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

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 345.

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

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

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

Vancouver (YVR) – chosen by Cheapflights users on 45% of one-stop itineraries from Winnipeg to Portland on Cheapflights.

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

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 6h 18m.

How long is the flight from Winnipeg to Portland?

There are many flights that can get you from Winnipeg to Portland in 8h 20m. Fly via United Airlines, Delta, or Air Canada 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$ 229), Air Canada (C$ 293), and United Airlines (C$ 307) offers the cheapest pricing from Winnipeg to Portland. You may be able to fly from Winnipeg to Portland for 49% less than the average price by searching for these airlines.

What is the cheapest day to fly from Winnipeg to Portland?

Travelers seeking maximum savings on their Winnipeg to Portland flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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.

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).

What are the most popular airlines that fly from Winnipeg to Portland?

The most popular airlines flying from Winnipeg to Portland are Air Canada, United Airlines and WestJet. Something to consider prior to booking your flight.

What is the cheapest day to fly round-trip from Winnipeg to Portland?

Flying to your destination on a Sunday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Portland. Check prices with Cheapflights to find a great deal for your trip.

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

Users have found that booking a flight from Winnipeg to Portland at least 57 days early can save you up to 146% on average compared to booking a flight this week. If booking 57 days before your flight isn’t an option for you, users have found flights from Winnipeg to Portland for as little as C$ 285 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 1,093 for flights departing within the next 3 days.

What is the cheapest month to fly from Winnipeg to Portland?

August can be a great time to fly to Portland from Winnipeg with a flight ticket averaging about C$ 449. Cheapflights users have found deals in the month of August for as cheap as C$ 226. The most expensive prices can be found in the month of June.

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.

C$ 198+ Cheap Flights from Winnipeg to Portland

Q: How much does it cost to fly round-trip from Winnipeg to Portland?

Airfare is typical for this route at the moment. Winnipeg to Portland flights typically cost between C$ 269 and C$ 502 in October. The cheapest round-trip price found within the last 3 days was C$ 335 on United Airlines (17 Oct-20 Oct).

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

Round-trip from	C$ 335
One-way from	C$ 198
Popular in	June
Cheapest in	August
Average price	C$ 385

United Airlines
17/10-20/10
4 total stops
27h 39m total
Winnipeg to Portland

Search Deals

Air Canada
25/10
1 total stop
6h 00m total
Winnipeg to Portland

Search Deals

Highest demand for flights based on searches. 7% potential increase in price (C$ 49 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).

Search Deals

Average for round-trip flights in September 2025

Search Deals

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 11 September 2025.

Fri 17/104:25 p.m.YWG - PDX

1 stop8h 20mUnited Airlines

Mon 20/103:50 p.m.PDX - YWG

3 stops19h 19mUnited Airlines

Deal found 11/9C$ 335

Tue 7/107:10 p.m.YWG - PDX

1 stop5h 51mAir Canada

Tue 14/103:25 p.m.PDX - YWG

1 stop8h 37mAir Canada

Deal found 10/9C$ 371

Fri 26/99:00 a.m.YWG - PDX

1 stop11h 58mDelta

Sun 28/912:45 a.m.PDX - YWG

1 stop9h 09mDelta

Deal found 9/9C$ 407

Thu 25/126:00 a.m.YWG - PDX

1 stop14h 30mAir Canada

Sun 4/13:15 p.m.PDX - YWG

1 stop7h 54mAir Canada

Deal found 9/9C$ 435

Sun 5/108:30 a.m.YWG - PDX

1 stop6h 35mWestJet

Thu 9/101:45 p.m.PDX - YWG

1 stop5h 45mWestJet

Deal found 10/9C$ 450

Tue 7/1012:20 p.m.YWG - PDX

1 stop10h 06mDelta

Mon 13/1012:40 a.m.PDX - YWG

1 stop8h 50mDelta

Deal found 10/9C$ 488

Thu 18/122:20 p.m.YWG - PDX

1 stop10h 20mUnited Airlines

Thu 1/111:55 p.m.PDX - YWG

1 stop10h 02mUnited Airlines

Deal found 11/9C$ 516

Fri 26/96:30 a.m.YWG - PDX

2 stops15h 55mMultiple Airlines

Mon 29/91:45 p.m.PDX - YWG

1 stop17h 16mMultiple Airlines

Deal found 9/9C$ 525

Best flights from Winnipeg to Portland
Discover carefully curated flight deals from Winnipeg to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 11 September 2025.

