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Cheap flights from Winnipeg to Portland from C$ 267

This is the cheapest round-trip 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
4 May — 11 May1
1 adult

Cheapflights Tip: The best prices from Winnipeg to Portland are usually found in August or July, booked 87 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 April 2025.

Round-trip from

C$ 267

Popular in

June

Cheapest in

August

Average price

C$ 452
WestJet
  • WestJet
  • 22/6-28/6
  • 2 total stops
  • 27h 48m total
  • Winnipeg to Portland
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 27 potential increase over avg. RT price).
Search Deals
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 April 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 April 2025.

Sun 22/66:30 p.m.YWG - PDX
1 stop20h 22mWestJet
Sat 28/61:45 p.m.PDX - YWG
1 stop7h 26mWestJet
Deal found 27/4C$ 267
Thu 12/65:20 a.m.YWG - PDX
1 stop6h 00mAir Canada
Thu 19/63:25 p.m.PDX - YWG
1 stop8h 07mAir Canada
Deal found 28/4C$ 328
Mon 12/55:35 p.m.YWG - PDX
2 stops8h 07mDelta
Thu 15/512:40 a.m.PDX - YWG
1 stop9h 17mDelta
Deal found 28/4C$ 334
Thu 12/68:30 a.m.YWG - PDX
1 stop6h 22mMultiple Airlines
Thu 19/61:19 p.m.PDX - YWG
2 stops20h 07mMultiple Airlines
Deal found 28/4C$ 461
Thu 18/124:30 p.m.YWG - PDX
1 stop8h 08mUnited Airlines
Thu 1/111:55 p.m.PDX - YWG
1 stop13h 29mUnited Airlines
Deal found 28/4C$ 491

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 April 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

Sun 22/6

6:30 p.m.-12:52 p.m.

1 stop20h 22m

Portland

Sat 28/6

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

1 stop7h 26m

C$ 267

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 12/6

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

1 stop6h 00m

Portland

Thu 19/6

3:25 p.m.-1:32 a.m.

1 stop8h 07m

C$ 328

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Mon 12/5

4:25 p.m.-10:53 p.m.

1 stop8h 28m

Portland

Fri 16/5

7:19 p.m.-1:09 p.m.

1 stop15h 50m

C$ 334

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 23/5

8:30 a.m.-1:05 p.m.

1 stop6h 35m

Portland

Sun 25/5

12:40 a.m.-11:57 a.m.

1 stop9h 17m

C$ 437

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 12/6

8:30 a.m.-12:52 p.m.

1 stop6h 22m

Portland

Thu 19/6

1:19 p.m.-11:26 a.m.

2 stops20h 07m

C$ 461

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

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 April 2025.

Booking 85 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$ 442). 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 April 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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland ranges from 18.0 - 142.0 mm per month. November is typically the wettest month, when rainfall can reach 142.0 mm. July is typically the driest time to visit Portland when rainfall is around 18.0 mm.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 21.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 5.0 C).

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 April 2025.
Delta
8.0
Very good
7,929 reviews
Check prices

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,929 reviews
Delta
8.0
Very good
7,929 reviews
Check prices

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,823 reviews
Delta
8.0
Very good
7,929 reviews
Check prices

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Canada
7.0
Good
9,228 reviews
Delta
8.0
Very good
7,929 reviews
Check prices

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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, WestJet (C$ 267), Air Canada (C$ 328), and Delta (C$ 334) offers the cheapest pricing from Winnipeg to Portland. You may be able to fly from Winnipeg to Portland for 40% 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$ 259). Flying from Winnipeg to Portland in December is currently the most expensive (average of C$ 442). 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 Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Seaside
Tillamook
Beaverton
Camas
Vancouver
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 April 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 243AverageC$ 354FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 263AverageC$ 411FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 333AverageC$ 404FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 337AverageC$ 444FlexibilityNo 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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