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Cheap flights from Winnipeg to Portland, ME from C$ 331

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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PWM
25 May — 1 Jun1
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 25 April 2026.

Sat 23/56:00 a.m.
YWG
-
PWM
2 stops28h 55m
WestJet
Sat 30/512:50 p.m.
PWM
-
YWG
2 stops13h 05m
WestJet
Deal found 23/4C$ 553
Sat 24/1010:45 a.m.
YWG
-
PWM
2 stops24h 08m
WestJet
Wed 28/1011:30 a.m.
PWM
-
YWG
1 stop13h 04m
WestJet
Deal found 20/4C$ 556
Sat 30/52:00 p.m.
YWG
-
PWM
2 stops18h 11m
Air Canada
Sat 6/66:00 a.m.
PWM
-
YWG
2 stops18h 18m
Air Canada
Deal found 23/4C$ 561
Sat 6/61:25 p.m.
YWG
-
PWM
2 stops9h 05m
Air Canada
Wed 10/66:00 a.m.
PWM
-
YWG
2 stops18h 18m
Air Canada
Deal found 23/4C$ 599
Thu 21/53:15 p.m.
YWG
-
PWM
2 stops47h 52m
WestJet
Fri 29/512:50 p.m.
PWM
-
YWG
2 stops13h 05m
WestJet
Deal found 23/4C$ 604
Sun 24/55:10 a.m.
YWG
-
PWM
2 stops17h 20m
Air Canada
Wed 27/53:16 p.m.
PWM
-
YWG
2 stops19h 53m
Air Canada
Deal found 23/4C$ 613
Sat 6/66:15 a.m.
YWG
-
PWM
2 stops8h 52m
WestJet
Wed 10/611:48 a.m.
PWM
-
YWG
1 stop6h 04m
WestJet
Deal found 23/4C$ 619
Wed 20/510:45 a.m.
YWG
-
PWM
2 stops11h 33m
WestJet
Fri 29/512:50 p.m.
PWM
-
YWG
2 stops13h 05m
WestJet
Deal found 23/4C$ 621
Sat 20/66:00 a.m.
YWG
-
PWM
2 stops33h 00m
WestJet
Thu 25/611:48 a.m.
PWM
-
YWG
2 stops10h 52m
WestJet
Deal found 25/4C$ 625
Sun 24/55:41 p.m.
YWG
-
PWM
2 stops17h 57m
Delta
Thu 28/55:51 p.m.
PWM
-
YWG
2 stops18h 03m
Delta
Deal found 23/4C$ 632
Wed 20/56:40 a.m.
YWG
-
PWM
2 stops15h 32m
Delta
Thu 28/55:51 p.m.
PWM
-
YWG
2 stops18h 03m
Delta
Deal found 23/4C$ 645

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 25 April 2026.

Round-trip from

C$ 553

One-way from

C$ 331
WestJet
  • WestJet
  • 23/5-28/5
  • 4 total stops
  • 62h 02m total
  • Winnipeg to Portland
Search Deals
8/6
  • 8/6
  • 3 total stops
  • 17h 54m 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 25 April 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

Sat 6/6

1:25 p.m.-11:30 p.m.

2 stops9h 05m

Portland

Wed 10/6

6:00 a.m.-11:18 p.m.

2 stops18h 18m

C$ 599

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Sat 6/6

6:15 a.m.-4:07 p.m.

2 stops8h 52m

Portland

Wed 10/6

11:48 a.m.-4:52 p.m.

1 stop6h 04m

C$ 619

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Sat 6/6

7:00 a.m.-9:51 p.m.

1 stop13h 51m

Portland

Wed 10/6

6:00 a.m.-10:33 p.m.

1 stop17h 33m

C$ 724

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Thu 21/5

7:00 a.m.-2:26 p.m.

1 stop6h 26m

Portland

Fri 29/5

6:00 a.m.-10:38 p.m.

1 stop17h 38m

C$ 725

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Sun 24/5

7:00 a.m.-2:26 p.m.

1 stop6h 26m

Portland

Thu 28/5

6:00 a.m.-11:52 a.m.

1 stop6h 52m

C$ 734
Quickest round-trip

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Fri 22/5

7:00 a.m.-2:26 p.m.

1 stop6h 26m

Portland

Fri 29/5

4:56 p.m.-10:38 p.m.

1 stop6h 42m

C$ 768

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Wed 20/5

5:10 a.m.-6:23 p.m.

2 stops12h 13m

Portland

Sat 30/5

6:00 a.m.-11:52 a.m.

1 stop6h 52m

C$ 776

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Fri 22/5

7:00 a.m.-2:26 p.m.

1 stop6h 26m

Portland

Wed 27/5

4:56 p.m.-10:38 p.m.

1 stop6h 42m

C$ 838

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Fri 22/5

8:10 a.m.-11:51 p.m.

2 stops14h 41m

Portland

Sun 31/5

5:15 a.m.-9:28 p.m.

2 stops17h 13m

C$ 854
Cheapest one-way

WinnipegPortland

YWG - PWM

YWGPWM

Winnipeg

Mon 8/6

9:05 p.m.-3:59 p.m.

3 stops17h 54m

C$ 331

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/4

Showing 1-10 of 16 resultsSorted by cheapest first
1
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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 Air Canada, WestJet, and United Airlines fly from Winnipeg to Portland, Maine in about 8h 52m. The time it takes to get you to your destination can typically vary by up to 4h 59m. 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

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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