Fri 17/104:25 p.m.YWG - PDX

1 stop8h 20mUnited Airlines

Mon 20/1011:59 p.m.PDX - YWG

1 stop13h 32mUnited Airlines

Deal found 11/9C$ 335

Fri 26/99:00 a.m.YWG - PDX

1 stop11h 58mDelta

Sun 28/912:45 a.m.PDX - YWG

1 stop9h 09mDelta

Deal found 9/9C$ 407

Tue 7/105:05 a.m.YWG - PDX

2 stops11h 37mAir Canada

Tue 14/101:44 p.m.PDX - YWG

2 stops10h 18mAir Canada

Deal found 10/9C$ 410

Sun 5/108:30 a.m.YWG - PDX

1 stop6h 35mWestJet

Thu 9/101:45 p.m.PDX - YWG

2 stops7h 55mWestJet

Deal found 10/9C$ 450

Fri 26/96:30 a.m.YWG - PDX

2 stops15h 55mMultiple Airlines

Mon 29/91:45 p.m.PDX - YWG

1 stop17h 16mMultiple Airlines

Deal found 9/9C$ 525

Wed 4/310:45 a.m.YWG - PDX

1 stop6h 00mAir Canada

Thu 5/39:50 a.m.PDX - YWG

1 stop6h 19mAir Canada

Deal found 9/9C$ 427

Thu 25/126:00 a.m.YWG - PDX

1 stop14h 30mAir Canada

Sun 4/13:15 p.m.PDX - YWG

1 stop7h 54mAir Canada

Deal found 9/9C$ 435

Thu 18/1210:45 a.m.YWG - PDX

1 stop6h 00mAir Canada

Thu 1/19:50 a.m.PDX - YWG

1 stop6h 19mAir Canada

Deal found 10/9C$ 536

Last-minute flights from Winnipeg to Portland
Discover last-minute flight deals from Winnipeg to Portland. Data last updated 11 September 2025 and is based on user searches.

Fri 26/99:00 a.m.YWG - PDX

1 stop11h 58mDelta

Sun 28/912:45 a.m.PDX - YWG

1 stop9h 09mDelta

Deal found 9/9C$ 407

Fri 26/96:30 a.m.YWG - PDX

2 stops15h 55mMultiple Airlines

Mon 29/91:45 p.m.PDX - YWG

1 stop17h 16mMultiple Airlines

Deal found 9/9C$ 525

Sat 27/98:30 a.m.YWG - PDX

1 stop6h 34mDelta

Sun 28/912:45 a.m.PDX - YWG

1 stop9h 09mDelta

Deal found 11/9C$ 557

Sun 5/108:30 a.m.YWG - PDX

1 stop6h 35mWestJet

Thu 9/101:45 p.m.PDX - YWG

1 stop5h 45mWestJet

Deal found 10/9C$ 450

Tue 7/107:10 p.m.YWG - PDX

1 stop5h 51mAir Canada

Tue 14/103:25 p.m.PDX - YWG

1 stop8h 37mAir Canada

Deal found 10/9C$ 371

Tue 7/1012:20 p.m.YWG - PDX

1 stop10h 06mDelta

Mon 13/1012:40 a.m.PDX - YWG

1 stop8h 50mDelta

Deal found 10/9C$ 488

Fri 17/104:25 p.m.YWG - PDX

1 stop8h 20mUnited Airlines

Mon 20/1011:59 p.m.PDX - YWG

1 stop13h 32mUnited Airlines

Deal found 11/9C$ 335

One-way flights from Winnipeg to Portland
Search for one-way flight options from Winnipeg to Portland. Find affordable one-way fares based on user searches. Data last updated 11 September 2025.

Sat 25/105:20 a.m.YWG - PDX

1 stop6h 00mAir Canada

Deal found 10/9C$ 198

Sat 25/1012:15 p.m.YWG - PDX

3 stops22h 08mMultiple Airlines

Deal found 10/9C$ 202

Sun 26/1012:55 p.m.YWG - PDX

2 stops22h 44mMultiple Airlines

Deal found 11/9C$ 269

Fly from

Fly to

Route

Depart

Return

Price

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 17/10

4:25 p.m.-10:45 p.m.

