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Cheap flights from Winnipeg to Massachusetts from C$ 182

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 30/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
15 Jan — 22 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Massachusetts

Enter your travel dates to find the best prices.

Best flights from Winnipeg to Massachusetts
Discover carefully curated flight deals from Winnipeg to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 16 December 2025.

Mon 12/18:00 a.m.YWG - BOS
1 stop14h 57mMultiple Airlines
Mon 19/15:34 a.m.BOS - YWG
1 stop13h 29mMultiple Airlines
Deal found 14/12C$ 362
Thu 15/18:15 a.m.YWG - BOS
1 stop5h 37mAir Canada
Thu 22/110:15 a.m.BOS - YWG
1 stop7h 20mAir Canada
Deal found 16/12C$ 438
Mon 2/32:20 p.m.YWG - ALB
1 stop5h 56mUnited Airlines
Wed 4/37:30 p.m.ALB - YWG
2 stops17h 27mUnited Airlines
Deal found 14/12C$ 486
Fri 30/112:55 p.m.YWG - BOS
2 stops35h 18mMultiple Airlines
Fri 6/26:00 a.m.BOS - YWG
1 stop10h 09mMultiple Airlines
Deal found 16/12C$ 399
Fri 13/28:15 a.m.YWG - BOS
1 stop5h 37mAir Canada
Sun 15/25:30 a.m.BOS - YWG
1 stop5h 45mAir Canada
Deal found 15/12C$ 453
Thu 15/15:00 a.m.YWG - BOS
1 stop29h 05mMultiple Airlines
Thu 22/16:00 a.m.BOS - YWG
2 stops19h 41mMultiple Airlines
Deal found 16/12C$ 424

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 16 December 2025.

Round-trip from

C$ 362

One-way from

C$ 182

Popular in

December

Cheapest in

June

Average price

C$ 802
12/1-19/1
  • 12/1-19/1
  • 2 total stops
  • 28h 26m total
  • Winnipeg to Massachusetts
Search Deals
30/1
  • 30/1
  • 3 total stops
  • 29h 18m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 21% potential increase in price (C$ 211 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 16 December 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

Mon 12/1

8:00 a.m.-11:57 p.m.

1 stop14h 57m

Boston Logan Intl

Mon 19/1

5:34 a.m.-6:03 p.m.

1 stop13h 29m

C$ 362

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 30/1

12:55 p.m.-1:13 a.m.

2 stops35h 18m

Boston Logan Intl

Fri 6/2

6:00 a.m.-3:09 p.m.

1 stop10h 09m

C$ 399

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 15/1

5:00 a.m.-11:05 a.m.

1 stop29h 05m

Boston Logan Intl

Thu 22/1

6:00 a.m.-12:41 a.m.

2 stops19h 41m

C$ 424

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 15/1

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

1 stop5h 37m

Boston Logan Intl

Thu 22/1

10:15 a.m.-4:35 p.m.

1 stop7h 20m

C$ 438

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 13/2

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

1 stop5h 37m

Boston Logan Intl

Sun 15/2

5:30 a.m.-10:15 a.m.

1 stop5h 45m

C$ 453

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Mon 2/3

2:20 p.m.-9:16 p.m.

1 stop5h 56m

Albany Intl

Wed 4/3

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

2 stops17h 27m

C$ 486

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 30/1

6:55 p.m.-1:13 a.m.

3 stops29h 18m

C$ 182

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 4/6

11:45 a.m.-6:28 p.m.

1 stop5h 43m

C$ 321

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 3/6

11:45 a.m.-6:28 p.m.

1 stop5h 43m

C$ 321

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 4/6

7:00 a.m.-11:59 p.m.

2 stops15h 59m

C$ 332

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/12

Showing 1-10 of 12 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$ 222). Flying from Winnipeg to Massachusetts in March is currently the most expensive (average of C$ 451). 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 16 December 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 16 December 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
399 reviews
Check prices

Crew

8.6

Entertainment

7.0

Comfort

7.9

Food

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
399 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Crew

8.6

Entertainment

7.0

Comfort

7.9

Food

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,094 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Crew

8.6

Entertainment

7.0

Comfort

7.9

Food

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
WestJet
7.2
Good
3,202 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Crew

8.6

Entertainment

7.0

Comfort

7.9

Food

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,531 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Crew

8.6

Entertainment

7.0

Comfort

7.9

Food

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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, United Airlines, 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$ 222). Flying from Winnipeg to Massachusetts in March is currently the most expensive (average of C$ 451). 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 16 December 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 237AverageC$ 399FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 349AverageC$ 502FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 421AverageC$ 632FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 472AverageC$ 1,130FlexibilityNo 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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