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Cheap flights from Massachusetts to Winnipeg from C$ 140

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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
30 Apr — 7 May1
1 adult

Cheap flight deals from Massachusetts to Winnipeg

Keep the following information in mind while searching for Massachusetts to Winnipeg flight deals. Data was last updated 25 April 2025.

Round-trip from

C$ 366

One-way from

C$ 140

Popular in

April

Cheapest in

January

Average price

C$ 1,067
United Airlines
  • United Airlines
  • 11/6-14/6
  • 3 total stops
  • 18h 25m total
  • Massachusetts to Winnipeg
Search Deals
United Airlines
  • United Airlines
  • 9/5
  • 1 total stop
  • 17h 44m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 290 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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Find flight deals from Massachusetts to Winnipeg

Cheapest flights from Massachusetts to Winnipeg
Explore the most affordable flight options available from Massachusetts to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 25 April 2025.

Wed 11/66:00 a.m.BOS - YWG
2 stops13h 02mUnited Airlines
Sat 14/65:00 a.m.YWG - BOS
1 stop5h 23mUnited Airlines
Deal found 24/4C$ 366
Wed 11/611:16 a.m.BOS - YWG
1 stop9h 56mDelta
Fri 13/612:26 p.m.YWG - BOS
1 stop8h 54mDelta
Deal found 23/4C$ 381
Mon 9/610:20 a.m.BOS - YWG
2 stops8h 42mAir Canada
Sun 15/65:00 a.m.YWG - BOS
1 stop5h 28mAir Canada
Deal found 25/4C$ 543
Fri 23/55:42 p.m.BOS - YWG
1 stop25h 57mMultiple Airlines
Mon 26/511:25 a.m.YWG - BOS
1 stop5h 43mMultiple Airlines
Deal found 24/4C$ 553
Sat 8/114:15 p.m.BOS - YWG
1 stop5h 54mPorter Airlines
Sat 15/1111:35 a.m.YWG - BOS
1 stop5h 40mPorter Airlines
Deal found 25/4C$ 579
Fri 9/57:52 p.m.BDL - YWG
2 stops20h 39mUnited Airlines
Sun 11/55:00 a.m.YWG - BDL
2 stops17h 59mUnited Airlines
Deal found 24/4C$ 801
Mon 28/45:45 a.m.BDL - YWG
2 stops35h 40mMultiple Airlines
Wed 7/511:25 a.m.YWG - BDL
3 stops29h 28mMultiple Airlines
Deal found 23/4C$ 902
Fri 5/96:00 a.m.ALB - YWG
1 stop11h 22mDelta
Thu 11/99:00 a.m.YWG - ALB
2 stops13h 08mDelta
Deal found 25/4C$ 914
Fri 9/57:05 a.m.BDL - YWG
1 stop10h 23mDelta
Sun 11/56:30 a.m.YWG - BDL
2 stops12h 48mDelta
Deal found 24/4C$ 1,188
Thu 1/56:23 p.m.ALB - YWG
3 stops45h 28mMultiple Airlines
Sun 4/55:10 p.m.YWG - ALB
2 stops29h 11mMultiple Airlines
Deal found 23/4C$ 1,212
Thu 1/56:00 a.m.ALB - YWG
1 stop10h 31mUnited Airlines
Sun 4/52:20 p.m.YWG - ALB
2 stops18h 45mUnited Airlines
Deal found 23/4C$ 1,237
Fri 9/56:54 p.m.BDL - YWG
1 stop5h 31mWestJet
Sun 11/55:35 p.m.YWG - BDL
1 stop4h 58mWestJet
Deal found 24/4C$ 1,377

Cheapflights Fare Finder

Customize your flight search to find flights from Massachusetts to Winnipeg 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 25 April 2025.
Use the filters below to find and compare flights from Massachusetts to Winnipeg that are best for you.

Fly from

Massachusetts

Fly to

Winnipeg

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 11/6

6:00 a.m.-6:02 p.m.

2 stops13h 02m

Winnipeg

Sat 14/6

5:00 a.m.-11:23 a.m.

1 stop5h 23m

C$ 366

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 11/6

11:16 a.m.-8:12 p.m.

1 stop9h 56m

Winnipeg

Fri 13/6

12:26 p.m.-10:20 p.m.

1 stop8h 54m

C$ 381

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 9/6

10:20 a.m.-6:02 p.m.

