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$104+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Gotogate deal was found by Cheapflights users on 10/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/145:30 amBOS - YWG
1 stop5h 46mAir Canada
Sun 12/217:05 pmYWG - BOS
2 stops18h 47mAir Canada
Deal found 10/30$533
This Gotogate deal was found by Cheapflights users on 10/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/143:40 pmBOS - YWG
2 stops8h 55mMultiple Airlines
Sun 12/217:05 pmYWG - BOS
2 stops18h 47mMultiple Airlines
Deal found 10/30$555
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/243:40 pmBOS - YWG
1 stop20h 33mMultiple Airlines
Tue 12/309:00 pmYWG - BOS
2 stops27h 14mMultiple Airlines
Deal found 10/29$556
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/2411:09 amBOS - YWG
2 stops14h 32mMultiple Airlines
Mon 12/2912:10 pmYWG - BOS
1 stop8h 55mMultiple Airlines
Deal found 10/29$581
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/243:40 pmBOS - YWG
1 stop20h 33mPorter Airlines
Tue 12/306:00 amYWG - BOS
1 stop26h 35mPorter Airlines
Deal found 10/29$594
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 12/2310:37 amBOS - YWG
1 stop29h 30mMultiple Airlines
Mon 12/2912:10 pmYWG - BOS
1 stop8h 55mMultiple Airlines
Deal found 10/29$611
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/243:40 pmBOS - YWG
1 stop20h 33mPorter Airlines
Mon 12/2912:10 pmYWG - BOS
1 stop8h 55mPorter Airlines
Deal found 10/29$615
This Air Canada deal was found by Cheapflights users on 10/29. 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.
Tue 12/235:30 amBOS - YWG
1 stop5h 46mAir Canada
Tue 12/305:30 amYWG - BOS
2 stops8h 22mAir Canada
Deal found 10/29$616
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:50 amBOS - YWG
2 stops16h 45mAmerican Airlines
Tue 12/306:00 amYWG - BOS
2 stops11h 03mAmerican Airlines
Deal found 10/29$640

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$259
(Kiwi.com)

One-way from

$187
(Kiwi.com)

Popular in

February

Cheapest in

July

Average price

$417
Provider with most accurate pricing for Boston Logan Intl-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Winnipeg flights.
Search Deals
From Massachusetts to Winnipeg
Search Deals
One-way flight from Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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 1/14

6:00 am-3:07 pm

1 stop10h 07m

Winnipeg

Wed 1/21

7:30 am-12:05 am

1 stop15h 35m

$259

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 2/24

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

Thu 2/26

8:15 am-2:52 pm

1 stop5h 37m

$454

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 12/14

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

Sun 12/21

7:05 pm-2:52 pm

2 stops18h 47m

$533

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 12/14

3:40 pm-11:35 pm

2 stops8h 55m

Winnipeg

Sun 12/21

7:05 pm-2:52 pm

2 stops18h 47m

$555

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 12/24

3:40 pm-11:13 am

1 stop20h 33m

Winnipeg

Tue 12/30

9:00 pm-1:14 am

2 stops27h 14m

$556

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 11/27

9:54 pm-3:07 pm

1 stop18h 13m

$104

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 11/4

6:00 am-3:07 pm

3 stops34h 07m

$187

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 12/14

6:00 am-11:57 am

1 stop6h 57m

$257

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 12/14

5:29 am-4:55 pm

2 stops12h 26m

$262

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 11/27

6:15 am-12:39 pm

1 stop7h 24m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 12 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, July is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of $128). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of $432). 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 October 30, 2025.

One of the essential ways to save on airfare from Massachusetts to Winnipeg is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 26% on airfare.

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?

    Air Canada can get you from Massachusetts to Winnipeg in just under 5h 46m. 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, July is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of $128). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of $432). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$134Average$488FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$172Average$569FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$426FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$335Average$438FlexibilityNo cancel feeOn-time52%

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