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Cheap flights from Winnipeg to Portland, ME from C$ 463

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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PWM
14 Jul — 21 Jul1
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 14 June 2026.

Tue 22/92:00 p.m.
YWG
-
PWM
1 stop6h 23m
United Airlines
Sat 26/97:57 a.m.
PWM
-
YWG
2 stops15h 36m
United Airlines
Deal found 12/6C$ 762
Sat 5/122:15 p.m.
YWG
-
PWM
1 stop6h 12m
United Airlines
Wed 9/123:15 p.m.
PWM
-
YWG
2 stops21h 24m
United Airlines
Deal found 11/6C$ 764
Sat 5/126:35 a.m.
YWG
-
PWM
2 stops14h 48m
Delta
Wed 9/123:00 p.m.
PWM
-
YWG
2 stops9h 34m
Delta
Deal found 9/6C$ 765
Thu 20/87:00 a.m.
YWG
-
PWM
1 stop6h 34m
United Airlines
Tue 1/95:03 p.m.
PWM
-
YWG
1 stop6h 30m
United Airlines
Deal found 10/6C$ 800
Thu 18/67:00 a.m.
YWG
-
PWM
1 stop13h 51m
United Airlines
Thu 25/66:00 a.m.
PWM
-
YWG
1 stop17h 38m
United Airlines
Deal found 13/6C$ 1,231
Thu 18/67:00 a.m.
YWG
-
PWM
2 stops27h 55m
WestJet
Thu 25/611:48 a.m.
PWM
-
YWG
2 stops10h 52m
WestJet
Deal found 13/6C$ 1,299

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 (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 14 June 2026.

Round-trip from

C$ 762

One-way from

C$ 463
United Airlines
  • United Airlines
  • 22/9-26/9
  • 3 total stops
  • 21h 59m total
  • Winnipeg to Portland
Search Deals
WestJet
  • WestJet
  • 3/7
  • 2 total stops
  • 29h 41m total
  • Winnipeg to Portland
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 14 June 2026.
Use the filters below to find and compare flights from Winnipeg to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Tue 22/9

2:00 p.m.-9:23 p.m.

1 stop6h 23m

Portland

Sat 26/9

7:57 a.m.-10:33 p.m.

2 stops15h 36m

C$ 762

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Sat 5/12

6:35 a.m.-10:23 p.m.

2 stops14h 48m

Portland

Wed 9/12

3:00 p.m.-11:34 p.m.

2 stops9h 34m

C$ 764

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Sat 5/12

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

1 stop6h 12m

Portland

Wed 9/12

3:15 p.m.-11:39 a.m.

2 stops21h 24m

C$ 764
Quickest round-trip

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Thu 20/8

7:00 a.m.-2:34 p.m.

1 stop6h 34m

Portland

Tue 1/9

5:03 p.m.-10:33 p.m.

1 stop6h 30m

C$ 800
Cheapest one-way

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Fri 3/7

7:00 a.m.-1:41 p.m.

2 stops29h 41m

C$ 463
Quickest one-way

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Fri 3/7

12:56 p.m.-9:41 p.m.

1 stop7h 45m

C$ 643

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Sorted by cheapest first

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.

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 United Airlines and Delta fly from Winnipeg to Portland, Maine in about 6h 23m. The time it takes to get you to your destination can typically vary by up to 8h 25m. 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.

See more FAQs

Travelling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway

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 Boston flights

Fly with Cheapflights

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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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