What is the cheapest airline that flies from Winnipeg to Massachusetts?

Air Canada is the most popular carrier operating from Winnipeg to Massachusetts

What airlines fly to Massachusetts?

Air Canada, United Airlines and Delta are the top three most popular airlines that fly to Massachusetts from Winnipeg according to our data. Air Canada is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 3 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Winnipeg Airport to Massachusetts?

Prices for flights from Winnipeg Airport to Massachusetts refresh daily.

How many operators does momondo search for flights from Winnipeg Airport to Massachusetts?

The number of operators available for flights from Winnipeg Airport to Massachusetts is 3 as of October 2025.

How old do you have to be to fly from Winnipeg Airport to Massachusetts?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Massachusetts.

What documentation or ID do you need to fly to Massachusetts?

The travel and health documents required for your trip to Massachusetts can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$165 Cheap Flights from Winnipeg to Massachusetts in 2025/26

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Find the cheapest flights from Winnipeg to Massachusetts

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:00 am - 2:55 pmYWG-BOS

8h 55m1 stop

9:54 pm - 3:07 pmBOS-YWG

18h 13m2 stops

$318Multiple Airlines

Find Deal

Tue, Nov 25 - Tue, Dec 2

8:20 pm - 9:35 amYWG-BOS

12h 15m1 stop

9:54 pm - 3:07 pmBOS-YWG

18h 13m2 stops

$325Multiple Airlines

Find Deal

Mon, Nov 24 - Tue, Dec 2

5:00 am - 2:55 pmYWG-BOS

8h 55m1 stop

9:54 pm - 3:07 pmBOS-YWG

18h 13m2 stops

$327Multiple Airlines

Find Deal

Tue, Nov 25 - Tue, Dec 2

2:20 pm - 9:14 pmYWG-ALB

5h 54m1 stop

7:35 pm - 11:57 amALB-YWG

17h 22m2 stops

$349United Airlines

Find Deal

Thu, Dec 11 - Mon, Dec 15

8:00 am - 9:14 pmYWG-ALB

12h 14m2 stops

6:00 am - 3:43 pmALB-YWG

10h 43m2 stops

$401Air Canada

Find Deal

Thu, Dec 11 - Mon, Dec 15

8:15 am - 2:52 pmYWG-BOS

5h 37m1 stop

5:30 am - 10:16 amBOS-YWG

5h 46m1 stop

$414Air Canada

Find Deal

Wed, Dec 10 - Wed, Dec 17

2:15 pm - 9:06 pmYWG-ALB

5h 51m1 stop

6:15 am - 11:39 amALB-YWG

6h 24m1 stop

$449United Airlines

Find Deal

Wed, Mar 25 - Thu, Mar 26

5:45 pm - 12:06 amYWG-BOS

5h 21m1 stop

3:15 pm - 11:44 pmBOS-YWG

9h 29m1 stop

$547Delta

Find Deal

Fri, Dec 19 - Mon, Dec 22

6:40 am - 5:08 pmYWG-BOS

9h 28m1 stop

6:25 pm - 3:07 pmBOS-YWG

21h 42m1 stop

$578Delta

Find Deal

Sat, Nov 29 - Sat, Dec 6

6:00 am - 10:49 pmYWG-ALB

15h 49m2 stops

5:11 pm - 11:35 pmALB-YWG

55h 24m3 stops

$641American Airlines

Find Deal

Thu, Dec 11 - Mon, Dec 15

Delta flights from Winnipeg to Massachusetts

Our best Delta deals on Winnipeg to Massachusetts flight tickets

Delta

Dec 19

YWG5:45 pmWinnipeg

5h 21m

1 stop

BOS12:06 amBoston Logan Intl

Dec 22

BOS3:15 pmBoston Logan Intl

9h 29m

1 stop

YWG11:44 pmWinnipeg

$547

Find similar

Delta

Nov 29

YWG6:40 amWinnipeg

9h 28m

1 stop

BOS5:08 pmBoston Logan Intl

Dec 6

BOS6:25 pmBoston Logan Intl

21h 42m

1 stop

YWG3:07 pmWinnipeg

$578

Find similar

Air Canada flights from Winnipeg to Massachusetts

Our best Air Canada deals on Winnipeg to Massachusetts flight tickets

Air Canada

Dec 11

YWG8:00 amWinnipeg

12h 14m

2 stops

ALB9:14 pmAlbany Intl

Dec 15

ALB6:00 amAlbany Intl

10h 43m

2 stops

YWG3:43 pmWinnipeg

$401

Find similar

Air Canada

Dec 10

YWG8:15 amWinnipeg

5h 37m

1 stop

BOS2:52 pmBoston Logan Intl

Dec 17

BOS5:30 amBoston Logan Intl

5h 46m

1 stop

YWG10:16 amWinnipeg

$414

Find similar

Air Canada

Nov 25

YWG5:30 amWinnipeg

12h 42m

2 stops

BOS7:12 pmBoston Logan Intl

Dec 2

BOS5:30 amBoston Logan Intl

5h 46m

1 stop

YWG10:16 amWinnipeg

$447

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 11/25

5:00 am-2:55 pm

1 stop8h 55m

Boston Logan Intl

Tue 12/2

9:54 pm-3:07 pm

2 stops18h 13m

$318

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 11/24

8:20 pm-9:35 am

1 stop12h 15m

Boston Logan Intl

Tue 12/2

9:54 pm-3:07 pm

2 stops18h 13m

$325

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 11/25

5:00 am-2:55 pm

1 stop8h 55m

Boston Logan Intl

Tue 12/2

9:54 pm-3:07 pm

2 stops18h 13m

$327

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Thu 12/11

2:20 pm-9:14 pm

1 stop5h 54m

Albany Intl

Mon 12/15

7:35 pm-11:57 am

2 stops17h 22m

$349

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Thu 12/11

8:00 am-9:14 pm