1 stop8h 20m

Portland

Mon 20/10

11:59 p.m.-3:31 p.m.

1 stop13h 32m

C$ 335

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 26/9

9:00 a.m.-6:58 p.m.

1 stop11h 58m

Portland

Sun 28/9

12:45 a.m.-11:54 a.m.

1 stop9h 09m

C$ 407

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Tue 7/10

5:05 a.m.-2:42 p.m.

2 stops11h 37m

Portland

Tue 14/10

1:44 p.m.-2:02 a.m.

2 stops10h 18m

C$ 410

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Wed 4/3

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

1 stop6h 00m

Portland

Thu 5/3

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

1 stop6h 19m

C$ 427

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 25/12

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

1 stop14h 30m

Portland

Sun 4/1

3:15 p.m.-1:09 a.m.

1 stop7h 54m

C$ 435

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sun 5/10

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

1 stop6h 35m

Portland

Thu 9/10

1:45 p.m.-11:40 p.m.

2 stops7h 55m

C$ 450

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Fri 26/9

6:30 a.m.-8:25 p.m.

2 stops15h 55m

Portland

Mon 29/9

1:45 p.m.-9:01 a.m.

1 stop17h 16m

C$ 525

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Thu 18/12

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

1 stop6h 00m

Portland

Thu 1/1

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

1 stop6h 19m

C$ 536

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 25/10

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

1 stop6h 00m

C$ 198

WinnipegPortland

YWG - PDX

YWGPDX

Winnipeg

Sat 25/10

12:15 p.m.-8:23 a.m.

3 stops22h 08m

C$ 202

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

Showing 1-10 of 11 results

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

Prices

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

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$ 404). 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?

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.

How much does it cost to fly round-trip from Winnipeg to Portland?

Reviews of airlines servicing Portland

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

8,937 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.

United Airlines

7.4

Good

8,937 reviews

United Airlines

7.4

Good

8,937 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.

WestJet

7.2

Good

3,091 reviews

United Airlines

7.4

Good

8,937 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.

Air Canada

7.1

Good

10,000 reviews

United Airlines

7.4

Good

8,937 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.

Related info for your journey

How long is the flight from Winnipeg to Portland?
There are many flights that can get you from Winnipeg to Portland in 8h 20m. Fly via United Airlines, Delta, or Air Canada 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$ 229), Air Canada (C$ 293), and United Airlines (C$ 307) offers the cheapest pricing from Winnipeg to Portland. You may be able to fly from Winnipeg to Portland for 49% 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$ 404). 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

Vancouver

Seaside

Tillamook

Cannon Beach

Lincoln City

Browse thousands of different options on Cheapflights for your next trip

Top 3 airlines flying from Winnipeg to Portland

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 229	AverageC$ 441	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
Air Canada	CheapestC$ 293	AverageC$ 443	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
United Airlines	CheapestC$ 307	AverageC$ 410	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights

Fly with Cheapflights

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!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

Cheap flights from Winnipeg to Portland from C$ 198

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 25/10. Fares are subject to change and may not be available on all flights or dates of travel.

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

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Winnipeg to Portland

Cheapest flights from Winnipeg to PortlandExplore 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 11 September 2025.

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 11 September 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Winnipeg to Portland that are best for you.

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.

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?

What is the cheapest month to book a flight from Winnipeg to Portland?

What is the cheapest time of day to fly from YWG to PDX?

How much does it cost to fly round-trip from Winnipeg to Portland?

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

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

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

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

Reviews of airlines servicing Portland

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.

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?

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

Can I find deals for flights from Winnipeg to Portland that include hotel bookings?

How can I find direct flights from Winnipeg to Portland?

Can I find deals for business class flights from Winnipeg to Portland?

What is the cheapest month to book a flight from Winnipeg to Portland?

Travelling to a place near Portland?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Portland

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Winnipeg to Portland

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?

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Portland?

Can Cheapflights find flights from Winnipeg to Portland with no change fees?

Can Cheapflights notify me if prices for flights from Winnipeg to Portland become cheaper?

100% Free

Book with Flexibility

Travel Smart

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 11 September 2025.