Massachusetts

$132+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Jan 15 — Jan 221
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to Massachusetts with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 16, 2025.

This United Airlines deal was found by Cheapflights users on 12/13. 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.
Thu 12/252:20 pmYWG - ALB
1 stop5h 45mUnited Airlines
Thu 1/16:00 amALB - YWG
1 stop6h 57mUnited Airlines
Deal found 12/13$671

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 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$263
(Kiwi.com)

One-way from

$132
(Kiwi.com)

Popular in

December

Cheapest in

June

Average price

$583
Provider with most accurate pricing for Winnipeg-Boston Logan Intl flight deals.
Provider most trusted by Cheapflights users for Winnipeg-Boston Logan Intl flights.
From Winnipeg to Massachusetts
One-way flight from Winnipeg to Massachusetts
Highest demand for flights based on searches. 21% potential increase in price ($112 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Average for round-trip flights in December 2025

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 16, 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

Mon 1/12

8:00 am-11:57 pm

1 stop14h 57m

Boston Logan Intl

Mon 1/19

5:34 am-6:03 pm

1 stop13h 29m

$263

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 1/30

12:55 pm-1:13 am

2 stops35h 18m

Boston Logan Intl

Fri 2/6

6:00 am-3:09 pm

1 stop10h 09m

$290

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 1/15

5:00 am-11:05 am

1 stop29h 05m

Boston Logan Intl

Thu 1/22

6:00 am-12:41 am

2 stops19h 41m

$308

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 1/15

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Thu 1/22

10:15 am-4:35 pm

1 stop7h 20m

$318

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 2/13

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Sun 2/15

5:30 am-10:15 am

1 stop5h 45m

$329

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Mon 3/2

2:20 pm-9:16 pm

1 stop5h 56m

Albany Intl

Wed 3/4

7:30 pm-11:57 am

2 stops17h 27m

$353

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Fri 1/23

5:30 am-9:22 pm

2 stops14h 52m

Albany Intl

Sun 1/25

6:00 am-11:57 am

1 stop6h 57m

$413

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Fri 1/23

7:30 am-1:24 pm

1 stop28h 54m

Albany Intl

Sun 1/25

6:00 am-3:07 pm

1 stop10h 07m

$466

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 1/30

6:55 pm-1:13 am

3 stops29h 18m

$132

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 6/4

11:45 am-6:28 pm

1 stop5h 43m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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 $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 16, 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.

Food

7.3

Entertainment

7.9

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

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.

Food

7.3

Entertainment

7.9

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

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.

Food

7.3

Entertainment

7.9

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

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.

Food

7.3

Entertainment

7.9

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

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?

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.

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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$310FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$212Average$419FlexibilityNo cancel feeOn-time67%
DeltaCheapest$241Average$605FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.