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$139+ 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
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 December 16, 2025.

This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/223:15 pmBOS - YWG
1 stop26h 40mWestJet
Mon 1/58:05 pmYWG - BOS
2 stops17h 12mWestJet
Deal found 12/15$841
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Tue 12/168:11 pmBOS - YWG
2 stops24h 24mMultiple Airlines
Tue 12/238:00 amYWG - BOS
1 stop25h 01mMultiple Airlines
Deal found 12/15$877
This FlightHub deal was found by Cheapflights users on 12/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:45 amBOS - YWG
1 stop7h 00mWestJet
Tue 12/308:05 pmYWG - BOS
2 stops20h 00mWestJet
Deal found 12/16$933
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:01 amBOS - YWG
1 stop6h 56mUnited Airlines
Mon 1/52:20 pmYWG - BOS
1 stop9h 25mUnited Airlines
Deal found 12/15$937
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:15 amBOS - YWG
1 stop14h 36mUnited Airlines
Tue 12/302:20 pmYWG - BOS
1 stop9h 25mUnited Airlines
Deal found 12/15$970
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1612:10 pmBOS - YWG
2 stops12h 34mDelta
Tue 12/236:40 amYWG - BOS
2 stops12h 34mDelta
Deal found 12/15$1,046
This FlightHub deal was found by Cheapflights users on 12/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:24 pmBOS - YWG
1 stop23h 31mWestJet
Wed 12/318:05 pmYWG - BOS
2 stops22h 42mWestJet
Deal found 12/16$1,063

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 December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(Kiwi.com)

One-way from

$139
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$642
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. 16% potential increase in price ($89 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 16, 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

5:34 am-12:41 am

3 stops20h 07m

Winnipeg

Tue 1/20

9:00 pm-4:19 pm

3 stops18h 19m

$323

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 1/16

3:43 pm-1:26 am

1 stop10h 43m

Winnipeg

Sun 1/18

7:30 am-1:13 am

1 stop16h 43m

$339

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 1/5

5:30 am-9:44 pm

2 stops17h 14m

Winnipeg

Tue 1/13

6:00 am-2:52 pm

2 stops7h 52m

$364

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 1/20

6:00 am-12:41 am

2 stops19h 41m

Winnipeg

Sat 1/24

4:25 pm-6:10 pm

1 stop24h 45m

$500

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 1/5

6:15 am-10:08 am

2 stops28h 53m

Winnipeg

Tue 1/13

4:10 pm-10:02 am

3 stops16h 52m

$552

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 1/20

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

Sat 1/24

8:15 am-2:52 pm

1 stop5h 37m

$560

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 1/14

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

Sat 1/17

8:15 am-2:52 pm

1 stop5h 37m

$560

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 3/8

12:35 pm-10:40 pm

3 stops35h 05m

$139

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 3/8

6:00 am-11:57 am

1 stop6h 57m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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 $449). 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 December 16, 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 17h 14m. 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 $449). 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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Alternative routes for Massachusetts to Winnipeg

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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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$134Average$477FlexibilityNo cancel feeOn-time67%
DeltaCheapest$143Average$420FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$172Average$569FlexibilityNo cancel feeOn-time69%

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