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Cheap flights from Winnipeg to Portland from C$ 188

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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
3 Aug — 10 Aug1
1 adult

Cheapflights Tip: The best prices from Winnipeg to Portland are usually found in August or July, booked 57 days in advance, depart on a Sunday or Friday and return on a Monday

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 29 July 2025.

Round-trip from

C$ 335

One-way from

C$ 188

Popular in

June

Cheapest in

August

Average price

C$ 369
Air Canada
  • Air Canada
  • 21/8-25/8
  • 2 total stops
  • 12h 40m total
  • Winnipeg to Portland
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Air Canada
  • Air Canada
  • 1/9
  • 1 total stop
  • 6h 10m total
  • Winnipeg to Portland
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 46 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 20 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Winnipeg to Portland

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 29 July 2025.

Thu 21/85:20 a.m.YWG - PDX
1 stop6h 10mAir Canada
Mon 25/86:15 a.m.PDX - YWG
1 stop6h 30mAir Canada
Deal found 28/7C$ 335
Thu 21/82:20 p.m.YWG - PDX
1 stop10h 05mUnited Airlines
Mon 25/81:45 p.m.PDX - YWG
2 stops21h 24mUnited Airlines
Deal found 28/7C$ 416
Fri 12/99:05 p.m.YWG - PDX
1 stop18h 00mWestJet
Fri 19/91:45 p.m.PDX - YWG
1 stop5h 45mWestJet
Deal found 29/7C$ 431
Fri 29/88:30 a.m.YWG - PDX
1 stop6h 34mDelta
Mon 1/91:45 p.m.PDX - YWG
1 stop7h 25mDelta
Deal found 29/7C$ 442
Fri 12/96:30 a.m.YWG - PDX
2 stops10h 14mMultiple Airlines
Fri 19/91:45 p.m.PDX - YWG
1 stop5h 45mMultiple Airlines
Deal found 29/7C$ 453

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 29 July 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 21/8

5:20 a.m.-9:30 a.m.

1 stop6h 10m

Portland

Mon 25/8

6:15 a.m.-2:45 p.m.

1 stop6h 30m

C$ 335

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 21/8

2:20 p.m.-10:25 p.m.

1 stop10h 05m

Portland

Mon 25/8

1:45 p.m.-1:09 p.m.

2 stops21h 24m

C$ 416

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 12/9

9:05 p.m.-1:05 p.m.

1 stop18h 00m

Portland

Fri 19/9

1:45 p.m.-9:30 p.m.

1 stop5h 45m

C$ 431

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 29/8

8:30 a.m.-1:04 p.m.

1 stop6h 34m

Portland

Mon 1/9

1:45 p.m.-11:10 p.m.

1 stop7h 25m

C$ 442

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 12/9

6:30 a.m.-2:44 p.m.

2 stops10h 14m

Portland

Fri 19/9

1:45 p.m.-9:30 p.m.

1 stop5h 45m

C$ 453

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 1/9

5:20 a.m.-9:30 a.m.

1 stop6h 10m

C$ 188

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 10/9

4:25 p.m.-12:45 a.m.

2 stops10h 20m

C$ 206

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 1/9

6:15 p.m.-12:48 p.m.

2 stops20h 33m

C$ 232

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 15/8

9:00 a.m.-6:57 p.m.

3 stops35h 57m

C$ 416

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/7

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 25 July 2025.

Booking 56 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$ 259). Flying from Winnipeg to Portland in December is currently the most expensive (average of C$ 418). 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 29 July 2025.

It’s typically best to fly out from Winnipeg to Portland in the afternoon. Doing so could potentially save you 30% on the flight price compared to flying in the morning, which is usually more expensive.

What’s the top layover airport for flights from Winnipeg to Portland?

Share of one-stop round-trip flights from Winnipeg to Portland chosen by Cheapflights users in the past 12 months, using the same layover each way.

Calgary (YYC) – chosen by Cheapflights users on 43% of one-stop itineraries from Winnipeg to Portland on Cheapflights.

What’s the cheapest layover airport for flights from Winnipeg to Portland?

Average round-trip fare for 1-stop flights from Winnipeg to Portland, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 329.

What’s the fastest layover option from Winnipeg to Portland?

Shortest average travel time for 1-stop one-way flights from Winnipeg to Portland, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Vancouver (YVR) have the shortest average one-way travel time for 1-stop routes: 3h 07m.

Which airport typically offers the quickest layover for flights from Winnipeg to Portland?

Average layover duration for 1-stop one-way flights from Winnipeg to Portland, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 1h 08m.

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 29 July 2025.
Get a feel of what it's like to fly with Delta,United Airlines, andWestJet 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.
Delta
8.0
Very good
7,977 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,977 reviews
Delta
8.0
Very good
7,977 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,899 reviews
Delta
8.0
Very good
7,977 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
WestJet
7.2
Good
2,973 reviews
Delta
8.0
Very good
7,977 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air Canada
7.1
Good
9,822 reviews
Delta
8.0
Very good
7,977 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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.

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

    According to our current data, Air Canada (C$ 335), United Airlines (C$ 416), and WestJet (C$ 431) offers the cheapest pricing from Winnipeg to Portland. You may be able to fly from Winnipeg to Portland for 25% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Winnipeg to Portland one-way?

    To fly one-way, consider booking your trip with Air Canada, which is currently one of the cheapest options available, starting at C$ 188. United Airlines flights start at C$ 206 while deals on WestJet start at C$ 232 one-way.

  • 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$ 259). Flying from Winnipeg to Portland in December is currently the most expensive (average of C$ 418). 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

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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 4 airlines flying from Winnipeg to Portland

Discover the top 4 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 29 July 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 235AverageC$ 368FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 261AverageC$ 406FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 290AverageC$ 436FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 341AverageC$ 399FlexibilityNo cancel feeOn-timeN/A
Search Delta 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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