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Cheap flights from Winnipeg to Massachusetts from C$ 340

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 30/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
7 Jan — 14 Jan1
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 December 2025.

Sat 20/127:05 p.m.YWG - BOS
1 stop13h 52mAir Canada
Thu 1/110:15 a.m.BOS - YWG
1 stop7h 20mAir Canada
Deal found 6/12C$ 761
Sat 20/128:40 a.m.YWG - BOS
2 stops25h 28mUnited Airlines
Thu 1/16:15 a.m.BOS - YWG
1 stop7h 24mUnited Airlines
Deal found 6/12C$ 912
Thu 18/126:00 a.m.YWG - BOS
2 stops15h 55mAmerican Airlines
Sat 3/12:15 p.m.BOS - YWG
2 stops10h 20mAmerican Airlines
Deal found 7/12C$ 933
Thu 18/121:30 p.m.YWG - BOS
1 stop8h 07mUnited Airlines
Sat 3/12:15 p.m.BOS - YWG
2 stops22h 42mUnited Airlines
Deal found 7/12C$ 957
Sat 20/126:00 a.m.YWG - BOS
2 stops15h 55mAmerican Airlines
Thu 1/110:40 a.m.BOS - YWG
2 stops13h 55mAmerican Airlines
Deal found 6/12C$ 982
Thu 18/128:20 p.m.YWG - BOS
1 stop12h 15mMultiple Airlines
Sat 3/17:05 a.m.BOS - YWG
1 stop17h 30mMultiple Airlines
Deal found 7/12C$ 988
Mon 8/125:45 p.m.YWG - BOS
1 stop5h 16mMultiple Airlines
Mon 15/1211:23 a.m.BOS - YWG
2 stops33h 43mMultiple Airlines
Deal found 7/12C$ 1,018
Sat 13/122:20 p.m.YWG - BOS
1 stop6h 25mUnited Airlines
Sat 20/127:36 p.m.BOS - YWG
2 stops17h 21mUnited Airlines
Deal found 7/12C$ 1,109

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 December 2025.

Round-trip from

C$ 450

One-way from

C$ 340

Popular in

December

Cheapest in

June

Average price

C$ 770
11/3-20/3
  • 11/3-20/3
  • 2 total stops
  • 26h 43m total
  • Winnipeg to Massachusetts
Search Deals
Air Canada
  • Air Canada
  • 30/4
  • 1 total stop
  • 5h 37m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 20% potential increase in price (C$ 201 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 26 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 8 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

Wed 11/3

7:30 a.m.-1:04 a.m.

1 stop16h 34m

Boston Logan Intl

Fri 20/3

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

1 stop10h 09m

C$ 450

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Mon 2/3

2:20 p.m.-9:21 p.m.

1 stop6h 01m

Albany Intl

Wed 4/3

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

2 stops17h 27m

C$ 488

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 20/1

9:00 p.m.-4:19 p.m.

3 stops18h 19m

Boston Logan Intl

Tue 27/1

3:43 p.m.-9:49 a.m.

2 stops19h 06m

C$ 506

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 15/1

9:00 p.m.-11:19 p.m.

3 stops25h 19m

Boston Logan Intl

Mon 19/1

5:23 p.m.-12:41 a.m.

3 stops32h 18m

C$ 528

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 13/3

7:30 a.m.-1:04 a.m.

1 stop16h 34m

Boston Logan Intl

Mon 16/3

3:30 p.m.-12:39 a.m.

2 stops10h 09m

C$ 580

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 13/3

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

1 stop5h 37m

Boston Logan Intl

Mon 16/3

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

1 stop5h 45m

C$ 612

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 2/2

2:20 p.m.-9:38 p.m.

1 stop6h 18m

Boston Logan Intl

Tue 3/2

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

1 stop6h 57m

C$ 616

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 15/1

2:20 p.m.-11:49 p.m.

2 stops8h 29m

Boston Logan Intl

Mon 19/1

6:17 p.m.-11:57 a.m.

2 stops18h 40m

C$ 616

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 11/3

2:20 p.m.-11:57 p.m.

2 stops8h 37m

Boston Logan Intl

Fri 20/3

6:30 p.m.-11:57 a.m.

2 stops18h 27m

C$ 616

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 30/4

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

1 stop5h 37m

C$ 340

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/12

Showing 1-10 of 17 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$ 453). 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 8 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 8 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
397 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.6

Entertainment

7.0

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
397 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.6

Entertainment

7.0

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
9,079 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.6

Entertainment

7.0

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
3,193 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.6

Entertainment

7.0

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
10,512 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.6

Entertainment

7.0

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 6h 01m. Fly via United Airlines to get the fastest option. The distance between Winnipeg and Massachusetts is about 1955 km.

  • 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$ 453). 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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Alternative routes for Winnipeg to Massachusetts

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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 8 December 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 238AverageC$ 400FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 344AverageC$ 491FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 413AverageC$ 634FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 474AverageC$ 1,135FlexibilityNo 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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