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$152+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
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 septiembre 11, 2025.

Round-trip from

$226
(Kiwi.com)

One-way from

$152
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$345
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. 23% potential increase in price ($125 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
mié. 11/127:30 amYWG - BOS
1 stop24h 30mMultiple Airlines
sáb. 11/1511:43 amBOS - YWG
1 stop28h 24mMultiple Airlines
Deal found 9/9$226
This Air Canada deal was found by Cheapflights users on 9/9. 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.
sáb. 10/2511:15 amYWG - BOS
1 stop5h 40mAir Canada
sáb. 11/15:30 amBOS - YWG
1 stop5h 46mAir Canada
Deal found 9/9$258
This Delta deal was found by Cheapflights users on 9/9. 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.
sáb. 10/258:45 amYWG - BOS
1 stop9h 45mDelta
sáb. 11/112:00 pmBOS - YWG
2 stops12h 27mDelta
Deal found 9/9$278
This Air Canada deal was found by Cheapflights users on 9/10. 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.
sáb. 11/221:45 pmYWG - BOS
1 stop6h 42mAir Canada
dom. 11/305:30 amBOS - YWG
1 stop5h 46mAir Canada
Deal found 9/10$313
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
vie. 10/246:30 amYWG - BOS
1 stop10h 10mMultiple Airlines
dom. 11/28:24 pmBOS - YWG
2 stops29h 18mMultiple Airlines
Deal found 9/10$315
This Delta deal was found by Cheapflights users on 9/10. 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.
jue. 9/2512:44 pmYWG - BOS
1 stop10h 15mDelta
mar. 9/3011:40 amBOS - YWG
1 stop9h 31mDelta
Deal found 9/10$316
This Delta deal was found by Cheapflights users on 9/11. 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.
mar. 10/75:40 pmYWG - BOS
1 stop5h 19mDelta
mié. 10/155:45 amBOS - YWG
1 stop6h 45mDelta
Deal found 9/11$318
This Air Canada deal was found by Cheapflights users on 9/11. 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.
vie. 10/245:00 amYWG - BOS
1 stop5h 29mAir Canada
dom. 11/25:30 amBOS - YWG
1 stop5h 46mAir Canada
Deal found 9/11$319
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
vie. 9/269:00 amYWG - BOS
1 stop21h 43mMultiple Airlines
lun. 9/297:00 pmBOS - YWG
2 stops17h 41mMultiple Airlines
Deal found 9/10$352

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 septiembre 11, 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

sáb. 10/25

11:15 am-5:55 pm

1 stop5h 40m

Boston Logan Intl

sáb. 11/1

5:30 am-10:16 am

1 stop5h 46m

$258

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 10/25

8:45 am-7:30 pm

1 stop9h 45m

Boston Logan Intl

sáb. 11/1

12:00 pm-11:27 pm

2 stops12h 27m

$278

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 11/22

1:45 pm-9:27 pm

1 stop6h 42m

Boston Logan Intl

dom. 11/30

5:30 am-10:16 am

1 stop5h 46m

$313

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

vie. 10/24

6:30 am-5:40 pm

1 stop10h 10m

Boston Logan Intl

dom. 11/2

8:24 pm-12:42 am

2 stops29h 18m

$315

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

vie. 9/26

12:44 pm-11:59 pm

1 stop10h 15m

Boston Logan Intl

mar. 9/30

11:40 am-8:11 pm

1 stop9h 31m

$316

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 9/27

6:40 am-5:17 pm

1 stop9h 37m

Boston Logan Intl

lun. 9/29

7:05 am-4:50 pm

1 stop10h 45m

$316

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

jue. 9/25

12:44 pm-11:59 pm

1 stop10h 15m

Boston Logan Intl

mar. 9/30

11:40 am-8:11 pm

1 stop9h 31m

$316

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

vie. 9/26

12:44 pm-11:59 pm

1 stop10h 15m

Boston Logan Intl

dom. 9/28

8:10 am-4:50 pm

1 stop9h 40m

$316

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

jue. 9/25

12:44 pm-11:59 pm

1 stop10h 15m

Boston Logan Intl

lun. 9/29

7:05 am-4:50 pm

1 stop10h 45m

$316

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 9/27

6:40 am-7:21 pm

2 stops11h 41m

Boston Logan Intl

mar. 9/30

9:00 am-8:11 pm

2 stops12h 11m

$318

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 19 results
1
2

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.

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 septiembre 11, 2025.
Read reviews from past customers who have flown Delta, Porter Airlines, and United Airlines from Winnipeg to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Porter Airlines
7.9
Good
363 reviews
Delta
8.0
Very good
7,960 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Air Canada
7.1
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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.

  • How long is the flight from Winnipeg to Massachusetts?

    There are many flights that can get you from Winnipeg to Massachusetts in 5h 40m. Fly via Air Canada or Delta to get the fastest option. The distance from Winnipeg to Massachusetts is about 1350 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 4 airlines flying from Winnipeg to Massachusetts

Discover the top 4 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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$369FlexibilityNo cancel feeOn-time69%
DeltaCheapest$241Average$464FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$254Average$419FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$267Average$355FlexibilityNo cancel feeOn-time52%

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