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Cheap flights from Winnipeg to Portland from C$ 251

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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
26 Aug — 2 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap 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 July 2026.

Wed 19/812:46 p.m.
YWG
-
PDX
1 stop9h 31m
Delta
Sat 22/812:35 a.m.
PDX
-
YWG
1 stop9h 19m
Delta
Deal found 23/7C$ 400
Thu 20/83:58 p.m.
YWG
-
PDX
1 stop9h 22m
Delta
Mon 24/812:35 a.m.
PDX
-
YWG
1 stop9h 19m
Delta
Deal found 23/7C$ 459
Tue 22/93:58 p.m.
YWG
-
PDX
1 stop6h 18m
Delta
Fri 25/912:25 a.m.
PDX
-
YWG
1 stop9h 26m
Delta
Deal found 22/7C$ 461
Tue 22/95:45 a.m.
YWG
-
PDX
1 stop5h 46m
Air Canada
Sat 26/93:30 p.m.
PDX
-
YWG
1 stop6h 25m
Air Canada
Deal found 25/7C$ 480
Tue 22/97:00 a.m.
YWG
-
PDX
2 stops16h 05m
United Airlines
Sat 26/98:30 a.m.
PDX
-
YWG
1 stop12h 03m
United Airlines
Deal found 26/7C$ 488
Wed 19/812:46 p.m.
YWG
-
PDX
1 stop9h 31m
Delta
Tue 25/86:00 a.m.
PDX
-
YWG
1 stop7h 08m
Delta
Deal found 23/7C$ 500
Fri 7/83:58 p.m.
YWG
-
PDX
1 stop9h 22m
Delta
Mon 10/812:35 a.m.
PDX
-
YWG
1 stop9h 19m
Delta
Deal found 23/7C$ 511
Tue 18/89:00 p.m.
YWG
-
PDX
1 stop14h 31m
Air Canada
Tue 25/87:45 p.m.
PDX
-
YWG
1 stop5h 12m
Air Canada
Deal found 23/7C$ 524
Thu 3/95:45 a.m.
YWG
-
PDX
1 stop5h 46m
Air Canada
Sun 6/97:45 p.m.
PDX
-
YWG
1 stop5h 12m
Air Canada
Deal found 25/7C$ 530

Find 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 July 2026.

Round-trip from

C$ 400

One-way from

C$ 251

Popular in

April

Cheapest in

August

Average price

C$ 603
Delta
  • Delta
  • 19/8-22/8
  • 2 total stops
  • 18h 50m total
  • Winnipeg to Portland
Search Deals
Air Canada
  • Air Canada
  • 8/9
  • 1 total stop
  • 5h 46m total
  • Winnipeg to Portland
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 119 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 21 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 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 July 2026.
Use the filters below to find and compare flights from Winnipeg to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 18/8

2:00 p.m.-9:32 a.m.

2 stops21h 32m

Portland

Tue 25/8

11:02 p.m.-11:52 a.m.

1 stop10h 50m

C$ 400

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 20/8

3:58 p.m.-11:20 p.m.

1 stop9h 22m

Portland

Mon 24/8

12:35 a.m.-11:54 a.m.

1 stop9h 19m

C$ 459

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 22/9

3:58 p.m.-8:16 p.m.

1 stop6h 18m

Portland

Fri 25/9

12:25 a.m.-11:51 a.m.

1 stop9h 26m

C$ 461

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 22/9

5:45 a.m.-9:31 a.m.

1 stop5h 46m

Portland

Sat 26/9

3:30 p.m.-11:55 p.m.

1 stop6h 25m

C$ 480

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 22/9

7:00 a.m.-9:05 p.m.

2 stops16h 05m

Portland

Sat 26/9

8:30 a.m.-10:33 p.m.

1 stop12h 03m

C$ 488

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 7/8

3:58 p.m.-11:20 p.m.

1 stop9h 22m

Portland

Mon 10/8

12:35 a.m.-11:54 a.m.

1 stop9h 19m

C$ 511
Quickest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 3/9

5:45 a.m.-9:31 a.m.

1 stop5h 46m

Portland

Sun 6/9

7:45 p.m.-2:57 a.m.

1 stop5h 12m

C$ 530
Cheapest one-way

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 10/9

8:45 a.m.-12:37 a.m.

2 stops17h 52m

C$ 283

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 8/9

2:00 p.m.-9:33 a.m.

2 stops21h 33m

C$ 290

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 10/9

10:10 a.m.-10:07 a.m.

3 stops25h 57m

C$ 340

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/7

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

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$ 430). Flying from Winnipeg to Portland in April is currently the most expensive (average of C$ 764). 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 Winnipeg to Portland?

Airfare is typical for this route at the moment.

Winnipeg to Portland flights typically cost between C$ 271 and C$ 867 in August.
The cheapest round-trip price found within the last 5 days was C$ 400 on Delta (19 Aug-22 Aug).

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 July 2026.
Get a feel of what it's like to fly with Air 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.
Air Canada
7.1
Good
11,392 reviews
Check prices

Crew

7.8

Comfort

7.1

Overall

7.1

Entertainment

6.8

Boarding

7.3

Food

6.3

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.
Air Canada
7.1
Good
11,392 reviews
Air Canada
7.1
Good
11,392 reviews
Check prices

Crew

7.8

Comfort

7.1

Overall

7.1

Entertainment

6.8

Boarding

7.3

Food

6.3

Reviews

1 / 20
6.0
Good

Paula,Mar 2026

YVR - PSP

Everything was OK, but we waited on the tarmac for an hour and 20 minutes after landing because there was no available gate. This is a daily occurrence at the Palm Springs airport, and happens with Air Canada and WestJet constantly.

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 46m. Fly via Delta, United Airlines, or Air Canada to get the fastest option. The distance between Winnipeg and Portland is about 1944 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What is the cheapest airline to fly from Winnipeg to Portland round-trip?

    According to our current data, Air Canada (C$ 351), offers the cheapest pricing from Winnipeg to Portland. You may be able to fly from Winnipeg to Portland for 42% less than the average price by searching for this airline.

  • 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$ 430). Flying from Winnipeg to Portland in April is currently the most expensive (average of C$ 764). 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
Tillamook
Salem
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 airline flying from Winnipeg to Portland

Discover the top airline 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 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 351AverageC$ 604FlexibilityNo 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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