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$90+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Winnipeg are usually found in February or August, booked 27 days in advance, depart on a Friday or Monday and return on a Tuesday

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 August 14, 2025.

Round-trip from

$242
(Priceline)

One-way from

$90
(Mytrip)

Popular in

May

Cheapest in

February

Average price

$260
From Portland to Winnipeg
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One-way flight from Portland to Winnipeg
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 14, 2025.

This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/131:45 pmPDX - YWG
1 stop7h 25mWestJet
Sat 9/206:30 amYWG - PDX
2 stops8h 34mWestJet
Deal found 8/14$242
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Sun 9/285:08 pmPDX - YWG
1 stop19h 05mMultiple Airlines
Sun 10/58:30 amYWG - PDX
1 stop6h 35mMultiple Airlines
Deal found 8/14$296
This Delta deal was found by Cheapflights users on 8/14. 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.
Fri 9/1212:45 amPDX - YWG
1 stop9h 09mDelta
Sat 9/2012:44 pmYWG - PDX
1 stop10h 12mDelta
Deal found 8/14$314
This Trip.com deal was found by Cheapflights users on 8/14. 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.
Wed 10/1511:07 amPDX - YWG
2 stops10h 33mMultiple Airlines
Sun 10/196:30 amYWG - PDX
2 stops10h 18mMultiple Airlines
Deal found 8/14$315
This United deal was found by Cheapflights users on 8/14. 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.
Wed 10/155:00 amPDX - YWG
1 stop6h 09mMultiple Airlines
Wed 10/157:10 pmYWG - PDX
1 stop5h 51mMultiple Airlines
Deal found 8/14$370

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 August 14, 2025.
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

Sat 9/13

1:45 pm-11:10 pm

1 stop7h 25m

Winnipeg

Sat 9/20

6:30 am-1:04 pm

2 stops8h 34m

$242

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 9/28

5:08 pm-2:13 pm

1 stop19h 05m

Winnipeg

Sun 10/5

8:30 am-1:05 pm

1 stop6h 35m

$296

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 9/12

12:45 am-11:54 am

1 stop9h 09m

Winnipeg

Sat 9/20

12:44 pm-8:56 pm

1 stop10h 12m

$314

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 10/15

11:07 am-11:40 pm

2 stops10h 33m

Winnipeg

Sun 10/19

6:30 am-2:48 pm

2 stops10h 18m

$315

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Wed 10/15

5:00 am-1:09 pm

1 stop6h 09m

Winnipeg

Wed 10/15

7:10 pm-11:01 pm

1 stop5h 51m

$370

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sun 10/5

1:45 pm-9:30 pm

1 stop5h 45m

$90

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 9/13

1:45 pm-9:30 pm

1 stop5h 45m

$93

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 9/12

12:45 am-11:54 am

1 stop9h 09m

$149

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Fri 11/21

3:15 pm-1:09 am

1 stop7h 54m

$159

PortlandWinnipeg

PDX - YWG

PDXYWG

Portland

Sat 9/13

1:45 pm-1:09 pm

2 stops21h 24m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 15 results
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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

How far ahead should I book a flight from Portland to Winnipeg?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Winnipeg. Price data was last updated on August 8, 2025.

Booking 27 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Winnipeg. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, August is the cheapest month in which you can book a flight from Portland to Winnipeg (average of $358). Flying from Portland to Winnipeg in December is currently the most expensive (average of $495). 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.

What is the cheapest time of day to fly from PDX to YWG?

Find hourly flight availability from Portland to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

A simple way to save on the total cost of your ticket is to fly from Portland to Winnipeg in the afternoon. If you’re flexible enough to do this you can expect to save up to 21% on your trip compared to booking a flight in the evening.

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 August 14, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and WestJet 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
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,916 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
3,015 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,949 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

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

    Our cheapest airline available from Portland to Winnipeg is Delta. Our recent data shows that you can find tickets from as low as $143 on this airline. Additional options worth looking into are WestJet and Air Canada, starting at $150 and $175 round-trip. You may be able to fly from Portland to Winnipeg for 57% 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, August is the cheapest month in which you can book a flight from Portland to Winnipeg (average of $358). Flying from Portland to Winnipeg in December is currently the most expensive (average of $495). 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 4 airlines flying from Portland to Winnipeg

Discover the top 4 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$143Average$472FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$150Average$310FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$175Average$350FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$211Average$317FlexibilityNo cancel feeOn-time69%

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