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Cheap flights from Winnipeg to Portland from C$ 239

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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
26 Nov — 3 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Portland (PDX). 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 27 October 2025.

Round-trip from

C$ 470

One-way from

C$ 239

Popular in

June

Cheapest in

July

Average price

C$ 570
Air Canada
  • Air Canada
  • 11/12-18/12
  • 2 total stops
  • 13h 54m total
  • Winnipeg to Portland
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11/12
  • 11/12
  • 3 total stops
  • 25h 16m total
  • Winnipeg to Portland
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Winnipeg to Portland

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Portland
Explore the most affordable flight options available from Winnipeg to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 27 October 2025.

Thu 11/1210:45 a.m.YWG - PDX
1 stop5h 55mAir Canada
Thu 18/123:15 p.m.PDX - YWG
1 stop7h 59mAir Canada
Deal found 27/10C$ 470
Thu 18/1210:45 a.m.YWG - PDX
1 stop5h 55mAir Canada
Thu 1/13:15 p.m.PDX - YWG
1 stop7h 59mAir Canada
Deal found 26/10C$ 480
Wed 24/129:40 p.m.YWG - PDX
1 stop13h 35mAir Canada
Sun 28/123:15 p.m.PDX - YWG
1 stop7h 59mAir Canada
Deal found 27/10C$ 495
Thu 11/1212:35 p.m.YWG - PDX
2 stops12h 05mDelta
Wed 17/1212:32 a.m.PDX - YWG
1 stop9h 13mDelta
Deal found 27/10C$ 536
Wed 24/1212:35 p.m.YWG - PDX
1 stop9h 59mDelta
Sun 28/127:30 p.m.PDX - YWG
2 stops14h 15mDelta
Deal found 27/10C$ 592
Thu 18/1210:55 a.m.YWG - PDX
2 stops27h 59mWestJet
Thu 1/12:11 p.m.PDX - YWG
2 stops27h 55mWestJet
Deal found 26/10C$ 700

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Portland 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 629,999 searches. Data last updated 27 October 2025.
Use the filters below to find and compare flights from Winnipeg to Portland that are best for you.

Fly from

Winnipeg

Fly to

Portland

Route

Depart

Return

Price

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 11/12

10:45 a.m.-2:40 p.m.

1 stop5h 55m

Portland

Thu 18/12

3:15 p.m.-1:14 a.m.

1 stop7h 59m

C$ 470

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 18/12

10:45 a.m.-2:40 p.m.

1 stop5h 55m

Portland

Thu 1/1

3:15 p.m.-1:14 a.m.

1 stop7h 59m

C$ 480

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 4/3

10:45 a.m.-2:40 p.m.

1 stop5h 55m

Portland

Thu 5/3

9:50 a.m.-6:09 p.m.

1 stop6h 19m

C$ 480

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 24/12

9:40 p.m.-9:15 a.m.

1 stop13h 35m

Portland

Sun 28/12

3:15 p.m.-1:14 a.m.

1 stop7h 59m

C$ 495

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 11/12

12:40 p.m.-11:56 a.m.

3 stops25h 16m

C$ 239

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 8/12

10:45 a.m.-2:40 p.m.

1 stop5h 55m

C$ 269

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 8/12

12:35 p.m.-10:40 p.m.

2 stops12h 05m

C$ 283

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 8/12

7:05 a.m.-12:12 p.m.

3 stops31h 07m

C$ 668

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 8/12

6:00 a.m.-11:23 p.m.

3 stops19h 23m

C$ 709

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/10

Best time to book a flight from Winnipeg to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Winnipeg 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 Winnipeg to Portland

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

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Portland (average of C$ 199). Flying from Winnipeg to Portland in December is currently the most expensive (average of C$ 455). 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 YWG to PDX?

Find hourly flight availability from Winnipeg to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 27 October 2025.

It’s typically best to fly out from Winnipeg to Portland in the evening. Doing so could potentially save you 48% on the flight price compared to flying at noon, which is usually more expensive.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated 27 October 2025.
Get a feel of what it's like to fly with United Airlines,WestJet, andAir Canada from Winnipeg to Portland by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,997 reviews
Check prices

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews
Check prices

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
WestJet
7.2
Good
3,148 reviews
United Airlines
7.4
Good
8,997 reviews
Check prices

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Air Canada
7.1
Good
10,370 reviews
United Airlines
7.4
Good
8,997 reviews
Check prices

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Portland. 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 Winnipeg to Portland?

    There are many flights that can get you from Winnipeg to Portland in 5h 55m. Fly via Air Canada to get the fastest option. The distance between Winnipeg and Portland is about 1944 km.

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

    According to our current data, WestJet (C$ 231), United Airlines (C$ 310), and Air Canada (C$ 327) offers the cheapest pricing from Winnipeg to Portland. You may be able to fly from Winnipeg to Portland for 52% less than the average price by searching for these airlines.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Portland 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 Winnipeg to Portland?

    Currently, August is the cheapest month in which you can book a flight from Winnipeg to Portland (average of C$ 199). Flying from Winnipeg to Portland in December is currently the most expensive (average of C$ 455). 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

Travelling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Tillamook
Cannon Beach
Lincoln City

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Winnipeg to Portland

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Medford flights

Top 3 airlines flying from Winnipeg to Portland

Discover the top 3 airlines that operate flights from Winnipeg to Portland. 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 629,999 searches. Data last updated 27 October 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 231AverageC$ 447FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 310AverageC$ 426FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 327AverageC$ 449FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Portland?

Deals for Winnipeg to Portland flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Portland?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Winnipeg to Portland for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Winnipeg to Portland with no change fees?

Certainly. Search results for flights to Portland from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Winnipeg to Portland become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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