h 33mMultiple Airlines
Deal found 1/6$318
This Air Canada deal was found by Cheapflights users on 1/6. 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.
Wed 2/43:15 pmPDX - YWG
1 stop7h 59mAir Canada
Wed 2/1110:40 amYWG - PDX
1 stop6h 00mAir Canada
Deal found 1/6$332
This United Airlines deal was found by Cheapflights users on 1/6. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2011:59 pmPDX - YWG
1 stop9h 58mUnited Airlines
Fri 2/272:20 pmYWG - PDX
2 stops21h 22mUnited Airlines
Deal found 1/6$348
This Air Canada deal was found by Cheapflights users on 1/6. 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.
Thu 2/53:15 pmPDX - YWG
1 stop7h 59mAir Canada
Thu 2/126:00 amYWG - PDX
1 stop14h 30mAir Canada
Deal found 1/6$351

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 January 7, 2026.
Use the filters below to find and compare flights from Portland to Winnipeg that are best for you.

Fly from

Portland

Fly to

Winnipeg

Route

Depart

Return

Price

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 3/11

12:30 am-12:00 pm

1 stop9h 30m

Winnipeg

Mon 3/16

12:50 pm-9:12 pm

1 stop10h 22m

$282

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 3/18

3:15 pm-1:14 am

1 stop7h 59m

Winnipeg

Thu 3/26

6:00 am-6:30 pm

1 stop14h 30m

$287

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 3/12

11:59 pm-11:57 am

1 stop9h 58m

Winnipeg

Mon 3/16

2:20 pm-9:54 am

2 stops21h 34m

$292

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 2/19

3:15 pm-1:14 am

1 stop7h 59m

Winnipeg

Sun 2/22

6:00 am-2:40 pm

1 stop10h 40m

$304

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 3/13

7:05 am-10:40 pm

2 stops13h 35m

Winnipeg

Sun 3/15

4:55 pm-8:58 am

1 stop18h 03m

$310

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 5/14

7:46 pm-5:40 pm

2 stops19h 54m

Winnipeg

Mon 5/25

8:15 pm-9:48 am

1 stop15h 33m

$318

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 2/4

3:15 pm-1:14 am

1 stop7h 59m

Winnipeg

Wed 2/11

10:40 am-2:40 pm

1 stop6h 00m

$332

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 2/20

11:59 pm-11:57 am

1 stop9h 58m

Winnipeg

Fri 2/27

2:20 pm-9:42 am

2 stops21h 22m

$348

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Thu 2/5

3:15 pm-1:14 am

1 stop7h 59m

Winnipeg

Thu 2/12

6:00 am-6:30 pm

1 stop14h 30m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Expedia the most. Expedia 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.

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 January 7, 2026.
Read reviews from past customers who have flown Delta, WestJet, and Air 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
7.9
Good
8,021 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.8

Crew

8.5

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,021 reviews
Delta
7.9
Good
8,021 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.8

Crew

8.5

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
WestJet
7.2
Good
3,235 reviews
Delta
7.9
Good
8,021 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.8

Crew

8.5

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Air Canada
7.1
Good
10,600 reviews
Delta
7.9
Good
8,021 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.8

Crew

8.5

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 14m. 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 WestJet. Our recent data shows that you can find tickets from as low as $88 on this airline. Additional options worth looking into are Delta and Air Canada, starting at $143 and $163 round-trip. You may be able to fly from Portland to Winnipeg for 73% 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.

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 January 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$150Average$341FlexibilityNo cancel feeOn-time60%
DeltaCheapest$160Average$472FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$175Average$327FlexibilityNo cancel feeOn-time67%

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