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$138+ Cheap flights from Massachusetts to Winnipeg (YWG)

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 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Jun 20 — Jun 271
Fri 6/20
Fri 6/27
1 adult, Economy
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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 June 15, 2025.

Round-trip from

$300
(Air Canada)

One-way from

$138
(Delta)

Popular in

March

Cheapest in

January

Average price

$433
From Massachusetts to Winnipeg
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One-way flight from Massachusetts to Winnipeg
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Highest demand for flights based on searches. 18% potential increase in price ($106 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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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 June 15, 2025.

This Air Canada deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/245:50 amBOS - YWG
1 stop7h 14mAir Canada
Wed 8/65:00 amYWG - BOS
1 stop5h 28mAir Canada
Deal found 6/14$300
This United Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2111:00 amBOS - YWG
1 stop12h 33mUnited Airlines
Mon 8/254:25 pmYWG - BOS
1 stop12h 34mUnited Airlines
Deal found 6/13$308
This Mytrip deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:00 amBOS - YWG
2 stops35h 22mMultiple Airlines
Sat 9/279:15 pmYWG - BOS
1 stop19h 55mMultiple Airlines
Deal found 6/12$320
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/247:15 amBOS - YWG
1 stop10h 35mDelta
Wed 8/612:26 pmYWG - BOS
2 stops12h 13mDelta
Deal found 6/14$358
This FlightHub deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/312:15 pmBOS - YWG
2 stops11h 31mPorter Airlines
Sun 7/611:45 amYWG - BOS
2 stops8h 46mPorter Airlines
Deal found 6/14$690
This oojo deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/37:15 amBOS - YWG
2 stops15h 11mWestJet
Sun 7/66:30 pmYWG - BOS
2 stops26h 58mWestJet
Deal found 6/13$907

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 2,558,603 searches. Data last updated June 15, 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

Thu 7/24

5:50 am-12:04 pm

1 stop7h 14m

Winnipeg

Wed 8/6

5:00 am-11:28 am

1 stop5h 28m

$300

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 8/21

11:00 am-10:33 pm

1 stop12h 33m

Winnipeg

Mon 8/25

4:25 pm-5:59 am

1 stop12h 34m

$308

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 7/24

7:15 am-4:50 pm

1 stop10h 35m

Winnipeg

Wed 8/6

12:26 pm-1:39 am

2 stops12h 13m

$358

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 7/9

6:10 am-12:31 am

3 stops19h 21m

Winnipeg

Mon 7/14

11:45 am-6:28 pm

1 stop5h 43m

$367

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 7/3

12:15 pm-10:46 pm

2 stops11h 31m

Winnipeg

Sun 7/6

11:45 am-9:31 pm

2 stops8h 46m

$690

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 7/3

7:15 am-9:26 pm

2 stops15h 11m

Winnipeg

Sun 7/6

6:30 pm-10:28 pm

2 stops26h 58m

$907

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 6/25

8:15 am-4:52 pm

1 stop9h 37m

$138

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 7/28

8:48 pm-12:31 am

3 stops28h 43m

$156

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 7/6

7:00 am-9:08 pm

2 stops15h 08m

$227

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 7/6

5:50 am-5:40 pm

2 stops12h 50m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

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, August is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of $358). Flying from Massachusetts to Winnipeg in December is currently the most expensive (average of $497). 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 MA to YWG?

Find hourly flight availability from Massachusetts to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 15, 2025.

When flying from Massachusetts to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

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 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

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 June 15, 2025.
Read through reviews of airlines operating flights from Massachusetts to Winnipeg, such as Porter Airlines, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
289 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Overall

8.0

Food

7.6

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
289 reviews
Porter Airlines
8.0
Very good
289 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Overall

8.0

Food

7.6

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
7,961 reviews
Porter Airlines
8.0
Very good
289 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Overall

8.0

Food

7.6

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
8,798 reviews
Porter Airlines
8.0
Very good
289 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Overall

8.0

Food

7.6

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
2,872 reviews
Porter Airlines
8.0
Very good
289 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Overall

8.0

Food

7.6

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
9,549 reviews
Porter Airlines
8.0
Very good
289 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Overall

8.0

Food

7.6

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?

    Winnipeg (YWG), located 4.6 mi from the city center, is the airport you fly into when you book flights from Massachusetts to Winnipeg.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $138. However, be on the lookout for offers from Air Canada and United Airlines, as they are both options that can get you from Massachusetts to Winnipeg for a low price.

  • 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, August is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of $358). Flying from Massachusetts to Winnipeg in December is currently the most expensive (average of $497). 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 Massachusetts to Winnipeg

Discover the top 4 airlines that operate flights from Massachusetts to Winnipeg. 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 2,558,603 searches. Data last updated June 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$134Average$457FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$172Average$569FlexibilityNo cancel feeOn-time69%
DeltaCheapest$274Average$458FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$283Average$438FlexibilityNo cancel feeOn-time52%

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