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Cheap flights from Winnipeg to Portland from C$ 196

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 22/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
24 May — 31 May1
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 24 April 2026.

Sat 23/57:00 a.m.
YWG
-
PDX
2 stops8h 50m
WestJet
Sat 30/52:30 p.m.
PDX
-
YWG
1 stop5h 40m
WestJet
Deal found 20/4C$ 357
Tue 19/510:10 a.m.
YWG
-
PDX
1 stop5h 40m
WestJet
Tue 26/52:30 p.m.
PDX
-
YWG
2 stops19h 30m
WestJet
Deal found 19/4C$ 380
Tue 7/75:40 a.m.
YWG
-
PDX
1 stop5h 51m
Air Canada
Wed 5/87:45 p.m.
PDX
-
YWG
1 stop15h 25m
Air Canada
Deal found 19/4C$ 453
Wed 20/55:40 a.m.
YWG
-
PDX
1 stop5h 50m
Air Canada
Sun 24/53:30 p.m.
PDX
-
YWG
2 stops18h 50m
Air Canada
Deal found 19/4C$ 469
Wed 15/73:59 p.m.
YWG
-
PDX
1 stop9h 21m
Delta
Sat 18/712:35 a.m.
PDX
-
YWG
1 stop9h 19m
Delta
Deal found 22/4C$ 494
Wed 20/54:15 p.m.
YWG
-
PDX
2 stops23h 35m
WestJet
Sun 24/52:30 p.m.
PDX
-
YWG
2 stops22h 10m
WestJet
Deal found 19/4C$ 495

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 24 April 2026.

Round-trip from

C$ 357

One-way from

C$ 196

Popular in

March

Cheapest in

August

Average price

C$ 635
WestJet
  • WestJet
  • 23/5-30/5
  • 3 total stops
  • 14h 30m total
  • Winnipeg to Portland
Search Deals
WestJet
  • WestJet
  • 22/6
  • 1 total stop
  • 5h 40m total
  • Winnipeg to Portland
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 216 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 24 April 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 19/5

10:10 a.m.-1:50 p.m.

1 stop5h 40m

Portland

Tue 26/5

2:30 p.m.-12:00 p.m.

2 stops19h 30m

C$ 380

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 7/7

5:40 a.m.-9:31 a.m.

1 stop5h 51m

Portland

Wed 5/8

7:45 p.m.-1:10 p.m.

1 stop15h 25m

C$ 453
Quickest round-trip

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 15/7

3:59 p.m.-11:20 p.m.

1 stop9h 21m

Portland

Sat 18/7

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

1 stop9h 19m

C$ 494

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 20/5

4:15 p.m.-1:50 p.m.

2 stops23h 35m

Portland

Sun 24/5

2:30 p.m.-2:40 p.m.

2 stops22h 10m

C$ 495

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 4/5

5:40 a.m.-9:30 a.m.

1 stop5h 50m

Portland

Thu 7/5

7:45 p.m.-1:04 p.m.

1 stop15h 19m

C$ 538

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 7/6

12:46 p.m.-8:17 p.m.

1 stop9h 31m

Portland

Sun 14/6

11:51 a.m.-11:29 p.m.

1 stop9h 38m

C$ 547
Cheapest one-way
Quickest one-way

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 24/6

10:10 a.m.-1:50 p.m.

1 stop5h 40m

C$ 197

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 20/6

5:40 a.m.-9:31 a.m.

1 stop5h 51m

C$ 231

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 6/6

7:00 a.m.-1:50 p.m.

2 stops8h 50m

C$ 235

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 6/6

5:40 a.m.-9:30 a.m.

1 stop5h 50m

C$ 238

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/4

Showing 1-10 of 12 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$ 306). Flying from Winnipeg to Portland in March is currently the most expensive (average of C$ 782). 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?

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 24 April 2026.
Get a feel of what it's like to fly with WestJet and 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.
WestJet
7.2
Good
3,325 reviews
Check prices

Boarding

7.4

Comfort

7.0

Overall

7.2

Crew

7.9

Entertainment

6.1

Food

6.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
WestJet
7.2
Good
3,325 reviews
WestJet
7.2
Good
3,325 reviews
Check prices

Boarding

7.4

Comfort

7.0

Overall

7.2

Crew

7.9

Entertainment

6.1

Food

6.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
Air Canada
7.1
Good
10,961 reviews
WestJet
7.2
Good
3,325 reviews
Check prices

Boarding

7.4

Comfort

7.0

Overall

7.2

Crew

7.9

Entertainment

6.1

Food

6.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.

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 40m. Fly via WestJet, Air Canada, or Delta 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 are the cheapest airlines flying from Winnipeg to Portland round-trip?

    According to our current data, WestJet (C$ 222), and Air Canada (C$ 290) offers the cheapest pricing from Winnipeg to Portland. You may be able to fly from Winnipeg to Portland for 59% 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$ 306). Flying from Winnipeg to Portland in March is currently the most expensive (average of C$ 782). 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
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 2 airlines flying from Winnipeg to Portland

Discover the top 2 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 24 April 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 222AverageC$ 501FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 290AverageC$ 539FlexibilityNo 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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