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Cheap flights from Massachusetts to Winnipeg from C$ 148

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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 373

One-way from

C$ 148

Popular in

March

Cheapest in

January

Average price

C$ 592
WestJet
  • WestJet
  • 3/10-19/10
  • 2 total stops
  • 28h 21m total
  • Massachusetts to Winnipeg
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WestJet
  • WestJet
  • 5/10
  • 1 total stop
  • 15h 31m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 197 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 12 June 2025.

Fri 3/106:30 p.m.BOS - YWG
1 stop18h 11mWestJet
Sun 19/106:30 a.m.YWG - BOS
1 stop10h 10mWestJet
Deal found 11/6C$ 373
Thu 24/75:50 a.m.BOS - YWG
1 stop7h 14mAir Canada
Wed 6/85:00 a.m.YWG - BOS
1 stop5h 28mAir Canada
Deal found 11/6C$ 410
Thu 21/87:45 a.m.BOS - YWG
1 stop15h 48mUnited Airlines
Mon 25/84:25 p.m.YWG - BOS
1 stop12h 34mUnited Airlines
Deal found 10/6C$ 420
Thu 24/77:15 a.m.BOS - YWG
1 stop10h 35mDelta
Wed 6/86:45 a.m.YWG - BOS
2 stops12h 28mDelta
Deal found 11/6C$ 462
Fri 1/89:32 a.m.BOS - YWG
1 stop7h 23mMultiple Airlines
Tue 5/89:05 p.m.YWG - BOS
2 stops20h 05mMultiple Airlines
Deal found 12/6C$ 489
Sat 26/76:00 a.m.BDL - YWG
1 stop13h 39mMultiple Airlines
Sat 2/89:10 a.m.YWG - BDL
1 stop14h 15mMultiple Airlines
Deal found 11/6C$ 533
Wed 20/83:30 p.m.BOS - YWG
1 stop8h 16mPorter Airlines
Sun 24/811:45 a.m.YWG - BOS
1 stop5h 13mPorter Airlines
Deal found 12/6C$ 682
Tue 8/76:57 p.m.BDL - YWG
1 stop5h 28mDelta
Tue 15/75:42 p.m.YWG - BDL
1 stop5h 09mDelta
Deal found 11/6C$ 1,032
Tue 8/71:03 p.m.BDL - YWG
1 stop10h 30mUnited Airlines
Tue 15/77:00 a.m.YWG - BDL
2 stops15h 59mUnited Airlines
Deal found 10/6C$ 1,045
Fri 25/76:15 a.m.BDL - YWG
1 stop11h 35mWestJet
Fri 1/85:42 p.m.YWG - BDL
1 stop5h 09mWestJet
Deal found 10/6C$ 1,622

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 12 June 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

Fri 3/10

6:30 p.m.-11:41 a.m.

1 stop18h 11m

Winnipeg

Sun 19/10

6:30 a.m.-5:40 p.m.

1 stop10h 10m

C$ 373

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 24/7

5:50 a.m.-12:04 p.m.

1 stop7h 14m

Winnipeg

Wed 6/8

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

1 stop5h 28m

C$ 410

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 21/8

7:45 a.m.-10:33 p.m.

1 stop15h 48m

Winnipeg

Mon 25/8

4:25 p.m.-5:59 a.m.

1 stop12h 34m

C$ 420

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 4/7

1:10 p.m.-11:29 p.m.

2 stops11h 19m

Winnipeg

Thu 21/8

8:35 a.m.-7:25 p.m.

1 stop9h 50m

C$ 448

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 1/8

9:32 a.m.-3:55 p.m.

1 stop7h 23m

Winnipeg

Tue 5/8

9:05 p.m.-6:10 p.m.

2 stops20h 05m

C$ 489

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Sat 26/7

6:00 a.m.-6:39 p.m.

1 stop13h 39m

Winnipeg

Sat 2/8

9:10 a.m.-12:25 a.m.

1 stop14h 15m

C$ 533

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 20/8

3:30 p.m.-10:46 p.m.

1 stop8h 16m

Winnipeg

Sun 24/8

11:45 a.m.-5:58 p.m.

1 stop5h 13m

C$ 682

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Tue 8/7

6:57 p.m.-11:25 p.m.

1 stop5h 28m

Winnipeg

Tue 15/7

5:42 p.m.-11:51 p.m.

1 stop5h 09m

C$ 1,032

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Tue 8/7

1:03 p.m.-10:33 p.m.

1 stop10h 30m

Winnipeg

Tue 15/7

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

2 stops15h 59m

C$ 1,045

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Fri 25/7

6:15 a.m.-4:50 p.m.

1 stop11h 35m

Winnipeg

Fri 1/8

5:42 p.m.-11:51 p.m.

1 stop5h 09m

C$ 1,622

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 19 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$ 123). Flying from Massachusetts to Winnipeg in July is currently the most expensive (average of C$ 229). 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 12 June 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
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,950 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,790 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Canada
7.1
Good
9,531 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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 WestJet. According to our data, you can fly for as low as C$ 148. Users have also found prices from C$ 174 and C$ 183 on United Airlines and Air Canada, 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$ 123). Flying from Massachusetts to Winnipeg in July is currently the most expensive (average of C$ 229). 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

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 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?

Of course! You can now track prices for flights from Massachusetts to Winnipeg and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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