HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$173+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Winnipeg with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 24, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Sat 9/510:05 am
BOS
-
YWG
1 stop6h 14m
Multiple Airlines
Wed 9/96:15 am
YWG
-
BOS
1 stop9h 31m
Multiple Airlines
Deal found 6/19$347
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 9/48:10 pm
BOS
-
YWG
1 stop14h 35m
Multiple Airlines
Tue 9/86:05 pm
YWG
-
BOS
1 stop15h 25m
Multiple Airlines
Deal found 6/19$351
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Sat 9/510:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Tue 9/811:15 am
YWG
-
BOS
2 stops22h 15m
Porter Airlines
Deal found 6/19$352
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 9/1610:05 am
BOS
-
YWG
1 stop8h 10m
Multiple Airlines
Thu 9/178:45 pm
YWG
-
BOS
1 stop11h 20m
Multiple Airlines
Deal found 6/22$353
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 8/195:30 pm
BOS
-
YWG
1 stop17h 15m
Multiple Airlines
Tue 8/2511:15 am
YWG
-
BOS
2 stops22h 15m
Multiple Airlines
Deal found 6/21$357
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 8/118:10 pm
BOS
-
YWG
1 stop14h 35m
Multiple Airlines
Mon 8/3111:15 am
YWG
-
BOS
2 stops22h 15m
Multiple Airlines
Deal found 6/20$358
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 8/1411:10 am
BOS
-
YWG
1 stop10h 20m
Multiple Airlines
Tue 8/256:15 am
YWG
-
BOS
1 stop9h 31m
Multiple Airlines
Deal found 6/21$360
This Kiwi.com deal was found by Cheapflights users on 6/21. 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.
Sat 8/155:30 pm
BOS
-
YWG
1 stop18h 49m
Porter Airlines
Tue 8/2511:15 am
YWG
-
BOS
2 stops22h 15m
Porter Airlines
Deal found 6/21$365
This Trip.com deal was found by Cheapflights users on 6/21. 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 7/910:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Wed 7/1512:15 pm
YWG
-
BOS
1 stop5h 20m
Porter Airlines
Deal found 6/21$367

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 June 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$347
(Kiwi.com)

One-way from

$173
(Trip.com)

Popular in

February

Cheapest in

August

Average price

$548
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. 23% potential increase in price ($179 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 24, 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 9/4

8:10 pm-9:45 am

1 stop14h 35m

Winnipeg

Tue 9/8

6:05 pm-10:30 am

1 stop15h 25m

$351

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 9/5

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Tue 9/8

6:15 am-4:46 pm

1 stop9h 31m

$352

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/16

10:05 am-5:15 pm

1 stop8h 10m

Winnipeg

Thu 9/17

6:00 am-6:35 pm

2 stops11h 35m

$357

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 8/28

7:30 pm-9:45 am

1 stop15h 15m

Winnipeg

Sat 9/5

11:15 am-10:30 am

2 stops22h 15m

$358
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 8/13

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Thu 8/27

12:15 pm-6:35 pm

1 stop5h 20m

$371

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 8/28

7:10 am-5:58 pm

2 stops11h 48m

Winnipeg

Sat 9/5

4:15 pm-9:05 am

2 stops15h 50m

$373

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 7/24

7:30 pm-9:45 am

1 stop15h 15m

Winnipeg

Tue 7/28

6:15 am-6:35 pm

1 stop11h 20m

$381

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 8/11

8:10 pm-10:43 am

2 stops15h 33m

Winnipeg

Mon 8/31

4:15 pm-9:05 am

2 stops15h 50m

$385

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 8/19

4:45 pm-9:45 am

2 stops18h 00m

Winnipeg

Tue 8/25

4:15 pm-10:30 am

2 stops17h 15m

$391

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 9/27

10:05 am-4:25 pm

1 stop7h 20m

Winnipeg

Sat 10/3

11:15 am-10:30 am

2 stops22h 15m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/20

Showing 1-10 of 17 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 $111). Flying from Massachusetts to Winnipeg in September is currently the most expensive (average of $331). 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?

    Porter Airlines can get you from Massachusetts to Winnipeg in just under 6h 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, May is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of $111). Flying from Massachusetts to Winnipeg in September is currently the most expensive (average of $331). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 June 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$149Average$667FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$194Average$525FlexibilityNo cancel feeOn-time67%
DeltaCheapest$254Average$626FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$293Average$493FlexibilityNo cancel feeOn-time52%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.