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Cheap flights from Winnipeg to Portland from C$ 241

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 23/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
26 Feb — 5 Mar1
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 January 2026.

Fri 1/57:00 a.m.
YWG
-
PDX
2 stops8h 43m
Multiple Airlines
Wed 6/52:30 p.m.
PDX
-
YWG
1 stop5h 40m
Multiple Airlines
Deal found 27/1C$ 472
Sat 28/22:20 p.m.
YWG
-
PDX
1 stop10h 36m
United Airlines
Wed 4/311:59 p.m.
PDX
-
YWG
1 stop9h 58m
United Airlines
Deal found 25/1C$ 475
Fri 1/52:00 p.m.
YWG
-
PDX
2 stops24h 34m
United Airlines
Wed 6/51:37 p.m.
PDX
-
YWG
2 stops20h 15m
United Airlines
Deal found 27/1C$ 485
Sat 28/22:20 p.m.
YWG
-
PDX
1 stop10h 36m
United Airlines
Fri 6/311:59 p.m.
PDX
-
YWG
1 stop9h 58m
United Airlines
Deal found 26/1C$ 487
Sat 28/22:20 p.m.
YWG
-
PDX
1 stop10h 36m
Lufthansa
Fri 6/35:05 a.m.
PDX
-
YWG
2 stops28h 52m
Lufthansa
Deal found 26/1C$ 511
Tue 28/49:05 p.m.
YWG
-
PDX
1 stop18h 45m
WestJet
Sun 3/52:30 p.m.
PDX
-
YWG
1 stop18h 40m
WestJet
Deal found 27/1C$ 527
Thu 26/310:10 p.m.
YWG
-
PDX
1 stop13h 05m
Air Canada
Sun 29/33:15 p.m.
PDX
-
YWG
1 stop7h 59m
Air Canada
Deal found 26/1C$ 534
Tue 28/46:00 a.m.
YWG
-
PDX
2 stops12h 22m
Multiple Airlines
Sun 3/52:30 p.m.
PDX
-
YWG
1 stop22h 55m
Multiple Airlines
Deal found 27/1C$ 535

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 January 2026.

Round-trip from

C$ 472

One-way from

C$ 241

Popular in

January

Cheapest in

August

Average price

C$ 863
WestJet
  • WestJet
  • 1/5-6/5
  • 3 total stops
  • 14h 23m total
  • Winnipeg to Portland
Search Deals
23/2
  • 23/2
  • 1 total stop
  • 14h 45m total
  • Winnipeg to Portland
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 111 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 2026.
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

Fri 1/5

7:00 a.m.-1:43 p.m.

2 stops8h 43m

Portland

Wed 6/5

2:30 p.m.-10:10 p.m.

1 stop5h 40m

C$ 472

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 28/2

2:20 p.m.-10:56 p.m.

1 stop10h 36m

Portland

Wed 4/3

11:59 p.m.-11:57 a.m.

1 stop9h 58m

C$ 475

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 1/5

2:00 p.m.-12:34 p.m.

2 stops24h 34m

Portland

Wed 6/5

1:37 p.m.-11:52 a.m.

2 stops20h 15m

C$ 485

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 28/2

2:20 p.m.-10:56 p.m.

1 stop10h 36m

Portland

Fri 6/3

11:59 p.m.-11:57 a.m.

1 stop9h 58m

C$ 487

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 28/2

2:20 p.m.-9:42 a.m.

2 stops21h 22m

Portland

Fri 6/3

1:39 p.m.-11:57 a.m.

2 stops20h 18m

C$ 511

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 26/3

10:10 p.m.-9:15 a.m.

1 stop13h 05m

Portland

Sun 29/3

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

1 stop7h 59m

C$ 549

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 23/2

8:30 p.m.-9:15 a.m.

1 stop14h 45m

C$ 241

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 23/2

6:00 a.m.-6:30 p.m.

1 stop14h 30m

C$ 308

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/1

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

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

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Portland. Price data was last updated on 23 January 2026.

Booking 36 days in advance of your planned departure date is, on average, the best time to get cheap flights from Winnipeg to Portland. 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 Winnipeg to Portland?

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Portland (average of C$ 192). Flying from Winnipeg to Portland in January is currently the most expensive (average of C$ 483). 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 27 January 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
3,251 reviews
Check prices

Food

6.2

Boarding

7.4

Overall

7.2

Comfort

7.0

Crew

7.9

Entertainment

6.1

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying
WestJet
7.2
Good
3,251 reviews
WestJet
7.2
Good
3,251 reviews
Check prices

Food

6.2

Boarding

7.4

Overall

7.2

Comfort

7.0

Crew

7.9

Entertainment

6.1

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying
Air Canada
7.1
Good
10,660 reviews
WestJet
7.2
Good
3,251 reviews
Check prices

Food

6.2

Boarding

7.4

Overall

7.2

Comfort

7.0

Crew

7.9

Entertainment

6.1

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying

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 10h 36m. Fly via United Airlines 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$ 226), and Air Canada (C$ 309) offers the cheapest pricing from Winnipeg to Portland. You may be able to fly from Winnipeg to Portland for 55% 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$ 192). Flying from Winnipeg to Portland in January is currently the most expensive (average of C$ 483). 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 27 January 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 226AverageC$ 434FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 309AverageC$ 435FlexibilityNo 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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