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Cheap flights from Winnipeg to Massachusetts from C$ 216

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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
4 May — 11 May1
1 adult

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 29 April 2025.

Round-trip from

C$ 388

One-way from

C$ 216

Popular in

December

Cheapest in

October

Average price

C$ 491
Delta
  • Delta
  • 10/7-6/8
  • 2 total stops
  • 15h 54m total
  • Winnipeg to Massachusetts
Search Deals
United Airlines
  • United Airlines
  • 12/6
  • 1 total stop
  • 9h 39m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 20% potential increase in price (C$ 207 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

Find flight deals from Winnipeg to Massachusetts

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 29 April 2025.

Thu 10/712:26 p.m.YWG - BOS
2 stops10h 27mDelta
Wed 6/85:35 a.m.BOS - YWG
1 stop6h 56mDelta
Deal found 28/4C$ 388
Wed 21/52:20 p.m.YWG - BOS
2 stops8h 39mUnited Airlines
Tue 27/56:00 a.m.BOS - YWG
1 stop10h 31mUnited Airlines
Deal found 28/4C$ 399
Fri 25/711:45 a.m.YWG - BOS
2 stops9h 16mPorter Airlines
Fri 1/83:50 p.m.BOS - YWG
1 stop7h 56mPorter Airlines
Deal found 28/4C$ 492
Wed 6/85:00 a.m.YWG - BOS
1 stop5h 28mAir Canada
Sun 10/85:50 a.m.BOS - YWG
1 stop5h 29mAir Canada
Deal found 28/4C$ 525
Sat 7/611:45 a.m.YWG - BOS
2 stops20h 24mMultiple Airlines
Wed 11/63:50 p.m.BOS - YWG
1 stop7h 56mMultiple Airlines
Deal found 28/4C$ 534

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 29 April 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

Thu 10/7

12:26 p.m.-11:53 p.m.

2 stops10h 27m

Boston Logan Intl

Wed 6/8

5:35 a.m.-11:31 a.m.

1 stop6h 56m

C$ 388

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 21/5

2:20 p.m.-11:59 p.m.

2 stops8h 39m

Boston Logan Intl

Tue 27/5

6:00 a.m.-3:31 p.m.

1 stop10h 31m

C$ 399

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 25/7

11:45 a.m.-10:01 p.m.

2 stops9h 16m

Boston Logan Intl

Fri 1/8

3:50 p.m.-10:46 p.m.

1 stop7h 56m

C$ 492

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 6/8

5:00 a.m.-11:28 a.m.

1 stop5h 28m

Boston Logan Intl

Sun 10/8

5:50 a.m.-10:19 a.m.

1 stop5h 29m

C$ 525

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 7/6

11:45 a.m.-9:09 a.m.

2 stops20h 24m

Boston Logan Intl

Wed 11/6

3:50 p.m.-10:46 p.m.

1 stop7h 56m

C$ 534

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 12/6

2:20 p.m.-12:59 a.m.

1 stop9h 39m

C$ 216

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 11/9

9:00 a.m.-11:29 p.m.

2 stops13h 29m

C$ 281

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 6/5

8:35 a.m.-7:08 p.m.

1 stop9h 33m

C$ 805

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

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, January is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 298). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 350). 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 29 April 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Massachusetts as you normally would.

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 78.0 - 101.0 mm per month. March is typically the wettest month, when rainfall can reach 101.0 mm. July is typically the driest time to visit Massachusetts when rainfall is around 78.0 mm.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -1.0 C).

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 29 April 2025.
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,929 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,696 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,240 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Crew

8.8

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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.

  • 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, January is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 298). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 350). 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 29 April 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 309AverageC$ 380FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 329AverageC$ 522FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 345AverageC$ 543FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 368AverageC$ 500FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Winnipeg to Massachusetts?

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Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Massachusetts?

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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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