2 stops12h 14m

Albany Intl

Mon 12/15

6:00 am-3:43 pm

2 stops10h 43m

$401

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 12/10

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Wed 12/17

5:30 am-10:16 am

1 stop5h 46m

$414

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Wed 3/25

2:15 pm-9:06 pm

1 stop5h 51m

Albany Intl

Thu 3/26

6:15 am-11:39 am

1 stop6h 24m

$449

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 12/19

5:45 pm-12:06 am

1 stop5h 21m

Boston Logan Intl

Mon 12/22

3:15 pm-11:44 pm

1 stop9h 29m

$547

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 11/29

6:40 am-5:08 pm

1 stop9h 28m

Boston Logan Intl

Sat 12/6

6:25 pm-3:07 pm

1 stop21h 42m

$578

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Thu 12/11

6:00 am-10:49 pm

2 stops15h 49m

Albany Intl

Mon 12/15

5:11 pm-11:35 pm

3 stops55h 24m

$641

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first

How to get the cheapest flight ticket from Winnipeg to Massachusetts

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Massachusetts?

In general, June is the cheapest month to fly from Winnipeg to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $318. If you aren’t able to travel to Massachusetts during the month of June, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $320.

What is the cheapest day to depart on your flight to Massachusetts?

According to our data, Saturday is the cheapest day to fly to Massachusetts from Winnipeg. The lowest ticket price found for a Saturday departure recently was $369. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Winnipeg because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $618.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our data shows that the cheapest Winnipeg to Massachusetts flights are usually those with departure times in the morning. Our users have found flights to Massachusetts in the morning for as low as $493. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $618 on average. Flights to Massachusetts from Winnipeg at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

How far in advance should I book a flight to Massachusetts?

You are more likely to see cheaper flights to Massachusetts from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $406 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Winnipeg for as low as $242 on momondo.

Cheap Winnipeg to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Massachusetts

Direct flights	None

There are no direct flights from Winnipeg to Massachusetts. There are no popular flight routes from Winnipeg to Massachusetts.

Search flight deals

When did momondo last update prices for flights from Winnipeg Airport to Massachusetts?
Prices for flights from Winnipeg Airport to Massachusetts refresh daily.
How many operators does momondo search for flights from Winnipeg Airport to Massachusetts?
The number of operators available for flights from Winnipeg Airport to Massachusetts is 3 as of October 2025.
How old do you have to be to fly from Winnipeg Airport to Massachusetts?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Massachusetts.
What documentation or ID do you need to fly to Massachusetts?
The travel and health documents required for your trip to Massachusetts can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Winnipeg to Massachusetts

Compare and see reviews for airlines that fly from Winnipeg to Massachusetts with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $100	Free Cancellation	Rating 7.4 8,999 reviews	Search United Airlines flights
Delta	PriceFrom $241	Free Cancellation	Rating 7.9 7,996 reviews	Search Delta flights
Air Canada	PriceFrom $254	Free Cancellation	Rating 7.1 10,367 reviews	Search Air Canada flights

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Massachusetts?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Winnipeg to Massachusetts for you.

Can I find flights from Winnipeg to Massachusetts with flexible booking policies on momondo?

momondo does allow users to show only those flights to Massachusetts from Winnipeg which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Winnipeg to Massachusetts?

momondo helps you find the best flight between Winnipeg and Massachusetts by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Winnipeg to Massachusetts right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Massachusetts, momondo offers a useful price alert feature which will track prices for flights to Massachusetts from Winnipeg and alert you when they change.