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$156+ Cheap flights from Winnipeg (YWG) to Massachusetts

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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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Cheap flight deals from Winnipeg to Massachusetts

Keep the following information in mind while searching for Winnipeg to Massachusetts flight deals. Data was last updated April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$280
(Delta)

One-way from

$156
(United Airlines)

Popular in

December

Cheapest in

October

Average price

$354
Provider with most accurate pricing for Winnipeg-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Winnipeg-Boston Logan Intl flights.
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From Winnipeg to Massachusetts
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One-way flight from Winnipeg to Massachusetts
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Highest demand for flights based on searches. 20% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($20 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 Winnipeg to Massachusetts

Cheapest flights from Winnipeg to Massachusetts
Explore the most affordable flight options available from Winnipeg to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2025.

This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1012:26 pmYWG - BOS
2 stops10h 27mDelta
Wed 8/65:35 amBOS - YWG
1 stop6h 56mDelta
Deal found 4/28$280
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/212:20 pmYWG - BOS
2 stops8h 39mUnited Airlines
Tue 5/276:00 amBOS - YWG
1 stop10h 31mUnited Airlines
Deal found 4/28$288
This Air Canada deal was found by Cheapflights users on 4/29. 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 7/105:00 amYWG - BOS
1 stop5h 28mAir Canada
Wed 8/610:40 amBOS - YWG
1 stop7h 58mAir Canada
Deal found 4/29$299
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2511:45 amYWG - BOS
2 stops9h 16mPorter Airlines
Fri 8/13:50 pmBOS - YWG
1 stop7h 56mPorter Airlines
Deal found 4/28$355
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 6/711:45 amYWG - BOS
2 stops20h 24mMultiple Airlines
Wed 6/113:50 pmBOS - YWG
1 stop7h 56mMultiple Airlines
Deal found 4/28$385

Cheapflights Fare Finder

Customize your flight search to find flights from Winnipeg to Massachusetts 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 30, 2025.
Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

Fly from

Winnipeg

Fly to

Massachusetts

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 7/10

12:26 pm-11:53 pm

2 stops10h 27m

Boston Logan Intl

Wed 8/6

5:35 am-11:31 am

1 stop6h 56m

$280

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 5/21

2:20 pm-11:59 pm

2 stops8h 39m

Boston Logan Intl

Tue 5/27

6:00 am-3:31 pm

1 stop10h 31m

$288

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 7/10

5:00 am-11:28 am

1 stop5h 28m

Boston Logan Intl

Wed 8/6

10:40 am-5:38 pm

1 stop7h 58m

$299

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 7/25

11:45 am-10:01 pm

2 stops9h 16m

Boston Logan Intl

Fri 8/1

3:50 pm-10:46 pm

1 stop7h 56m

$355

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 6/7

11:45 am-9:09 am

2 stops20h 24m

Boston Logan Intl

Wed 6/11

3:50 pm-10:46 pm

1 stop7h 56m

$385

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 6/12

2:20 pm-12:59 am

1 stop9h 39m

$156

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 9/1

8:00 am-2:31 pm

1 stop5h 31m

$171

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 9/1

12:40 pm-1:06 am

2 stops11h 26m

$183

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 9/11

9:00 am-11:29 pm

2 stops13h 29m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Best time to book a flight from Winnipeg to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Winnipeg 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 Winnipeg to Massachusetts

What is the cheapest month to book a flight from Winnipeg to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $218). Flying from Winnipeg to Massachusetts in July is currently the most expensive (average of $311). 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 YWG to MA?

Find hourly flight availability from Winnipeg to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 30, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Massachusetts as you normally would.

Rainfall in Massachusetts by month

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

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

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

If weather is an important factor for your trip to Massachusetts, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated April 30, 2025.
Porter Airlines
8.0
Very good
285 reviews

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.8

Food

7.6

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
285 reviews
Porter Airlines
8.0
Very good
285 reviews

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.8

Food

7.6

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
7,936 reviews
Porter Airlines
8.0
Very good
285 reviews

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.8

Food

7.6

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
8,696 reviews
Porter Airlines
8.0
Very good
285 reviews

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.8

Food

7.6

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
9,242 reviews
Porter Airlines
8.0
Very good
285 reviews

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.8

Food

7.6

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 Winnipeg to Massachusetts. 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 from for flights from Winnipeg to Massachusetts?

    For a flight from Winnipeg to Massachusetts, you will be flying from Winnipeg. Winnipeg (YWG) is just 4.6 mi from the center of the city.

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

    $156 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Air Canada and Delta, with prices starting from $171 and $183, respectively.

  • What are the most popular routes from Winnipeg to Massachusetts?

    The most popular route from Winnipeg to Massachusetts is Winnipeg - Boston Logan Intl. You may also consider Winnipeg - Albany Intl or Winnipeg - Provincetown.

  • Can I find deals for flights from Winnipeg to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Massachusetts.

  • Can I find deals for business class flights from Winnipeg to Massachusetts?

    Yes. Cheapflights offers flight deals from Winnipeg to Massachusetts 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 Winnipeg to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $218). Flying from Winnipeg to Massachusetts in July is currently the most expensive (average of $311). 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 3 airlines flying from Winnipeg to Massachusetts

Discover the top 3 airlines that operate flights from Winnipeg to Massachusetts. 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$331FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$254Average$422FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$267Average$355FlexibilityNo cancel feeOn-time52%

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