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Massachusetts

$183+ 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 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 3/117:30 am
YWG
-
BOS
1 stop27h 11m
Multiple Airlines
Tue 3/2412:36 pm
BOS
-
YWG
1 stop27h 33m
Multiple Airlines
Deal found 1/27$319
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sun 4/57:30 am
YWG
-
BOS
1 stop16h 56m
Multiple Airlines
Thu 4/95:40 am
BOS
-
YWG
2 stops14h 29m
Multiple Airlines
Deal found 1/27$353
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 4/17:30 am
YWG
-
BOS
1 stop16h 56m
Multiple Airlines
Thu 4/95:40 am
BOS
-
YWG
2 stops14h 29m
Multiple Airlines
Deal found 1/27$367
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sun 4/57:30 am
YWG
-
BOS
1 stop16h 56m
Multiple Airlines
Wed 4/83:30 pm
BOS
-
YWG
2 stops10h 09m
Multiple Airlines
Deal found 1/27$368
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 4/17:30 am
YWG
-
BOS
1 stop16h 56m
Multiple Airlines
Wed 4/83:30 pm
BOS
-
YWG
2 stops10h 09m
Multiple Airlines
Deal found 1/27$382
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 3/315:00 am
YWG
-
BOS
2 stops17h 59m
Multiple Airlines
Wed 4/810:20 am
BOS
-
YWG
1 stop9h 49m
Multiple Airlines
Deal found 1/27$384
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Mon 4/68:20 pm
YWG
-
BOS
1 stop12h 15m
Multiple Airlines
Thu 4/95:40 am
BOS
-
YWG
2 stops14h 29m
Multiple Airlines
Deal found 1/27$386
This FlightHub deal was found by Cheapflights users on 1/27. 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 7/1110:45 am
YWG
-
ALB
2 stops11h 21m
WestJet
Fri 9/41:15 pm
ALB
-
YWG
2 stops10h 45m
WestJet
Deal found 1/27$388
This Delta deal was found by Cheapflights users on 1/27. 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.
Tue 2/36:40 am
YWG
-
ALB
2 stops15h 15m
Delta
Thu 2/512:29 pm
ALB
-
YWG
2 stops12h 09m
Delta
Deal found 1/27$514
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 2/32:20 pm
YWG
-
ALB
1 stop6h 03m
United Airlines
Thu 2/57:25 pm
ALB
-
YWG
2 stops17h 32m
United Airlines
Deal found 1/27$560
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Sat 7/118:15 am
YWG
-
ALB
2 stops11h 47m
United Airlines
Fri 9/48:00 am
ALB
-
YWG
1 stop13h 48m
United Airlines
Deal found 1/28$723
This Air Canada deal was found by Cheapflights users on 1/26. 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.
Tue 2/32:20 pm
YWG
-
ALB
1 stop6h 03m
Air Canada
Thu 2/56:00 am
ALB
-
YWG
1 stop6h 57m
Air Canada
Deal found 1/26$725

Find flight deals from Winnipeg to Massachusetts

Keep the following information in mind while searching for Winnipeg to Massachusetts flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(Kiwi.com)

One-way from

$183
(Kiwi.com)

Popular in

January

Cheapest in

June

Average price

$550
Provider with most accurate pricing for Winnipeg-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Boston Logan Intl flights.
Search Deals
From Winnipeg to Massachusetts
Search Deals
One-way flight from Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($90 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Wed 3/11

7:30 am-11:41 am

1 stop27h 11m

Boston Logan Intl

Tue 3/24

12:36 pm-3:09 pm

1 stop27h 33m

$319

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 4/5

7:30 am-1:26 am

1 stop16h 56m

Boston Logan Intl

Thu 4/9

5:40 am-7:09 pm

2 stops14h 29m

$353

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 7/11

10:45 am-11:06 pm

2 stops11h 21m

Albany Intl

Fri 9/4

1:15 pm-11:00 pm

2 stops10h 45m

$388

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 3/31

8:05 pm-9:35 am

1 stop12h 30m

Boston Logan Intl

Thu 4/9

5:40 am-7:09 pm

2 stops14h 29m

$396

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 4/3

12:20 pm-10:05 pm

1 stop8h 45m

Boston Logan Intl

Thu 4/9

5:40 am-7:09 pm

2 stops14h 29m

$409

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 3/6

5:00 am-6:02 pm

1 stop12h 02m

Boston Logan Intl

Mon 3/9

6:10 pm-12:40 am

3 stops31h 30m

$412

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 4/2

5:00 am-2:45 pm

1 stop8h 45m

Boston Logan Intl

Wed 4/8

3:30 pm-12:39 am

2 stops10h 09m

$420

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 3/20

5:00 am-2:45 pm

1 stop8h 45m

Boston Logan Intl

Mon 3/23

3:30 pm-11:32 am

2 stops21h 02m

$434

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 7/11

8:15 am-9:02 pm

2 stops11h 47m

Albany Intl

Fri 9/4

8:00 am-8:48 pm

1 stop13h 48m

$723

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 7/11

8:15 am-9:02 pm

2 stops11h 47m

Albany Intl

Fri 9/4

4:30 pm-10:24 pm

1 stop6h 54m

$812

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 14 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, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $169). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of $426). 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 January 29, 2026.
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
8,127 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,127 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,215 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Air Canada
7.1
Good
10,667 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 11h 21m. Fly via WestJet, United Airlines, or Air Canada to get the fastest option. The distance from Winnipeg to Massachusetts is about 1215 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $144 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Air Canada and United Airlines, with prices starting from $146 and $171, 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, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $169). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of $426). 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.

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$369FlexibilityNo cancel feeOn-time69%
DeltaCheapest$182Average$605FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$212Average$419FlexibilityNo cancel feeOn-time67%

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