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Cheap flights from Winnipeg to Massachusetts from C$ 233

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
7 Sep — 14 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 8 August 2026.

Sat 19/95:00 a.m. -
1 stop5h 51m
Sat 26/93:35 p.m. -
1 stop6h 39m
Deal found 7/8C$ 400
Thu 3/95:00 a.m. -
1 stop5h 47m
Thu 10/910:50 a.m. -
1 stop8h 22m
Deal found 6/8C$ 407
Fri 16/102:05 p.m. -
1 stop7h 35m
Fri 23/105:50 a.m. -
1 stop7h 39m
Deal found 7/8C$ 419
Fri 2/109:20 a.m. -
1 stop8h 15m
Mon 5/1010:05 a.m. -
1 stop6h 14m
Deal found 7/8C$ 422
Wed 30/95:00 a.m. -
1 stop5h 51m
Mon 5/106:00 a.m. -
1 stop6h 12m
Deal found 7/8C$ 426
Fri 16/109:20 a.m. -
1 stop8h 15m
Fri 23/107:00 a.m. -
2 stops11h 58m
Deal found 7/8C$ 431
Fri 6/115:15 a.m. -
1 stop11h 43m
Mon 9/115:30 a.m. -
1 stop5h 35m
Deal found 6/8C$ 433
Fri 28/87:45 p.m. -
1 stop15h 07m
Wed 23/910:50 a.m. -
1 stop6h 37m
Deal found 7/8C$ 440
Tue 1/912:15 p.m. -
1 stop5h 20m
Tue 8/910:05 a.m. -
1 stop6h 14m
Deal found 4/8C$ 445
Fri 6/1111:35 a.m. -
2 stops9h 42m
Mon 9/118:00 a.m. -
2 stops11h 10m
Deal found 6/8C$ 452
Sat 19/911:15 a.m. -
2 stops22h 15m
Sat 26/910:05 a.m. -
1 stop15h 50m
Deal found 7/8C$ 454
Thu 22/108:10 a.m. -
1 stop5h 31m
Sun 25/105:30 a.m. -
1 stop6h 50m
Deal found 4/8C$ 460

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 8 August 2026.

Round-trip from

C$ 400

One-way from

C$ 233

Popular in

April

Cheapest in

August

Average price

C$ 481
Air Canada
  • Air Canada
  • 19/9-26/9
  • 2 total stops
  • 12h 30m total
  • Winnipeg to Massachusetts
Search Deals
7/10
  • 7/10
  • 1 total stop
  • 9h 31m 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 8 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
Quickest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 22/10

8:10 a.m.-2:41 p.m.

1 stop5h 31m

Boston Logan Intl

Sun 25/10

5:30 a.m.-11:20 a.m.

1 stop6h 50m

C$ 460

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 3/9

2:00 p.m.-1:11 a.m.

1 stop10h 11m

Boston Logan Intl

Thu 10/9

9:30 a.m.-10:33 p.m.

2 stops14h 03m

C$ 471

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 19/9

2:00 p.m.-11:59 p.m.

2 stops8h 59m

Boston Logan Intl

Sat 26/9

8:00 a.m.-8:57 p.m.

2 stops13h 57m

C$ 471

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 2/10

7:00 a.m.-12:54 a.m.

1 stop16h 54m

Boston Logan Intl

Mon 5/10

7:01 a.m.-10:33 p.m.

1 stop16h 32m

C$ 471

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 17/9

2:00 p.m.-1:10 a.m.

1 stop10h 10m

Boston Logan Intl

Sat 19/9

8:21 p.m.-11:52 a.m.

1 stop16h 31m

C$ 471

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$ 471

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 10/9

7:45 a.m.-6:35 p.m.

1 stop9h 50m

Boston Logan Intl

Mon 14/9

7:30 p.m.-12:55 a.m.

1 stop6h 25m

C$ 477

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$ 485

WinnipegAlbany

YWG Winnipeg - ALB Albany Intl

YWGALB

Winnipeg

Tue 27/10

8:40 a.m.-11:30 p.m.

1 stop13h 50m

Albany Intl

Sat 31/10

7:32 a.m.-8:57 p.m.

1 stop14h 25m

C$ 804

WinnipegAlbany

YWG Winnipeg - ALB Albany Intl

YWGALB

Winnipeg

Mon 26/10

8:40 a.m.-11:30 p.m.

1 stop13h 50m

Albany Intl

Fri 30/10

7:35 p.m.-12:23 p.m.

2 stops17h 48m

C$ 867

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

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$ 487). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,279). 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 below average for this route at the moment.
Winnipeg to Massachusetts flights typically cost between C$ 449 and C$ 605 in September.
The cheapest round-trip price found within the last 5 days was C$ 400 on Air Canada (19 Sep-26 Sep).

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 8 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
450 reviews
Check prices

Boarding

8.2

Crew

8.6

Food

7.5

Entertainment

6.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Porter Airlines
8.0
Very good
450 reviews
Porter Airlines
8.0
Very good
450 reviews
Check prices

Boarding

8.2

Crew

8.6

Food

7.5

Entertainment

6.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
United Airlines
7.4
Good
10,084 reviews
Porter Airlines
8.0
Very good
450 reviews
Check prices

Boarding

8.2

Crew

8.6

Food

7.5

Entertainment

6.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Air Canada
7.1
Good
11,450 reviews
Porter Airlines
8.0
Very good
450 reviews
Check prices

Boarding

8.2

Crew

8.6

Food

7.5

Entertainment

6.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

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 5h 31m. Fly via 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, August is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 487). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,279). 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 8 August 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 162AverageC$ 626FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 327AverageC$ 476FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 397AverageC$ 626FlexibilityNo 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.

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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