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Cheap flights from Winnipeg to Portland, ME from C$ 414

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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PWM
29 nov. — 6 dic.1
1 adult
1 adult, Economy, 0 bags

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 (PWM). 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 30 octubre 2025.

Round-trip from

C$ 568

One-way from

C$ 414
Air Canada
  • Air Canada
  • 8/4-9/4
  • 4 total stops
  • 23h 17m total
  • Winnipeg to Portland
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Delta
  • Delta
  • 12/12
  • 2 total stops
  • 26h 06m total
  • Winnipeg to Portland
Search Deals

Find flight deals from Winnipeg to Portland

Enter your travel dates to find the best prices.

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 30 octubre 2025.

mié. 8/45:30 a.m.YWG - PWM
2 stops14h 57mAir Canada
jue. 9/46:00 a.m.PWM - YWG
2 stops11h 27mAir Canada
Deal found 27/10C$ 568
mié. 8/42:15 p.m.YWG - PWM
1 stop6h 12mUnited Airlines
jue. 9/46:00 a.m.PWM - YWG
2 stops12h 17mUnited Airlines
Deal found 29/10C$ 752

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 30 octubre 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 - PWM

YWGPWM

Winnipeg

mié. 8/4

5:30 a.m.-9:27 p.m.

2 stops14h 57m

Portland

jue. 9/4

6:00 a.m.-4:27 p.m.

2 stops11h 27m

C$ 568

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

mié. 8/4

2:15 p.m.-9:27 p.m.

1 stop6h 12m

Portland

jue. 9/4

6:00 a.m.-5:17 p.m.

2 stops12h 17m

C$ 752

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

vie. 12/12

2:20 p.m.-9:17 p.m.

1 stop5h 57m

C$ 525

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

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, Maine?

Currently, May is the cheapest month in which you can book a flight from Winnipeg to Portland, Maine (average of C$ 228). Flying from Winnipeg to Portland, Maine in December is currently the most expensive (average of C$ 499). 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 PWM?

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 30 octubre 2025.

When flying from Winnipeg to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 50% versus a flight at noon.

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, Maine?

    Airlines like Air Canada and United Airlines fly from Winnipeg to Portland, Maine in about 6h 12m. The time it takes to get you to your destination can typically vary by up to 8h 45m. The distance between Winnipeg and Portland, Maine is about 2150 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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, Maine?

    Currently, May is the cheapest month in which you can book a flight from Winnipeg to Portland, Maine (average of C$ 228). Flying from Winnipeg to Portland, Maine in December is currently the most expensive (average of C$ 499). 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
North Conway

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Alternative routes for Winnipeg to Portland

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Winnipeg to Boston 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?

Cheapflights helps you search for flights from Winnipeg to Portland via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Winnipeg to Portland.

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

Need flexible booking options for your flight to Portland from Winnipeg? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Portland from Winnipeg today and book when prices fit your budget.

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