What airlines fly to Massachusetts?

Air Canada, United Airlines and Porter Airlines 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 45% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 4 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

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

WestJet, United Airlines, and Air Canada are the most popular carriers operating from Winnipeg to Massachusetts

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 4 as of August 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.

$166 Cheap Flights from Winnipeg to Massachusetts in 2025

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Find the cheapest flights from Winnipeg to Massachusetts

Round-trip

One-way

Cheap round-trip flights

9:05 pm - 5:40 pmYWG-BOS

19h 35m1 stop

3:00 pm - 4:22 pmBOS-YWG

26h 22m2 stops

$335

Find Deal

Wed, Sep 17 - Wed, Sep 24

5:00 am - 11:29 amYWG-BOS

5h 29m1 stop

6:00 am - 10:40 amBOS-YWG

5h 40m1 stop

$340Air Canada

Find Deal

Wed, Sep 17 - Wed, Sep 24

5:38 pm - 11:59 pmYWG-BOS

5h 21m1 stop

12:00 pm - 11:27 pmBOS-YWG

12h 27m2 stops

$356Delta

Find Deal

Tue, Oct 7 - Wed, Oct 15

5:00 am - 11:27 amYWG-BOS

5h 27m1 stop

10:20 am - 3:00 pmBOS-YWG

5h 40m1 stop

$357Air Canada

Find Deal

Sat, Sep 27 - Wed, Oct 1

5:00 am - 5:55 pmYWG-BOS

11h 55m2 stops

6:00 am - 4:15 pmBOS-YWG

11h 15m2 stops

$363Air Canada

Find Deal

Tue, Oct 7 - Wed, Oct 15

6:30 pm - 9:30 amYWG-BOS

14h 00m2 stops

6:10 am - 12:30 amBOS-YWG

19h 20m3 stops

$371

Find Deal

Wed, Sep 17 - Wed, Sep 24

5:00 am - 4:22 pmYWG-BOS

10h 22m2 stops

6:00 am - 3:31 pmBOS-YWG

10h 31m2 stops

$446United Airlines

Find Deal

Sat, Sep 27 - Wed, Oct 1

9:00 am - 5:55 pmYWG-ALB

7h 55m1 stop

6:00 am - 4:58 pmALB-YWG

11h 58m2 stops

$707WestJet

Find Deal

Thu, Aug 21 - Thu, Aug 28

7:00 am - 9:48 pmYWG-ALB

13h 48m1 stop

1:19 pm - 10:33 pmALB-YWG

10h 14m1 stop

$746United Airlines

Find Deal

Thu, Aug 21 - Thu, Aug 28

6:30 am - 11:21 pmYWG-ALB

15h 51m2 stops

6:00 am - 4:58 pmALB-YWG

11h 58m2 stops

$772WestJet

Find Deal

Thu, Aug 21 - Thu, Aug 28

Air Canada flights from Winnipeg to Massachusetts

Our best Air Canada deals on Winnipeg to Massachusetts flight tickets

Air Canada

Sep 17

YWG5:00 amWinnipeg

5h 29m

1 stop

BOS11:29 amBoston Logan Intl

Sep 24

BOS6:00 amBoston Logan Intl

5h 40m

1 stop

YWG10:40 amWinnipeg

$340

Find similar

Air Canada

Sep 27

YWG5:00 amWinnipeg

5h 27m

1 stop

BOS11:27 amBoston Logan Intl

Oct 1

BOS10:20 amBoston Logan Intl

5h 40m

1 stop

YWG3:00 pmWinnipeg

$357

Find similar

Air Canada

Oct 7

YWG5:00 amWinnipeg

11h 55m

2 stops

BOS5:55 pmBoston Logan Intl

Oct 15

BOS6:00 amBoston Logan Intl

11h 15m

2 stops

YWG4:15 pmWinnipeg

$363

Find similar

United Airlines flights from Winnipeg to Massachusetts

Our best United Airlines deals on Winnipeg to Massachusetts flight tickets

United Airlines

Sep 27

YWG5:00 amWinnipeg

10h 22m

2 stops

BOS4:22 pmBoston Logan Intl

Oct 1

BOS6:00 amBoston Logan Intl

10h 31m

2 stops

YWG3:31 pmWinnipeg

$446

Find similar

United Airlines

Aug 21

YWG7:00 amWinnipeg

13h 48m

1 stop

ALB9:48 pmAlbany Intl

Aug 28

ALB1:19 pmAlbany Intl

10h 14m

1 stop

YWG10:33 pmWinnipeg

$746

Find similar

United Airlines

Aug 17

