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Cheap flights from Winnipeg to Massachusetts from C$ 257

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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
21 nov. — 28 nov.1
1 adult
1 adult, Economy

Cheap flight deals from Winnipeg to Massachusetts

Keep the following information in mind while searching for Winnipeg to Massachusetts flight deals. Data was last updated 22 octubre 2025.

Round-trip from

C$ 429

One-way from

C$ 257

Popular in

December

Cheapest in

June

Average price

C$ 481
Air Canada
  • Air Canada
  • 25/11-30/11
  • 2 total stops
  • 11h 23m total
  • Winnipeg to Massachusetts
Search Deals
Air Canada
  • Air Canada
  • 5/12
  • 1 total stop
  • 6h 42m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 236 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find 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 22 octubre 2025.

mar. 25/118:15 a.m.YWG - BOS
1 stop5h 37mAir Canada
dom. 30/115:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 20/10C$ 429
vie. 5/121:45 p.m.YWG - BOS
1 stop6h 42mAir Canada
dom. 7/125:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 21/10C$ 445
vie. 21/117:05 p.m.YWG - BOS
1 stop16h 07mAir Canada
dom. 30/115:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 20/10C$ 472
sáb. 22/119:00 p.m.YWG - BOS
2 stops22h 49mMultiple Airlines
sáb. 29/119:54 p.m.BOS - YWG
1 stop18h 13mMultiple Airlines
Deal found 20/10C$ 494
sáb. 22/111:45 p.m.YWG - BOS
1 stop6h 42mAir Canada
dom. 30/115:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 20/10C$ 512
lun. 1/127:05 p.m.YWG - BOS
1 stop13h 52mAir Canada
lun. 29/125:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 20/10C$ 543
dom. 21/125:45 p.m.YWG - BOS
1 stop5h 17mDelta
mié. 31/125:45 a.m.BOS - YWG
1 stop7h 00mDelta
Deal found 21/10C$ 585
vie. 5/128:40 a.m.YWG - BOS
2 stops13h 05mUnited Airlines
dom. 7/126:00 a.m.BOS - YWG
1 stop6h 57mUnited Airlines
Deal found 21/10C$ 622
vie. 21/111:45 p.m.YWG - BOS
1 stop6h 42mAir Canada
lun. 1/125:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 20/10C$ 637
vie. 5/127:30 a.m.YWG - BOS
2 stops15h 27mMultiple Airlines
dom. 7/123:40 p.m.BOS - YWG
2 stops10h 02mMultiple Airlines
Deal found 21/10C$ 639

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 22 octubre 2025.
Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

Fly from

Winnipeg

Fly to

Massachusetts

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mar. 25/11

8:15 a.m.-2:52 p.m.

1 stop5h 37m

Boston Logan Intl

dom. 30/11

5:30 a.m.-10:16 a.m.

1 stop5h 46m

C$ 429

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

vie. 21/11

7:05 p.m.-12:12 p.m.

1 stop16h 07m

Boston Logan Intl

dom. 30/11

5:30 a.m.-10:16 a.m.

1 stop5h 46m

C$ 472

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 22/11

9:00 p.m.-8:49 p.m.

2 stops22h 49m

Boston Logan Intl

sáb. 29/11

9:54 p.m.-3:07 p.m.

1 stop18h 13m

C$ 494

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 22/11

1:45 p.m.-9:27 p.m.

1 stop6h 42m

Boston Logan Intl

dom. 30/11

5:30 a.m.-10:16 a.m.

1 stop5h 46m

C$ 512

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

dom. 21/12

5:45 p.m.-12:02 a.m.

1 stop5h 17m

Boston Logan Intl

mié. 31/12

5:45 a.m.-11:45 a.m.

1 stop7h 00m

C$ 585

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

vie. 5/12

8:40 a.m.-10:45 p.m.

2 stops13h 05m

Boston Logan Intl

dom. 7/12

6:00 a.m.-11:57 a.m.

1 stop6h 57m

C$ 622

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

mié. 25/3

2:15 p.m.-9:06 p.m.

1 stop5h 51m

Albany Intl

jue. 26/3

6:15 a.m.-11:39 a.m.

1 stop6h 24m

C$ 630

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

vie. 5/12

7:30 a.m.-11:57 p.m.

2 stops15h 27m

Boston Logan Intl

dom. 7/12

3:40 p.m.-12:42 a.m.

2 stops10h 02m

C$ 639

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

vie. 21/11

7:30 a.m.-8:49 p.m.

1 stop12h 19m

Boston Logan Intl

dom. 30/11

7:00 a.m.-10:08 a.m.

3 stops28h 08m

C$ 658

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mar. 16/12

5:45 p.m.-12:01 a.m.

1 stop5h 16m

Boston Logan Intl

sáb. 20/12

3:15 p.m.-11:44 p.m.

1 stop9h 29m

C$ 662

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/10

Showing 1-10 of 20 results
1
2

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$ 229). Flying from Winnipeg to Massachusetts in December is currently the most expensive (average of C$ 502). 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.

What is the cheapest time of day to fly from YWG to MA?

Find hourly flight availability from Winnipeg to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 22 octubre 2025.

It’s typically best to fly out from Winnipeg to Massachusetts in the morning. Doing so could potentially save you 65% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 22 octubre 2025.
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
382 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
382 reviews
Porter Airlines
8.0
Very good
382 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,988 reviews
Porter Airlines
8.0
Very good
382 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
WestJet
7.2
Good
3,132 reviews
Porter Airlines
8.0
Very good
382 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,335 reviews
Porter Airlines
8.0
Very good
382 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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 37m. 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, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 229). Flying from Winnipeg to Massachusetts in December is currently the most expensive (average of C$ 502). 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 22 octubre 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 242AverageC$ 406FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 349AverageC$ 503FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 419AverageC$ 628FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 481AverageC$ 1,153FlexibilityNo 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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