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$103+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$252
(United Airlines)

One-way from

$103
(United Airlines)

Popular in

April

Cheapest in

January

Average price

$770
Provider with most accurate pricing for Boston Logan Intl-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Winnipeg flights.
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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. 23% potential increase in price ($151 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This United Airlines deal was found by Cheapflights users on 4/23. 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.
Sun 5/256:00 amBOS - YWG
1 stop17h 33mUnited Airlines
Sat 6/145:00 amYWG - BOS
1 stop5h 23mUnited Airlines
Deal found 4/23$252
This Delta deal was found by Cheapflights users on 4/23. 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.
Wed 6/1111:16 amBOS - YWG
1 stop9h 56mDelta
Fri 6/1312:26 pmYWG - BOS
1 stop8h 54mDelta
Deal found 4/23$275
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 8/16:00 amBOS - YWG
1 stop11h 23mMultiple Airlines
Sun 8/106:30 amYWG - BOS
2 stops14h 42mMultiple Airlines
Deal found 4/23$354
This Air Canada deal was found by Cheapflights users on 4/23. 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 10/253:20 pmBOS - YWG
1 stop5h 55mAir Canada
Wed 10/298:00 amYWG - BOS
1 stop7h 58mAir Canada
Deal found 4/23$368
This FlightHub deal was found by Cheapflights users on 4/23. 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.
Sat 11/84:15 pmBOS - YWG
1 stop5h 54mPorter Airlines
Sat 11/1511:35 amYWG - BOS
1 stop5h 40mPorter Airlines
Deal found 4/23$419

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 April 24, 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

Sun 5/25

6:00 am-10:33 pm

1 stop17h 33m

Winnipeg

Sat 6/14

5:00 am-11:23 am

1 stop5h 23m

$252

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 6/11

11:16 am-8:12 pm

1 stop9h 56m

Winnipeg

Fri 6/13

12:26 pm-10:20 pm

1 stop8h 54m

$275

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 8/1

6:00 am-4:23 pm

1 stop11h 23m

Winnipeg

Sun 8/10

6:30 am-10:12 pm

2 stops14h 42m

$354

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 8/11

5:50 am-3:04 pm

1 stop10h 14m

Winnipeg

Wed 8/13

5:00 am-11:28 am

1 stop5h 28m

$430

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 6/2

6:55 pm-10:26 am

2 stops16h 31m

Winnipeg

Sun 6/8

11:45 am-9:31 pm

2 stops8h 46m

$689

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 5/25

6:00 am-10:33 pm

1 stop17h 33m

$103

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 7/31

8:05 am-4:51 pm

1 stop9h 46m

$110

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/21

6:00 am-3:31 pm

1 stop10h 31m

$112

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 8/2

6:00 am-5:38 pm

1 stop12h 38m

$143

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 8/1

6:00 am-4:23 pm

1 stop11h 23m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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 April is currently the most expensive (average of $506). 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 April 24, 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.

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

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 April 24, 2025.
Porter Airlines
8.0
Very good
284 reviews

Crew

8.8

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
284 reviews
Porter Airlines
8.0
Very good
284 reviews

Crew

8.8

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,920 reviews
Porter Airlines
8.0
Very good
284 reviews

Crew

8.8

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,685 reviews
Porter Airlines
8.0
Very good
284 reviews

Crew

8.8

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,192 reviews
Porter Airlines
8.0
Very good
284 reviews

Crew

8.8

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Lufthansa
6.7
Okay
7,027 reviews
Porter Airlines
8.0
Very good
284 reviews

Crew

8.8

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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 United Airlines, with whom users have recently found tickets for as low as $103. However, be on the lookout for offers from Delta and Lufthansa, 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 April is currently the most expensive (average of $506). 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

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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$134Average$464FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$172Average$586FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$283Average$417FlexibilityNo cancel feeOn-time52%
DeltaCheapest$347Average$744FlexibilityNo cancel feeOn-timeN/A

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