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$202+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$338
(Air Canada)

One-way from

$202
(United Airlines)

Popular in

December

Cheapest in

June

Average price

$355
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. 22% potential increase in price ($119 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in October 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 octubre 30, 2025.

This Air Canada deal was found by Cheapflights users on 10/29. 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.
lun. 11/245:30 amYWG - BOS
1 stop9h 27mAir Canada
mar. 12/25:30 amBOS - YWG
1 stop5h 46mAir Canada
Deal found 10/29$338
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/277:30 amYWG - BOS
2 stops16h 14mMultiple Airlines
mar. 12/212:44 pmBOS - YWG
1 stop27h 23mMultiple Airlines
Deal found 10/29$383
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/278:20 pmYWG - BOS
1 stop12h 15mMultiple Airlines
jue. 12/47:00 amBOS - YWG
1 stop13h 35mMultiple Airlines
Deal found 10/29$392
This Air Canada deal was found by Cheapflights users on 10/29. 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.
jue. 11/278:15 amYWG - BOS
1 stop5h 37mAir Canada
mar. 12/210:15 amBOS - YWG
1 stop7h 20mAir Canada
Deal found 10/29$439
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/246:40 amYWG - BOS
2 stops12h 20mDelta
mar. 12/25:45 amBOS - YWG
1 stop7h 00mDelta
Deal found 10/29$462
This Air Canada deal was found by Cheapflights users on 10/30. 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.
vie. 11/217:05 pmYWG - BOS
1 stop16h 07mAir Canada
lun. 12/15:30 amBOS - YWG
2 stops12h 49mAir Canada
Deal found 10/30$497

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 octubre 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

jue. 11/27

7:30 am-12:44 am

2 stops16h 14m

Boston Logan Intl

mar. 12/2

12:44 pm-3:07 pm

1 stop27h 23m

$383

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

jue. 11/27

8:20 pm-9:35 am

1 stop12h 15m

Boston Logan Intl

jue. 12/4

7:00 am-7:35 pm

1 stop13h 35m

$392

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

jue. 11/27

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

mar. 12/2

10:15 am-4:35 pm

1 stop7h 20m

$439

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

mié. 3/25

2:15 pm-12:16 am

1 stop9h 01m

Albany Intl

jue. 3/26

6:15 am-11:39 am

1 stop6h 24m

$450

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

vie. 11/21

7:05 pm-12:12 pm

1 stop16h 07m

Boston Logan Intl

lun. 12/1

5:30 am-5:19 pm

2 stops12h 49m

$497

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

lun. 11/24

5:30 am-2:52 pm

2 stops8h 22m

Boston Logan Intl

mar. 12/2

3:40 pm-11:54 pm

2 stops9h 14m

$521

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

sáb. 12/13

2:20 pm-11:43 pm

2 stops8h 23m

$202

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 12/13

12:35 pm-11:24 pm

2 stops9h 49m

$249

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 12/13

2:20 pm-9:45 pm

1 stop6h 25m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $164). Flying from Winnipeg to Massachusetts in December is currently the most expensive (average of $358). 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 octubre 30, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and Air Canada from Winnipeg to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,993 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Delta
7.9
Good
7,993 reviews
Delta
7.9
Good
7,993 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,993 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Air Canada
7.1
Good
10,377 reviews
Delta
7.9
Good
7,993 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!

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 9h 01m. Fly via United Airlines to get the fastest option. The distance from Winnipeg to Massachusetts is about 1215 mi.

  • 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, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $164). Flying from Winnipeg to Massachusetts in December is currently the most expensive (average of $358). 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$369FlexibilityNo cancel feeOn-time69%
DeltaCheapest$241Average$560FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$254Average$419FlexibilityNo cancel feeOn-time67%

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