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$119+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$263
(Kiwi.com)

One-way from

$119
(Air Canada)

Popular in

February

Cheapest in

July

Average price

$526
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. 5% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:30 pmBOS - YWG
1 stop18h 11mMultiple Airlines
Fri 10/317:30 amYWG - BOS
1 stop26h 18mMultiple Airlines
Deal found 9/13$263
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:24 pmBOS - YWG
2 stops20h 58mMultiple Airlines
Mon 10/206:30 amYWG - BOS
1 stop10h 10mMultiple Airlines
Deal found 9/15$280
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:00 pmBOS - YWG
2 stops29h 40mMultiple Airlines
Thu 10/27:00 pmYWG - BOS
1 stop21h 40mMultiple Airlines
Deal found 9/15$331
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2312:49 pmBOS - YWG
2 stops12h 24mMultiple Airlines
Fri 10/314:00 pmYWG - BOS
1 stop15h 28mMultiple Airlines
Deal found 9/13$342
This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:45 pmBOS - YWG
1 stop7h 09mAir Canada
Sat 11/18:15 amYWG - BOS
1 stop5h 37mAir Canada
Deal found 9/13$344
This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:00 amBOS - YWG
2 stops11h 15mAir Canada
Fri 10/311:45 pmYWG - BOS
1 stop6h 42mAir Canada
Deal found 9/13$349
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/2311:02 amBOS - YWG
1 stop12h 31mUnited Airlines
Wed 10/292:20 pmYWG - BOS
1 stop6h 29mUnited Airlines
Deal found 9/13$352
This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:00 amBOS - YWG
2 stops12h 45mAir Canada
Wed 10/296:00 amYWG - BOS
2 stops7h 52mAir Canada
Deal found 9/13$354
This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:45 pmBOS - YWG
1 stop7h 09mAir Canada
Mon 11/35:30 amYWG - BOS
2 stops12h 42mAir Canada
Deal found 9/13$356
This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:00 amBOS - YWG
2 stops12h 45mAir Canada
Mon 11/35:30 amYWG - BOS
2 stops12h 42mAir Canada
Deal found 9/13$361

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 September 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 10/16

8:24 pm-4:22 pm

2 stops20h 58m

Winnipeg

Mon 10/20

6:30 am-5:40 pm

1 stop10h 10m

$280

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 9/26

7:00 pm-11:40 pm

2 stops29h 40m

Winnipeg

Thu 10/2

7:00 pm-5:40 pm

1 stop21h 40m

$331

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 10/25

6:00 am-3:31 pm

1 stop10h 31m

Winnipeg

Mon 11/3

8:40 am-11:39 pm

1 stop13h 59m

$352

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/23

8:00 am-10:33 pm

1 stop15h 33m

Winnipeg

Sat 11/1

2:20 pm-9:49 pm

1 stop6h 29m

$352

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 10/20

7:15 pm-9:41 am

1 stop15h 26m

Winnipeg

Tue 10/28

12:20 pm-10:05 pm

1 stop8h 45m

$352

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/23

11:02 am-10:33 pm

1 stop12h 31m

Winnipeg

Wed 10/29

2:20 pm-9:49 pm

1 stop6h 29m

$352

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 10/24

6:00 am-5:45 pm

2 stops12h 45m

Winnipeg

Sat 11/1

6:00 am-2:52 pm

2 stops7h 52m

$354

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 10/24

6:00 am-5:45 pm

2 stops12h 45m

Winnipeg

Tue 10/28

6:00 am-2:52 pm

2 stops7h 52m

$354

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 10/24

6:00 am-5:45 pm

2 stops12h 45m

Winnipeg

Mon 11/3

5:30 am-7:12 pm

2 stops12h 42m

$361

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/23

6:00 am-10:33 pm

1 stop17h 33m

Winnipeg

Tue 10/28

8:40 am-10:47 pm

2 stops13h 07m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 17 results
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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 $501). 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 September 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.

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.

  • How long is the flight from Massachusetts to Winnipeg?

    United Airlines can get you from Massachusetts to Winnipeg in just under 10h 31m. Your travel time can differ by up to . Airlines will cover a distance of 1350 mi.

  • 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 $501). 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

Traveling to a place near Winnipeg?

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

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$134Average$425FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$172Average$559FlexibilityNo cancel feeOn-time69%
DeltaCheapest$274Average$424FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$283Average$438FlexibilityNo cancel feeOn-time52%

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