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$164+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 December 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/221:30 pmYWG - BOS
1 stop8h 07mUnited Airlines
Wed 12/316:15 amBOS - YWG
1 stop7h 24mUnited Airlines
Deal found 12/11$593
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Wed 12/177:30 amYWG - BOS
1 stop25h 38mMultiple Airlines
Wed 12/243:40 pmBOS - YWG
2 stops28h 55mMultiple Airlines
Deal found 12/10$732
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/172:20 pmYWG - BOS
2 stops8h 21mUnited Airlines
Wed 12/242:15 pmBOS - YWG
2 stops22h 42mUnited Airlines
Deal found 12/10$756
This American Airlines deal was found by Cheapflights users on 12/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:00 amYWG - BOS
2 stops13h 26mAmerican Airlines
Wed 12/312:14 pmBOS - YWG
2 stops34h 21mAmerican Airlines
Deal found 12/11$812
This Delta deal was found by Cheapflights users on 12/11. 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.
Mon 12/225:45 pmYWG - BOS
1 stop5h 09mDelta
Wed 12/313:15 pmBOS - YWG
1 stop9h 29mDelta
Deal found 12/11$929
This American Airlines deal was found by Cheapflights users on 12/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1712:10 pmYWG - BOS
3 stops21h 56mAmerican Airlines
Wed 12/246:15 amBOS - YWG
2 stops42h 20mAmerican Airlines
Deal found 12/10$1,106

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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$225
(Kiwi.com)

One-way from

$164
(Trip.com)

Popular in

December

Cheapest in

June

Average price

$557
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. 20% potential increase in price ($106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 12, 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

Wed 1/21

7:30 am-1:03 am

1 stop16h 33m

Boston Logan Intl

Wed 1/28

6:00 am-12:41 am

2 stops19h 41m

$236

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 1/15

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Wed 1/21

10:15 am-4:35 pm

1 stop7h 20m

$295

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 1/15

8:20 pm-8:30 pm

1 stop23h 10m

Boston Logan Intl

Wed 1/21

6:00 am-3:07 pm

1 stop10h 07m

$301

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 2/27

7:30 am-1:04 am

1 stop16h 34m

Boston Logan Intl

Sat 3/14

10:52 am-3:09 pm

1 stop29h 17m

$307

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 3/22

7:30 am-9:57 am

1 stop25h 27m

Boston Logan Intl

Wed 4/1

6:00 am-3:09 pm

1 stop10h 09m

$325

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 2/5

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Mon 2/9

5:30 am-10:15 am

1 stop5h 45m

$327

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 3/4

7:30 am-12:05 am

1 stop15h 35m

Boston Logan Intl

Sat 3/14

3:30 pm-11:32 am

2 stops21h 02m

$338

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 3/5

5:00 am-6:10 pm

2 stops12h 10m

Boston Logan Intl

Sat 3/14

10:52 am-3:09 pm

1 stop29h 17m

$348

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Mon 3/2

2:20 pm-9:21 pm

1 stop6h 01m

Albany Intl

Wed 3/4

7:30 pm-11:57 am

2 stops17h 27m

$352

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 3/23

5:00 am-2:45 pm

1 stop8h 45m

Boston Logan Intl

Wed 4/1

10:52 am-12:40 am

2 stops14h 48m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 22 results
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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 $161). Flying from Winnipeg to Massachusetts in March is currently the most expensive (average of $328). 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 December 12, 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
8,009 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.1

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
8,009 reviews
Delta
7.9
Good
8,009 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.1

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
9,095 reviews
Delta
7.9
Good
8,009 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.1

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
10,514 reviews
Delta
7.9
Good
8,009 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.1

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 5h 37m. Fly via Air Canada or United Airlines 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, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $161). Flying from Winnipeg to Massachusetts in March is currently the most expensive (average of $328). 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$301FlexibilityNo cancel feeOn-time69%
DeltaCheapest$241Average$605FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$254Average$415FlexibilityNo cancel feeOn-time67%

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