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$134+ 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
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 May 7, 2026.

This Trip.com deal was found by Cheapflights users on 5/3. 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.
Thu 9/1710:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Tue 9/299:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 5/3$285
This FlightHub deal was found by Cheapflights users on 5/3. 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 7/1610:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Tue 7/219:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 5/3$300
This Air Canada deal was found by Cheapflights users on 5/2. 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 9/96:00 am
BOS
-
YWG
1 stop6h 12m
Air Canada
Sat 9/128:10 am
YWG
-
BOS
1 stop5h 31m
Air Canada
Deal found 5/2$312
This Delta deal was found by Cheapflights users on 5/3. 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.
Sat 9/511:15 am
BOS
-
YWG
1 stop9h 54m
Delta
Sun 9/1312:40 pm
YWG
-
BOS
1 stop10h 12m
Delta
Deal found 5/3$315
This Air Canada deal was found by Cheapflights users on 5/2. 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 8/2310:40 am
BOS
-
YWG
1 stop5h 34m
Air Canada
Fri 8/283:20 pm
YWG
-
BOS
1 stop6h 18m
Air Canada
Deal found 5/2$320
This Delta deal was found by Cheapflights users on 5/3. 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 7/95:55 am
BOS
-
YWG
1 stop10h 12m
Delta
Wed 7/1512:46 pm
YWG
-
BOS
1 stop10h 09m
Delta
Deal found 5/3$323
This Gotogate deal was found by Cheapflights users on 5/6. 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.
Wed 7/810:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Wed 7/159:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 5/6$324
This Air Canada deal was found by Cheapflights users on 5/3. 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 9/56:00 am
BOS
-
YWG
1 stop6h 15m
Air Canada
Sun 9/135:10 am
YWG
-
BOS
2 stops8h 31m
Air Canada
Deal found 5/3$325
This Air Canada deal was found by Cheapflights users on 5/2. 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 7/95:45 am
BOS
-
YWG
2 stops11h 35m
Air Canada
Tue 7/145:00 am
YWG
-
BOS
1 stop5h 52m
Air Canada
Deal found 5/2$334
This Justfly.com deal was found by Cheapflights users on 5/6. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Thu 10/229:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 5/6$336

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 May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$285
(Trip.com)

One-way from

$134
(United Airlines)

Popular in

January

Cheapest in

May

Average price

$391
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. 22% potential increase in price ($153 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 7, 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

Sat 9/5

11:15 am-8:09 pm

1 stop9h 54m

Winnipeg

Sat 9/12

12:40 pm-10:20 pm

1 stop8h 40m

$315

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/9

12:30 pm-10:33 pm

1 stop11h 03m

Winnipeg

Sat 9/12

2:00 pm-1:05 am

1 stop10h 05m

$315

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 7/10

2:52 pm-11:29 pm

1 stop9h 37m

Winnipeg

Wed 7/15

12:46 pm-11:55 pm

1 stop10h 09m

$323

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 7/9

5:55 am-3:07 pm

1 stop10h 12m

Winnipeg

Wed 7/15

12:46 pm-11:55 pm

1 stop10h 09m

$323

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 7/16

6:00 am-11:15 am

1 stop6h 15m

Winnipeg

Tue 7/21

12:20 pm-9:27 pm

2 stops8h 07m

$334

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 7/9

5:45 am-4:20 pm

2 stops11h 35m

Winnipeg

Tue 7/14

5:00 am-11:52 am

1 stop5h 52m

$334

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 9/4

11:15 am-8:09 pm

1 stop9h 54m

Winnipeg

Sun 9/13

12:40 pm-10:20 pm

1 stop8h 40m

$345
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/22

6:00 am-11:12 am

1 stop6h 12m

Winnipeg

Sat 10/24

5:10 am-11:55 am

1 stop5h 45m

$366

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/9

10:40 am-3:09 pm

1 stop5h 29m

Winnipeg

Sat 9/12

5:10 am-6:07 pm

2 stops11h 57m

$370

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 10/14

10:05 am-5:58 pm

2 stops8h 53m

Winnipeg

Wed 10/21

9:20 am-5:35 pm

1 stop7h 15m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Showing 1-10 of 21 resultsSorted by cheapest first
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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, June is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of $110). 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.

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?

    Delta, United Airlines, and Air Canada can get you from Massachusetts to Winnipeg in just under 6h 15m. Your travel time can differ by up to 4h 48m. 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, June is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of $110). 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

Browse thousands of different options on Cheapflights for your next trip

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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 May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$143Average$420FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$149Average$644FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$194Average$508FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$409Average$493FlexibilityNo cancel feeOn-time52%

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