YWG4:25 pmWinnipeg

16h 58m

2 stops

ALB10:23 amAlbany Intl

Aug 24

ALB6:00 amAlbany Intl

32h 09m

2 stops

YWG1:09 pmWinnipeg

$780

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 9/17

9:05 pm-5:40 pm

1 stop19h 35m

Boston Logan Intl

Wed 9/24

3:00 pm-4:22 pm

2 stops26h 22m

$335

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 9/17

5:00 am-11:29 am

1 stop5h 29m

Boston Logan Intl

Wed 9/24

6:00 am-10:40 am

1 stop5h 40m

$340

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 10/7

5:38 pm-11:59 pm

1 stop5h 21m

Boston Logan Intl

Wed 10/15

12:00 pm-11:27 pm

2 stops12h 27m

$356

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 9/27

5:00 am-11:27 am

1 stop5h 27m

Boston Logan Intl

Wed 10/1

10:20 am-3:00 pm

1 stop5h 40m

$357

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 10/7

5:00 am-5:55 pm

2 stops11h 55m

Boston Logan Intl

Wed 10/15

6:00 am-4:15 pm

2 stops11h 15m

$363

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 9/17

6:30 pm-9:30 am

2 stops14h 00m

Boston Logan Intl

Wed 9/24

6:10 am-12:30 am

3 stops19h 20m

$371

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 9/27

5:00 am-4:22 pm

2 stops10h 22m

Boston Logan Intl

Wed 10/1

6:00 am-3:31 pm

2 stops10h 31m

$446

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Thu 8/21

9:00 am-5:55 pm

1 stop7h 55m

Albany Intl

Thu 8/28

6:00 am-4:58 pm

2 stops11h 58m

$707

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Thu 8/21

7:00 am-9:48 pm

1 stop13h 48m

Albany Intl

Thu 8/28

1:19 pm-10:33 pm

1 stop10h 14m

$746

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Thu 8/21

6:30 am-11:21 pm

2 stops15h 51m

Albany Intl

Thu 8/28

6:00 am-4:58 pm

2 stops11h 58m

$772

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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, October 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 $295. If you aren’t able to travel to Massachusetts during the month of October, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $325.

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 $399 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

Best Price Found	$166
Fastest flight time	5h 21m
Direct flights	None
Airports in Massachusetts	2 airports

The best one-way flight to Massachusetts from Winnipeg in the past 72 hours is $166. The best round-trip flight deal from Winnipeg to Massachusetts found on momondo in the last 72 hours is $335.

The fastest flight from Winnipeg to Massachusetts takes 5h 21m

There are no direct flights from Winnipeg to Massachusetts. Popular non-direct routes for this connection are Winnipeg Airport - Boston Logan Intl Airport and Winnipeg Airport - Albany Intl Airport.

There are 2 airports near Massachusetts: Boston Logan Intl (BOS), Albany Intl (ALB)

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 4 as of August 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 8,912 reviews	Search United Airlines flights
Delta	PriceFrom $241	Free Cancellation	Rating 8.0 7,987 reviews	Search Delta flights
Air Canada	PriceFrom $254	Free Cancellation	Rating 7.1 9,879 reviews	Search Air Canada flights
Porter Airlines	PriceFrom $267	Free Cancellation	Rating 8.0 321 reviews	Search Porter Airlines 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.