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$135+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Flightnetwork deal was found by Cheapflights users on 1/28. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:30 am
BOS
-
YWG
1 stop5h 45m
Air Canada
Sat 2/286:00 am
YWG
-
BOS
2 stops7h 52m
Air Canada
Deal found 1/28$344
This Mytrip deal was found by Cheapflights users on 1/27. 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.
Tue 2/246:10 pm
BOS
-
YWG
2 stops22h 20m
Multiple Airlines
Tue 3/38:20 pm
YWG
-
BOS
2 stops24h 41m
Multiple Airlines
Deal found 1/27$359
This Booking.com deal was found by Cheapflights users on 1/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:15 am
BOS
-
YWG
1 stop12h 04m
Air Canada
Fri 3/205:30 am
YWG
-
BOS
1 stop9h 27m
Air Canada
Deal found 1/27$400
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/254:23 pm
BOS
-
YWG
2 stops20h 09m
Multiple Airlines
Mon 3/308:00 am
YWG
-
BOS
1 stop14h 59m
Multiple Airlines
Deal found 1/27$408
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sun 3/153:30 pm
BOS
-
YWG
2 stops21h 02m
Multiple Airlines
Sun 3/227:30 am
YWG
-
BOS
1 stop27h 11m
Multiple Airlines
Deal found 1/28$429
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/273:30 pm
BOS
-
YWG
2 stops10h 09m
Multiple Airlines
Mon 3/308:00 am
YWG
-
BOS
1 stop14h 59m
Multiple Airlines
Deal found 1/27$437

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$344
(Flightnetwork)

One-way from

$135
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$574
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. 20% potential increase in price ($112 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 29, 2026.
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

Tue 2/24

6:10 pm-3:30 pm

2 stops22h 20m

Winnipeg

Tue 3/3

8:20 pm-11:05 am

1 stop13h 45m

$363

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 3/13

6:15 am-5:19 pm

1 stop12h 04m

Winnipeg

Fri 3/20

5:30 am-7:12 pm

3 stops12h 42m

$404

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 3/26

3:30 pm-12:39 am

2 stops10h 09m

Winnipeg

Mon 3/30

8:00 am-11:59 pm

1 stop14h 59m

$425

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 3/15

3:30 pm-11:32 am

2 stops21h 02m

Winnipeg

Sun 3/22

7:30 am-11:41 am

1 stop27h 11m

$429

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 3/13

6:15 am-11:47 pm

2 stops18h 32m

Winnipeg

Fri 3/20

6:00 am-7:12 pm

3 stops12h 12m

$472

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 3/26

8:45 pm-3:09 pm

1 stop19h 24m

Winnipeg

Mon 3/30

8:00 am-10:19 am

1 stop25h 19m

$550

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 2/24

6:25 pm-7:09 pm

2 stops25h 44m

Winnipeg

Tue 3/3

5:00 am-3:53 pm

2 stops9h 53m

$550

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 6/14

5:30 am-5:15 pm

2 stops12h 45m

Winnipeg

Sat 6/20

6:15 am-10:20 pm

2 stops15h 05m

$560

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 3/25

9:05 am-7:09 pm

2 stops11h 04m

Winnipeg

Tue 3/31

5:00 am-6:27 pm

2 stops12h 27m

$572

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 4/30

12:35 pm-8:15 pm

3 stops32h 40m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 15 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, 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 $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.

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 12h 04m. 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 $118). 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$128Average$426FlexibilityNo cancel feeOn-time67%
DeltaCheapest$131Average$420FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$172Average$586FlexibilityNo cancel feeOn-time69%

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