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Cheap flights from Winnipeg to Massachusetts from C$ 266

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 26/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
17 May — 24 May1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Massachusetts

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Massachusetts
Explore the most affordable flight options available from Winnipeg to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 April 2026.

Fri 28/89:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Mon 31/810:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 15/4C$ 402
Tue 29/99:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Sun 4/1010:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 17/4C$ 403
Sat 1/83:20 p.m.
YWG
-
BOS
1 stop6h 18m
Air Canada
Thu 6/810:40 a.m.
BOS
-
YWG
1 stop5h 34m
Air Canada
Deal found 13/4C$ 407
Sat 1/83:20 p.m.
YWG
-
BOS
1 stop6h 18m
Air Canada
Sat 8/86:00 a.m.
BOS
-
YWG
1 stop6h 15m
Air Canada
Deal found 13/4C$ 414
Sat 1/83:20 p.m.
YWG
-
BOS
1 stop6h 18m
Air Canada
Fri 7/86:00 a.m.
BOS
-
YWG
1 stop6h 15m
Air Canada
Deal found 13/4C$ 416
Fri 31/77:10 p.m.
YWG
-
BOS
1 stop12h 34m
Air Canada
Thu 6/810:40 a.m.
BOS
-
YWG
1 stop5h 34m
Air Canada
Deal found 13/4C$ 429
Thu 27/89:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Sun 30/810:05 a.m.
BOS
-
YWG
2 stops8h 53m
Porter Airlines
Deal found 14/4C$ 432
Fri 31/77:10 p.m.
YWG
-
BOS
1 stop12h 34m
Air Canada
Sat 8/86:00 a.m.
BOS
-
YWG
1 stop6h 15m
Air Canada
Deal found 13/4C$ 436
Thu 7/55:10 a.m.
YWG
-
BOS
2 stops8h 37m
Air Canada
Wed 13/55:10 a.m.
BOS
-
YWG
1 stop6h 58m
Air Canada
Deal found 16/4C$ 455
Fri 29/59:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Mon 1/610:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 15/4C$ 468
Sat 23/52:00 p.m.
YWG
-
ALB
2 stops19h 11m
United Airlines
Wed 27/54:43 p.m.
ALB
-
YWG
1 stop6h 50m
United Airlines
Deal found 12/4C$ 472
Wed 6/52:00 p.m.
YWG
-
ALB
1 stop6h 12m
United Airlines
Wed 13/56:00 a.m.
ALB
-
YWG
1 stop6h 52m
United Airlines
Deal found 16/4C$ 473

Find flight deals from Winnipeg to Massachusetts

Keep the following information in mind while searching for Winnipeg to Massachusetts flight deals. Data was last updated 17 April 2026.

Round-trip from

C$ 402

One-way from

C$ 266

Popular in

April

Cheapest in

June

Average price

C$ 1,081
Porter Airlines
  • Porter Airlines
  • 28/8-31/8
  • 2 total stops
  • 13h 29m total
  • Winnipeg to Massachusetts
Search Deals
WestJet
  • WestJet
  • 26/5
  • 1 total stop
  • 9h 40m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 209 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Massachusetts 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 17 April 2026.
Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 1/8

3:20 p.m.-10:38 p.m.

1 stop6h 18m

Boston Logan Intl

Sat 8/8

6:00 a.m.-11:15 a.m.

1 stop6h 15m

C$ 414

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 27/8

9:20 a.m.-5:35 p.m.

1 stop7h 15m

Boston Logan Intl

Sun 30/8

10:05 a.m.-5:58 p.m.

2 stops8h 53m

C$ 432

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 23/5

7:00 a.m.-2:21 p.m.

1 stop6h 21m

Albany Intl

Wed 27/5

4:43 p.m.-10:33 p.m.

1 stop6h 50m

C$ 472

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 26/5

9:20 a.m.-5:35 p.m.

1 stop7h 15m

Boston Logan Intl

Sat 30/5

7:10 a.m.-6:03 p.m.

2 stops11h 53m

C$ 481

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 2/6

9:20 a.m.-5:35 p.m.

1 stop7h 15m

Boston Logan Intl

Tue 9/6

10:05 a.m.-5:58 p.m.

2 stops8h 53m

C$ 483

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 2/6

7:00 a.m.-5:40 p.m.

1 stop9h 40m

Boston Logan Intl

Tue 9/6

6:30 p.m.-11:10 a.m.

1 stop17h 40m

C$ 507

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 26/5

5:10 a.m.-2:47 p.m.

2 stops8h 37m

Boston Logan Intl

Sat 30/5

5:10 a.m.-11:08 a.m.

1 stop6h 58m

C$ 509

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 30/5

9:20 a.m.-8:55 p.m.

2 stops10h 35m

Boston Logan Intl

Sat 6/6

7:10 a.m.-5:58 p.m.

2 stops11h 48m

C$ 509

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 23/5

9:20 a.m.-8:55 p.m.

2 stops10h 35m

Boston Logan Intl

Sun 7/6

10:05 a.m.-3:19 p.m.

1 stop6h 14m

C$ 509

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 11/7

6:15 a.m.-11:06 p.m.

2 stops15h 51m

Albany Intl

Fri 4/9

6:00 a.m.-12:55 a.m.

2 stops19h 55m

C$ 528

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/4

Showing 1-10 of 35 resultsSorted by cheapest first
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Best time to book a flight from Winnipeg to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts 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 Massachusetts

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

Currently, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 137). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 1,073). 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.

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

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated 17 April 2026.
Read through reviews of airlines operating flights from Winnipeg to Massachusetts, such as Porter Airlines,United Airlines, andWestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
435 reviews
Check prices

Crew

8.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
435 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Crew

8.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,600 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Crew

8.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
WestJet
7.2
Good
3,321 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Crew

8.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,931 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Crew

8.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Massachusetts?

    Located just 7.3 km from the city centre, Winnipeg (YWG) is the airport most travellers will use when flying to Massachusetts from Winnipeg.

  • How long is the flight from Winnipeg to Massachusetts?

    There are many flights that can get you from Winnipeg to Massachusetts in 6h 18m. Fly via Porter Airlines, Air Canada, or United Airlines to get the fastest option. The distance between Winnipeg and Massachusetts is about 2173 km. This flight may include one or multiple stops.

  • What are the most popular routes from Winnipeg to Massachusetts?

    The most popular flight routes from Winnipeg to Massachusetts are Winnipeg - Boston Logan Intl, Winnipeg - Albany Intl and Winnipeg - Provincetown.

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

    Yes. In addition to deals on Winnipeg to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Massachusetts.

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

    Yes. Cheapflights offers flight deals from Winnipeg to Massachusetts 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 Massachusetts?

    Currently, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 137). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 1,073). 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

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Top 4 airlines flying from Winnipeg to Massachusetts

Discover the top 4 airlines that operate flights from Winnipeg to Massachusetts. 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 17 April 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 214AverageC$ 396FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 302AverageC$ 590FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 321AverageC$ 594FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 470AverageC$ 1,126FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Winnipeg to Massachusetts?

Cheapflights helps you search for flights from Winnipeg to Massachusetts 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 Massachusetts?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Winnipeg to Massachusetts for you. Better yet — we are completely free to use.

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

Need flexible booking options for your flight to Massachusetts 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 Massachusetts 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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