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Cheap flights from Massachusetts to Winnipeg from C$ 176

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 25/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
5 Apr — 12 Apr1
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 31 March 2025.

Round-trip from

C$ 416

One-way from

C$ 176

Popular in

April

Cheapest in

January

Average price

C$ 920
Air Canada
  • Air Canada
  • 12/5-19/5
  • 2 total stops
  • 11h 34m total
  • Massachusetts to Winnipeg
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Delta
  • Delta
  • 25/5
  • 1 total stop
  • 9h 53m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 19% potential increase in price (C$ 259 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 47 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 31 March 2025.

Mon 12/57:00 p.m.BOS - YWG
1 stop6h 02mAir Canada
Mon 19/58:00 a.m.YWG - BOS
1 stop5h 32mAir Canada
Deal found 30/3C$ 416
Thu 1/58:25 p.m.BOS - YWG
1 stop17h 44mUnited Airlines
Wed 7/55:00 a.m.YWG - BOS
1 stop5h 28mUnited Airlines
Deal found 31/3C$ 424
Tue 29/43:50 p.m.BOS - YWG
1 stop25h 38mMultiple Airlines
Tue 6/56:30 a.m.YWG - BOS
2 stops32h 54mMultiple Airlines
Deal found 30/3C$ 431
Thu 1/53:30 p.m.BOS - YWG
1 stop8h 58mDelta
Wed 7/512:52 p.m.YWG - BOS
2 stops9h 54mDelta
Deal found 31/3C$ 442
Sat 18/104:56 p.m.BDL - YWG
2 stops28h 50mMultiple Airlines
Sat 25/103:00 p.m.YWG - BDL
3 stops16h 10mMultiple Airlines
Deal found 30/3C$ 774
Wed 2/77:36 p.m.ALB - YWG
2 stops21h 37mUnited Airlines
Tue 15/72:50 p.m.YWG - ALB
2 stops18h 33mUnited Airlines
Deal found 31/3C$ 814
Thu 15/57:24 p.m.ALB - YWG
3 stops29h 49mMultiple Airlines
Thu 22/511:25 a.m.YWG - ALB
3 stops29h 41mMultiple Airlines
Deal found 31/3C$ 830
Fri 29/87:00 a.m.BDL - YWG
1 stop10h 23mDelta
Mon 1/99:00 a.m.YWG - BDL
1 stop10h 18mDelta
Deal found 30/3C$ 1,019
Wed 2/76:00 a.m.ALB - YWG
2 stops18h 11mWestJet
Tue 15/79:00 a.m.YWG - ALB
1 stop13h 39mWestJet
Deal found 31/3C$ 1,075
Fri 29/811:16 a.m.BDL - YWG
2 stops12h 55mWestJet
Mon 1/95:38 p.m.YWG - BDL
1 stop5h 14mWestJet
Deal found 30/3C$ 1,102
Wed 2/71:10 p.m.ALB - YWG
1 stop10h 23mAir Canada
Tue 15/77:00 a.m.YWG - ALB
1 stop7h 09mAir Canada
Deal found 31/3C$ 1,134
Thu 15/56:00 a.m.ALB - YWG
1 stop11h 28mDelta
Thu 22/59:00 a.m.YWG - ALB
1 stop8h 00mDelta
Deal found 31/3C$ 1,144

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 31 March 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

Mon 12/5

7:00 p.m.-12:02 a.m.

1 stop6h 02m

Winnipeg

Mon 19/5

8:00 a.m.-2:32 p.m.

1 stop5h 32m

C$ 416

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/5

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

1 stop17h 44m

Winnipeg

Wed 7/5

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

1 stop5h 28m

C$ 424

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 29/4

3:50 p.m.-4:28 p.m.

1 stop25h 38m

Winnipeg

Tue 6/5

6:30 a.m.-4:24 p.m.

2 stops32h 54m

C$ 431

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/5

3:30 p.m.-11:28 p.m.

1 stop8h 58m

Winnipeg

Wed 7/5

12:52 p.m.-11:46 p.m.

2 stops9h 54m

C$ 442

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Wed 2/7

7:36 p.m.-4:13 p.m.

2 stops21h 37m

Winnipeg

Tue 15/7

2:50 p.m.-10:23 a.m.

2 stops18h 33m

C$ 814

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Thu 15/5

7:24 p.m.-12:13 a.m.

3 stops29h 49m

Winnipeg

Thu 22/5

11:25 a.m.-6:06 p.m.

3 stops29h 41m

C$ 830

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Fri 29/8

7:00 a.m.-4:23 p.m.

1 stop10h 23m

Winnipeg

Mon 1/9

9:00 a.m.-8:18 p.m.

1 stop10h 18m

C$ 1,019

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Wed 2/7

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

2 stops18h 11m

Winnipeg

Tue 15/7

9:00 a.m.-11:39 p.m.

1 stop13h 39m

C$ 1,075

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Fri 29/8

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

2 stops12h 55m

Winnipeg

Mon 1/9

5:38 p.m.-11:52 p.m.

1 stop5h 14m

C$ 1,102

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Wed 2/7

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

1 stop10h 23m

Winnipeg

Tue 15/7

7:00 a.m.-3:09 p.m.

1 stop7h 09m

C$ 1,134

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/3

Showing 1-10 of 16 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 31 March 2025.
To help decide which airline to fly from Massachusetts to Winnipeg, see what other customers have to say about Delta, United Airlines and WestJet. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,899 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,614 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,789 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.0
Good
9,012 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 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
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?

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

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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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