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Cheap flights from Winnipeg to Massachusetts from C$ 237

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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
12 Sep — 19 Sep1
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 13 August 2026.

Sat 26/96:00 a.m. -
1 stop10h 40m
Sat 3/106:30 p.m. -
1 stop18h 45m
Deal found 12/8C$ 453
Fri 9/107:10 p.m. -
1 stop21h 30m
Sun 18/106:30 p.m. -
1 stop17h 40m
Deal found 9/8C$ 470
Fri 25/911:15 a.m. -
2 stops22h 15m
Wed 30/97:30 p.m. -
1 stop15h 15m
Deal found 9/8C$ 471
Thu 10/911:15 a.m. -
2 stops22h 15m
Thu 17/910:05 a.m. -
1 stop24h 40m
Deal found 8/8C$ 474
Thu 17/96:15 a.m. -
1 stop11h 20m
Mon 21/97:30 p.m. -
1 stop6h 25m
Deal found 10/8C$ 477
Sat 12/911:15 a.m. -
2 stops22h 15m
Sat 10/1010:05 a.m. -
1 stop6h 14m
Deal found 8/8C$ 481
Fri 2/106:00 a.m. -
2 stops34h 40m
Mon 5/106:30 p.m. -
2 stops21h 10m
Deal found 13/8C$ 482
Thu 1/102:05 p.m. -
1 stop7h 35m
Sun 4/106:00 a.m. -
1 stop6h 12m
Deal found 9/8C$ 493
Wed 9/911:15 a.m. -
2 stops22h 15m
Sun 13/97:30 p.m. -
1 stop15h 15m
Deal found 9/8C$ 496
Sun 6/97:00 a.m. -
1 stop15h 06m
Sun 13/96:00 a.m. -
1 stop6h 52m
Deal found 9/8C$ 746
Tue 27/102:15 p.m. -
1 stop6h 18m
Sat 31/108:40 a.m. -
2 stops13h 17m
Deal found 12/8C$ 751
Sun 6/97:00 a.m. -
2 stops15h 05m
Sun 13/96:00 a.m. -
2 stops30h 10m
Deal found 9/8C$ 810

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 13 August 2026.

Round-trip from

C$ 453

One-way from

C$ 237

Popular in

April

Cheapest in

August

Average price

C$ 485
WestJet
  • WestJet
  • 26/9-3/10
  • 2 total stops
  • 31h 15m total
  • Winnipeg to Massachusetts
Search Deals
Porter Airlines
  • Porter Airlines
  • 7/10
  • 1 total stop
  • 8h 15m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 205 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 67 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 13 August 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

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 10/9

11:15 a.m.-10:30 a.m.

2 stops22h 15m

Boston Logan Intl

Thu 17/9

10:05 a.m.-9:45 a.m.

1 stop24h 40m

C$ 474

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 16/10

9:05 p.m.-5:40 p.m.

1 stop19h 35m

Boston Logan Intl

Fri 23/10

6:30 p.m.-2:05 p.m.

1 stop20h 35m

C$ 481

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 12/9

11:15 a.m.-10:30 a.m.

2 stops22h 15m

Boston Logan Intl

Sat 10/10

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

1 stop6h 14m

C$ 481

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 26/9

6:00 a.m.-5:40 p.m.

1 stop10h 40m

Boston Logan Intl

Sat 3/10

6:30 p.m.-9:35 a.m.

2 stops16h 05m

C$ 484

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 11/9

11:15 a.m.-10:40 p.m.

2 stops10h 25m

Boston Logan Intl

Fri 18/9

3:35 p.m.-9:45 a.m.

2 stops19h 10m

C$ 527

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 8/12

6:35 a.m.-4:46 p.m.

1 stop9h 11m

Boston Logan Intl

Wed 9/12

6:15 p.m.-11:29 p.m.

1 stop6h 14m

C$ 545
Quickest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 2/9

7:00 a.m.-4:27 p.m.

1 stop8h 27m

Boston Logan Intl

Sat 5/9

6:01 a.m.-11:52 a.m.

1 stop6h 51m

C$ 562

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 19/9

6:15 a.m.-5:25 p.m.

1 stop10h 10m

Boston Logan Intl

Mon 21/9

4:30 p.m.-12:55 a.m.

1 stop9h 25m

C$ 567

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 2/9

12:15 p.m.-6:35 p.m.

1 stop5h 20m

Boston Logan Intl

Sat 5/9

7:00 a.m.-5:58 p.m.

2 stops11h 58m

C$ 576

WinnipegAlbany

YWG Winnipeg - ALB Albany Intl

YWGALB

Winnipeg

Sun 6/9

7:00 a.m.-11:06 p.m.

1 stop15h 06m

Albany Intl

Sun 13/9

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

1 stop6h 52m

C$ 746

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/8

Showing 1-10 of 22 resultsSorted by cheapest first
1
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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

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

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 485). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,276). 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?

Airfare is typical for this route at the moment.
Winnipeg to Massachusetts flights typically cost between C$ 449 and C$ 625 in September.
The cheapest round-trip price found within the last 5 days was C$ 453 on WestJet (26 Sep-3 Oct).

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 13 August 2026.
Read through reviews of airlines operating flights from Winnipeg to Massachusetts, such as Porter Airlines,United Airlines, andAir Canada. 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
456 reviews
Check prices

Crew

8.6

Food

7.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
456 reviews
Porter Airlines
8.0
Very good
456 reviews
Check prices

Crew

8.6

Food

7.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
United Airlines
7.4
Good
10,112 reviews
Porter Airlines
8.0
Very good
456 reviews
Check prices

Crew

8.6

Food

7.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Canada
7.1
Good
11,466 reviews
Porter Airlines
8.0
Very good
456 reviews
Check prices

Crew

8.6

Food

7.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

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 15h 06m. Fly via WestJet, Porter Airlines, or Air Canada to get the fastest option. The distance between Winnipeg and Massachusetts is about 1955 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, August is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 485). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,276). 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 3 airlines flying from Winnipeg to Massachusetts

Discover the top 3 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 13 August 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 162AverageC$ 624FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 326AverageC$ 474FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 396AverageC$ 622FlexibilityNo cancel feeOn-time67%
Search Air Canada 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.

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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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