2 stops8h 42m

Winnipeg

Sun 15/6

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

1 stop5h 28m

C$ 543

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 23/5

5:42 p.m.-6:39 p.m.

1 stop25h 57m

Winnipeg

Mon 26/5

11:25 a.m.-6:08 p.m.

1 stop5h 43m

C$ 553

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 9/6

12:15 p.m.-10:46 p.m.

2 stops11h 31m

Winnipeg

Sun 15/6

11:45 a.m.-9:31 p.m.

2 stops8h 46m

C$ 607

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Fri 9/5

7:52 p.m.-3:31 p.m.

2 stops20h 39m

Winnipeg

Sun 11/5

5:00 a.m.-11:59 p.m.

2 stops17h 59m

C$ 801

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Fri 5/9

6:00 a.m.-4:22 p.m.

1 stop11h 22m

Winnipeg

Thu 11/9

9:00 a.m.-11:08 p.m.

2 stops13h 08m

C$ 914

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Fri 9/5

7:05 a.m.-4:28 p.m.

1 stop10h 23m

Winnipeg

Sun 11/5

6:30 a.m.-8:18 p.m.

2 stops12h 48m

C$ 1,188

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Fri 9/5

6:54 p.m.-11:25 p.m.

1 stop5h 31m

Winnipeg

Sun 11/5

5:35 p.m.-11:33 p.m.

1 stop4h 58m

C$ 1,377

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 9/5

8:25 p.m.-1:09 p.m.

1 stop17h 44m

C$ 140

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/4

Showing 1-10 of 18 results
1
2

Best time to book a flight from Massachusetts to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Massachusetts 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 Massachusetts to Winnipeg

What is the cheapest month to book a flight from Massachusetts to Winnipeg?

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 124). Flying from Massachusetts to Winnipeg in July is currently the most expensive (average of C$ 232). 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.

Rainfall in Winnipeg by month

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

In terms of precipitation, rainfall in Winnipeg ranges from 20.0 - 80.0 mm per month. June is typically the wettest month, when rainfall can reach 80.0 mm. January is typically the driest time to visit Winnipeg when rainfall is around 20.0 mm.

Temperature in Winnipeg by month

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

If weather is an important factor for your trip to Winnipeg, 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 20.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -16.0 C).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated 25 April 2025.
To help decide which airline to fly from Massachusetts to Winnipeg, see what other customers have to say about Porter Airlines, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
285 reviews
Check prices

Comfort

8.1

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.8

Food

7.6

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

Comfort

8.1

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.8

Food

7.6

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
7,920 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Comfort

8.1

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.8

Food

7.6

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
8,685 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Comfort

8.1

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.8

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,816 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Comfort

8.1

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.8

Food

7.6

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
9,197 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Comfort

8.1

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.8

Food

7.6

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 Massachusetts to Winnipeg. 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 into for flights to Winnipeg from Massachusetts?

    If you book a flight to Winnipeg from Massachusetts, you will be flying to Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg.

  • What are the cheapest airlines to fly from Massachusetts to Winnipeg one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as C$ 140. Users have also found prices from C$ 152 and C$ 270 on Delta and Porter Airlines, respectively.

  • What are the most popular routes from Massachusetts to Winnipeg?

    Most travellers choose Boston Logan Intl - Winnipeg, Hartford Bradley Intl - Winnipeg or Albany Intl - Winnipeg when deciding on the best route from Massachusetts to Winnipeg.

  • Can I find deals for flights from Massachusetts to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Winnipeg.

  • Can I find deals for business class flights from Massachusetts to Winnipeg?

    Yes. Cheapflights offers flight deals from Massachusetts to Winnipeg 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 Massachusetts to Winnipeg?

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 124). Flying from Massachusetts to Winnipeg in July is currently the most expensive (average of C$ 232). 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

Travelling to a place near Massachusetts?

Book flights to Massachusetts if you plan to visit one of these locations
Selkirk
Portage la Prairie

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Fly with Cheapflights

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

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Massachusetts to Winnipeg. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

Cheapflights simply makes it quick and affordable to book flights from Massachusetts to Winnipeg by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Massachusetts to Winnipeg with no change fees?

Need flexible booking options for your flight to Winnipeg from Massachusetts? 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 Massachusetts to Winnipeg become cheaper?

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