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$171+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Apr 17 — Apr 241
Fri 4/17
Fri 4/24
1 adult, Economy
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Cheap 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 March 18, 2026.

This Mytrip deal was found by Cheapflights users on 3/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:10 am
BOS
-
YWG
1 stop5h 53m
Air Canada
Sun 5/178:00 am
YWG
-
BOS
1 stop5h 47m
Air Canada
Deal found 3/14$325
This Mytrip deal was found by Cheapflights users on 3/18. 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.
Sat 5/210:35 am
BOS
-
YWG
1 stop5h 39m
Air Canada
Sat 5/95:10 am
YWG
-
BOS
1 stop5h 36m
Air Canada
Deal found 3/18$341
This Air Canada deal was found by Cheapflights users on 3/13. 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 5/235:10 am
BOS
-
YWG
1 stop6h 58m
Air Canada
Sat 5/308:00 am
YWG
-
BOS
1 stop5h 47m
Air Canada
Deal found 3/13$372
This FlightHub deal was found by Cheapflights users on 3/14. 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 5/147:10 am
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Tue 5/199:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 3/14$385
This Trip.com deal was found by Cheapflights users on 3/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:30 pm
BOS
-
YWG
1 stop17h 40m
WestJet
Mon 5/47:00 am
YWG
-
BOS
1 stop9h 40m
WestJet
Deal found 3/13$393
This Air Canada deal was found by Cheapflights users on 3/16. 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.
Wed 5/135:10 am
BOS
-
YWG
1 stop5h 53m
Air Canada
Sun 5/178:00 am
YWG
-
BOS
1 stop5h 47m
Air Canada
Deal found 3/16$394
This United Airlines deal was found by Cheapflights users on 3/17. 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.
Fri 5/18:25 pm
BOS
-
YWG
1 stop16h 27m
United Airlines
Fri 5/82:00 pm
YWG
-
BOS
1 stop9h 59m
United Airlines
Deal found 3/17$396
This Air Canada deal was found by Cheapflights users on 3/17. 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.
Sun 5/315:10 am
BOS
-
YWG
1 stop5h 53m
Air Canada
Thu 6/48:10 am
YWG
-
BOS
1 stop6h 58m
Air Canada
Deal found 3/17$398

Find flight deals from Massachusetts to Winnipeg

Keep the following information in mind while searching for Massachusetts to Winnipeg flight deals. Data was last updated March 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$325
(Mytrip)

One-way from

$171
(United Airlines)

Popular in

January

Cheapest in

May

Average price

$591
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.
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From Massachusetts to Winnipeg
Search Deals
One-way flight from Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($171 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in March 2026
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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 March 18, 2026.
Use the filters below to find and compare flights from Massachusetts to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 5/8

5:10 am-10:03 am

1 stop5h 53m

Winnipeg

Sun 5/17

8:00 am-2:47 pm

1 stop5h 47m

$325
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 5/2

10:35 am-3:14 pm

1 stop5h 39m

Winnipeg

Sat 5/9

5:10 am-11:46 am

1 stop5h 36m

$341

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 5/23

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Sat 5/30

9:20 am-8:55 pm

2 stops10h 35m

$381

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 4/27

6:30 pm-11:10 am

1 stop17h 40m

Winnipeg

Mon 5/4

7:00 am-5:40 pm

1 stop9h 40m

$393

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 4/30

5:30 am-10:09 am

1 stop5h 39m

Winnipeg

Thu 5/7

5:10 am-11:46 am

1 stop5h 36m

$394

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/13

5:10 am-10:03 am

1 stop5h 53m

Winnipeg

Sun 5/17

8:00 am-2:47 pm

1 stop5h 47m

$394

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 5/1

8:25 pm-11:52 am

1 stop16h 27m

Winnipeg

Fri 5/8

2:00 pm-12:59 am

1 stop9h 59m

$396
Cheapest one-way

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 5/1

8:25 pm-11:52 am

1 stop16h 27m

$171
Quickest one-way

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 4/28

5:50 am-10:56 am

1 stop6h 06m

$171

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 4/28

12:52 pm-8:15 pm

3 stops32h 23m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/17

Showing 1-10 of 12 resultsSorted by cheapest first
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, May is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of $118). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of $438). 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.

How much does it cost to fly round-trip from Massachusetts to Winnipeg?

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 and Porter Airlines can get you from Massachusetts to Winnipeg in just under 5h 53m. Your travel time can differ by up to 21m. Airlines will cover a distance of 1350 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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, May is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of $118). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of $438). 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 3 airlines flying from Massachusetts to Winnipeg

Discover the top 3 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 March 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$131Average$420FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$187Average$611FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$194Average$494FlexibilityNo cancel feeOn-time67%

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