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Cheap flights from Winnipeg to Massachusetts from C$ 241

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 15/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
13 Jun — 20 Jun1
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 14 May 2026.

Wed 3/611:40 a.m.
YWG
-
BOS
1 stop6h 25m
Porter Airlines
Wed 10/610:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 10/5C$ 378
Sat 17/108:00 a.m.
YWG
-
BOS
1 stop10h 11m
Delta
Wed 21/106:00 p.m.
BOS
-
YWG
1 stop6h 34m
Delta
Deal found 11/5C$ 382
Tue 21/79:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Wed 29/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 11/5C$ 400
Sat 17/1012:20 p.m.
YWG
-
BOS
2 stops8h 07m
Air Canada
Wed 21/1010:50 a.m.
BOS
-
YWG
1 stop6h 27m
Air Canada
Deal found 11/5C$ 403
Tue 4/89:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Thu 6/810:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 12/5C$ 407
Sat 1/89:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Sun 9/810:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 11/5C$ 408
Thu 23/79:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Thu 30/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 11/5C$ 415
Wed 22/79:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Wed 29/77:10 a.m.
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Deal found 11/5C$ 422
Sat 25/79:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Wed 29/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 11/5C$ 429
Tue 22/98:50 a.m.
YWG
-
ALB
2 stops13h 02m
Delta
Fri 25/99:50 a.m.
ALB
-
YWG
2 stops14h 37m
Delta
Deal found 12/5C$ 516
Tue 7/77:00 a.m.
YWG
-
ALB
2 stops15h 21m
WestJet
Tue 21/76:05 a.m.
ALB
-
YWG
2 stops19h 50m
WestJet
Deal found 13/5C$ 534
Sat 11/76:15 a.m.
YWG
-
ALB
2 stops16h 06m
WestJet
Fri 4/96:00 a.m.
ALB
-
YWG
2 stops19h 55m
WestJet
Deal found 12/5C$ 545

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 14 May 2026.

Round-trip from

C$ 378

One-way from

C$ 241

Popular in

January

Cheapest in

June

Average price

C$ 992
Porter Airlines
  • Porter Airlines
  • 3/6-10/6
  • 2 total stops
  • 12h 39m total
  • Winnipeg to Massachusetts
Search Deals
Porter Airlines
  • Porter Airlines
  • 14/7
  • 1 total stop
  • 7h 15m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 155 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 14 May 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

Wed 3/6

11:40 a.m.-7:05 p.m.

1 stop6h 25m

Boston Logan Intl

Wed 10/6

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

1 stop6h 14m

C$ 378

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 17/10

8:00 a.m.-7:11 p.m.

1 stop10h 11m

Boston Logan Intl

Wed 21/10

6:00 p.m.-11:34 p.m.

1 stop6h 34m

C$ 382

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 20/7

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

1 stop7h 15m

Boston Logan Intl

Fri 24/7

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

1 stop6h 14m

C$ 415

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 21/7

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

1 stop7h 15m

Boston Logan Intl

Sat 25/7

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

2 stops11h 48m

C$ 475

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 22/9

8:50 a.m.-10:52 p.m.

2 stops13h 02m

Albany Intl

Fri 25/9

9:50 a.m.-11:27 p.m.

2 stops14h 37m

C$ 516

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 11/7

6:15 a.m.-11:21 p.m.

2 stops16h 06m

Albany Intl

Fri 4/9

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

2 stops19h 55m

C$ 547

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 4/8

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

1 stop7h 15m

Boston Logan Intl

Sun 9/8

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

2 stops8h 53m

C$ 571

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 3/8

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

1 stop7h 15m

Boston Logan Intl

Sun 9/8

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

1 stop6h 14m

C$ 600

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 22/9

2:05 p.m.-9:39 a.m.

2 stops18h 34m

Albany Intl

Fri 25/9

4:30 p.m.-10:24 p.m.

1 stop6h 54m

C$ 601

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 3/8

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

2 stops10h 35m

Boston Logan Intl

Fri 7/8

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

1 stop6h 14m

C$ 601

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/5

Showing 1-10 of 25 resultsSorted by cheapest first
1
2
3

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

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

To ensure you get the cheapest price possible for a flight from Winnipeg to Massachusetts, you should look to book at least 15 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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$ 1,071). 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 14 May 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
436 reviews
Check prices

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

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
436 reviews
Porter Airlines
8.0
Very good
436 reviews
Check prices

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

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
9,711 reviews
Porter Airlines
8.0
Very good
436 reviews
Check prices

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

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
3,334 reviews
Porter Airlines
8.0
Very good
436 reviews
Check prices

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

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
11,029 reviews
Porter Airlines
8.0
Very good
436 reviews
Check prices

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

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 25m. Fly via Porter Airlines, Delta, or WestJet 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$ 1,071). 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 14 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 214AverageC$ 407FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 321AverageC$ 589FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 389AverageC$ 611FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 470AverageC$ 1,125FlexibilityNo cancel feeOn-time60%
Search WestJet 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 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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