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$177+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Ogos 6 — Ogos 131
Rabu 8/6
Rabu 8/13
1 adult, Economy
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Cheap flight deals from Massachusetts to Winnipeg

Keep the following information in mind while searching for Massachusetts to Winnipeg flight deals. Data was last updated Ogos 1, 2025.

Round-trip from

$357
(Delta)

One-way from

$177
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$420
From Massachusetts to Winnipeg
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One-way flight from Massachusetts to Winnipeg
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Highest demand for flights based on searches. 19% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 Ogos 1, 2025.

This Delta deal was found by Cheapflights users on 7/30. 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.
Khamis 8/215:40 amBOS - YWG
1 stop7h 13mDelta
Selasa 8/265:41 pmYWG - BOS
1 stop5h 37mDelta
Deal found 7/30$357
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Khamis 8/217:45 amBOS - YWG
1 stop15h 48mUnited Airlines
Selasa 8/267:00 amYWG - BOS
1 stop6h 40mUnited Airlines
Deal found 7/31$385
This Air Canada deal was found by Cheapflights users on 7/30. 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.
Khamis 8/215:50 amBOS - YWG
2 stops12h 50mAir Canada
Isnin 8/256:35 pmYWG - BOS
2 stops13h 55mAir Canada
Deal found 7/30$427
This FlightHub deal was found by Cheapflights users on 7/31. 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.
Isnin 8/43:30 pmBOS - YWG
1 stop8h 16mPorter Airlines
Isnin 8/1811:45 amYWG - BOS
1 stop5h 43mPorter Airlines
Deal found 7/31$898
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Jumaat 8/18:39 pmBOS - YWG
3 stops28h 34mMultiple Airlines
Selasa 8/56:55 pmYWG - BOS
3 stops22h 33mMultiple Airlines
Deal found 7/30$943

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 Ogos 1, 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

Khamis 8/21

5:40 am-11:53 am

1 stop7h 13m

Winnipeg

Selasa 8/26

5:41 pm-12:18 am

1 stop5h 37m

$357

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Khamis 8/21

7:45 am-10:33 pm

1 stop15h 48m

Winnipeg

Selasa 8/26

7:00 am-2:40 pm

1 stop6h 40m

$385

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Khamis 8/21

5:50 am-5:40 pm

2 stops12h 50m

Winnipeg

Selasa 8/26

8:10 pm-9:30 am

2 stops12h 20m

$427

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Selasa 8/12

6:15 pm-10:46 pm

2 stops29h 31m

$177

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Khamis 11/27

10:15 am-4:35 pm

1 stop7h 20m

$236

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Jumaat 8/15

3:30 pm-10:46 pm

1 stop8h 16m

$300

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Khamis 11/27

7:50 am-11:44 pm

3 stops16h 54m

$495

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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, August is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of $358). Flying from Massachusetts to Winnipeg in December is currently the most expensive (average of $497). 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 Ogos 1, 2025.

When flying from Massachusetts to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated Ogos 1, 2025.
See what other customers who have flown with Porter Airlines, Delta, and United Airlines from Massachusetts to Winnipeg have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Comfort

8.0

Crew

8.7

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Comfort

8.0

Crew

8.7

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,981 reviews
Porter Airlines
8.0
Very good
318 reviews

Comfort

8.0

Crew

8.7

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,900 reviews
Porter Airlines
8.0
Very good
318 reviews

Comfort

8.0

Crew

8.7

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,851 reviews
Porter Airlines
8.0
Very good
318 reviews

Comfort

8.0

Crew

8.7

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • What are the cheapest airlines to fly from Massachusetts to Winnipeg one-way?

    The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as $236. However, be on the lookout for offers from Porter Airlines and United Airlines, as they are both options that can get you from Massachusetts to Winnipeg for a low price.

  • 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, August is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of $358). Flying from Massachusetts to Winnipeg in December is currently the most expensive (average of $497). 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 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 Ogos 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$134Average$426FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$172Average$569FlexibilityNo cancel feeOn-time69%
DeltaCheapest$274Average$458FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$283Average$438FlexibilityNo cancel feeOn-time52%

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