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Cheap flights from Winnipeg to Portland from C$ 259

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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
11 Jan — 18 Jan1
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 12 December 2025.

Thu 18/1210:45 a.m.YWG - PDX
1 stop9h 45mAir Canada
Thu 1/13:15 p.m.PDX - YWG
1 stop7h 59mAir Canada
Deal found 10/12C$ 655
Fri 19/125:45 p.m.YWG - PDX
1 stop21h 15mWestJet
Sun 21/129:19 a.m.PDX - YWG
2 stops26h 33mWestJet
Deal found 9/12C$ 750
Thu 18/125:55 a.m.YWG - PDX
2 stops14h 55mWestJet
Thu 1/112:29 p.m.PDX - YWG
2 stops10h 12mWestJet
Deal found 11/12C$ 760
Thu 18/126:00 a.m.YWG - PDX
3 stops17h 59mAmerican Airlines
Thu 1/110:21 p.m.PDX - YWG
2 stops23h 14mAmerican Airlines
Deal found 10/12C$ 1,703
Sat 27/125:55 a.m.YWG - PDX
2 stops12h 32mMultiple Airlines
Sat 27/128:23 p.m.PDX - YWG
1 stop27h 00mMultiple Airlines
Deal found 11/12C$ 2,142
Sat 27/1210:45 a.m.YWG - PDX
1 stop5h 55mAir Canada
Sat 27/127:00 p.m.PDX - YWG
1 stop21h 09mAir Canada
Deal found 11/12C$ 2,169
Fri 19/125:40 p.m.YWG - PDX
2 stops26h 28mMultiple Airlines
Sun 21/126:50 p.m.PDX - YWG
3 stops23h 16mMultiple Airlines
Deal found 9/12C$ 2,342

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 12 December 2025.

Round-trip from

C$ 439

One-way from

C$ 259

Popular in

June

Cheapest in

August

Average price

C$ 484
24/1-31/1
  • 24/1-31/1
  • 3 total stops
  • 14h 11m total
  • Winnipeg to Portland
Search Deals
7/1
  • 7/1
  • 3 total stops
  • 40h 39m total
  • Winnipeg to Portland
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 12 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).
Search Deals
Average for round-trip flights in December 2025
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 12 December 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

Sat 24/1

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

1 stop5h 55m

Portland

Sat 31/1

9:50 a.m.-8:06 p.m.

2 stops8h 16m

C$ 439

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 24/1

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

1 stop5h 55m

Portland

Sat 31/1

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

1 stop6h 19m

C$ 444

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 16/1

5:05 p.m.-1:48 p.m.

1 stop22h 43m

Portland

Sun 18/1

8:18 a.m.-12:43 a.m.

1 stop14h 25m

C$ 450

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 1/3

11:53 a.m.-8:30 p.m.

1 stop10h 37m

Portland

Tue 3/3

12:40 a.m.-11:01 a.m.

1 stop8h 21m

C$ 485

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 9/2

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

1 stop14h 30m

Portland

Mon 16/2

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

1 stop7h 59m

C$ 492

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 6/2

10:40 a.m.-6:30 p.m.

1 stop9h 50m

Portland

Mon 9/2

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

1 stop7h 59m

C$ 492

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 1/3

8:00 a.m.-6:30 p.m.

2 stops12h 30m

Portland

Wed 4/3

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

1 stop6h 19m

C$ 531

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 16/1

2:20 p.m.-12:31 a.m.

2 stops12h 11m

Portland

Sun 18/1

3:45 p.m.-11:57 a.m.

2 stops18h 12m

C$ 536

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 7/1

6:55 p.m.-9:34 a.m.

3 stops40h 39m

C$ 259

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 24/1

12:55 p.m.-11:18 a.m.

3 stops48h 23m

C$ 265

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 17 results
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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$ 193). Flying from Winnipeg to Portland in June is currently the most expensive (average of C$ 480). 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 12 December 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 12 December 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
9,095 reviews
Check prices

Entertainment

7.1

Crew

8.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2025

AMS - EWR

It was good! The first 3/4 of the trip was uncomfortably cold. Only one option for lunch that I didn’t enjoy (vegetarian).
United Airlines
7.4
Good
9,095 reviews
United Airlines
7.4
Good
9,095 reviews
Check prices

Entertainment

7.1

Crew

8.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2025

AMS - EWR

It was good! The first 3/4 of the trip was uncomfortably cold. Only one option for lunch that I didn’t enjoy (vegetarian).
WestJet
7.2
Good
3,195 reviews
United Airlines
7.4
Good
9,095 reviews
Check prices

Entertainment

7.1

Crew

8.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2025

AMS - EWR

It was good! The first 3/4 of the trip was uncomfortably cold. Only one option for lunch that I didn’t enjoy (vegetarian).
Air Canada
7.1
Good
10,516 reviews
United Airlines
7.4
Good
9,095 reviews
Check prices

Entertainment

7.1

Crew

8.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2025

AMS - EWR

It was good! The first 3/4 of the trip was uncomfortably cold. Only one option for lunch that I didn’t enjoy (vegetarian).

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 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, United Airlines (C$ 168), WestJet (C$ 228), and Air Canada (C$ 311) offers the cheapest pricing from Winnipeg to Portland. You may be able to fly from Winnipeg to Portland for 65% 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$ 193). Flying from Winnipeg to Portland in June is currently the most expensive (average of C$ 480). 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 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 12 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 228AverageC$ 443FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 306AverageC$ 420FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 322AverageC$ 442FlexibilityNo 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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