Which 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 51% of people opting to fly with this airline when travelling 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?

United Airlines, Air Canada, and WestJet 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 are refreshed on a daily basis.

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

As of March 2026, there are 4 operators available to choose from for flights from Winnipeg Airport to Massachusetts.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 you'll need for your trip to Massachusetts may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Massachusetts. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

C$ 249 Cheap Flights from Winnipeg to Massachusetts in 2026

1 adult

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Find the cheapest flights from Winnipeg to Massachusetts

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:20 a.m. - 5:35 p.m.

YWG

BOS

7h 15m

1 stop

10:05 a.m. - 3:19 p.m.

BOS

YWG

6h 14m

1 stop

C$ 393Porter Airlines

Tue, 19 May - Tue, 26 May

9:20 a.m. - 5:35 p.m.

YWG

BOS

7h 15m

1 stop

7:10 a.m. - 5:58 p.m.

BOS

YWG

11h 48m

2 stops

C$ 413Porter Airlines

Tue, 19 May - Tue, 26 May

5:10 a.m. - 11:46 a.m.

YWG

BOS

5h 36m

1 stop

5:10 a.m. - 11:08 a.m.

BOS

YWG

6h 58m

1 stop

C$ 431Air Canada

Sun, 10 May - Sat, 23 May

6:30 a.m. - 6:07 p.m.

YWG

BOS

10h 37m

2 stops

5:10 a.m. - 11:08 a.m.

BOS

YWG

6h 58m

1 stop

C$ 432Air Canada

Fri, 1 May - Tue, 5 May

9:20 a.m. - 5:35 p.m.

YWG

BOS

7h 15m

1 stop

7:10 a.m. - 5:58 p.m.

BOS

YWG

11h 48m

2 stops

C$ 437Porter Airlines

Thu, 18 Jun - Sun, 21 Jun

9:20 a.m. - 8:55 p.m.

YWG

BOS

10h 35m

2 stops

7:10 a.m. - 5:58 p.m.

BOS

YWG

11h 48m

2 stops

C$ 441Porter Airlines

Tue, 19 May - Tue, 26 May

7:00 a.m. - 3:26 p.m.

YWG

ALB

7h 26m

1 stop

6:10 a.m. - 11:52 a.m.

ALB

YWG

6h 42m

1 stop

C$ 487United Airlines

Sun, 24 May - Thu, 28 May

8:45 a.m. - 9:19 p.m.

YWG

ALB

11h 34m

2 stops

7:33 p.m. - 11:52 a.m.

ALB

YWG

17h 19m

2 stops

C$ 497United Airlines

Sat, 18 Apr - Wed, 22 Apr

6:15 a.m. - 11:06 p.m.

YWG

ALB

15h 51m

2 stops

1:15 p.m. - 12:55 a.m.

ALB

YWG

12h 40m

2 stops

C$ 566WestJet

Sat, 11 Jul - Fri, 4 Sep

10:45 a.m. - 11:06 p.m.

YWG

ALB

11h 21m

2 stops

6:00 a.m. - 12:55 a.m.

ALB

YWG

19h 55m

2 stops

C$ 569WestJet

Sat, 11 Jul - Fri, 4 Sep

Air Canada flights from Winnipeg to Massachusetts

Our best Air Canada deals on Winnipeg to Massachusetts flight tickets

Air Canada

10 May

YWG5:10 a.m.Winnipeg

5h 36m

1 stop

BOS11:46 a.m.Boston Logan Intl

23 May

BOS5:10 a.m.Boston Logan Intl

6h 58m

1 stop

YWG11:08 a.m.Winnipeg

C$ 431

Air Canada

1 May

YWG6:30 a.m.Winnipeg

10h 37m

2 stops

BOS6:07 p.m.Boston Logan Intl

5 May

BOS5:10 a.m.Boston Logan Intl

6h 58m

1 stop

YWG11:08 a.m.Winnipeg

C$ 432

Air Canada

1 May

YWG5:10 a.m.Winnipeg

8h 37m

2 stops

BOS2:47 p.m.Boston Logan Intl

5 May

BOS5:10 a.m.Boston Logan Intl

6h 58m

1 stop

YWG11:08 a.m.Winnipeg

C$ 442

United Airlines flights from Winnipeg to Massachusetts

Our best United Airlines deals on Winnipeg to Massachusetts flight tickets

United Airlines

18 Apr

YWG8:45 a.m.Winnipeg

24h 28m

2 stops

ALB10:13 a.m.Albany Intl

22 Apr

ALB7:33 p.m.Albany Intl

17h 19m

2 stops

YWG11:52 a.m.Winnipeg

C$ 453

United Airlines

18 Apr

YWG8:45 a.m.Winnipeg

11h 34m

2 stops

ALB9:19 p.m.Albany Intl

22 Apr

ALB7:33 p.m.Albany Intl

17h 19m

2 stops

YWG11:52 a.m.Winnipeg

C$ 497

United Airlines

18 Apr

YWG8:45 a.m.Winnipeg

11h 34m

2 stops

ALB9:19 p.m.Albany Intl

22 Apr

ALB6:05 a.m.Albany Intl

6h 47m

1 stop

YWG11:52 a.m.Winnipeg

C$ 506

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 19/5

9:20 a.m.-5:35 p.m.

1 stop7h 15m

Boston Logan Intl

Tue 26/5

10:05 a.m.-3:19 p.m.

1 stop6h 14m

C$ 393

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 19/5

9:20 a.m.-5:35 p.m.

1 stop7h 15m

Boston Logan Intl

Tue 26/5

7:10 a.m.-5:58 p.m.

2 stops11h 48m

C$ 413

Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 10/5

5:10 a.m.-11:46 a.m.

1 stop5h 36m

Boston Logan Intl

Sat 23/5

5:10 a.m.-11:08 a.m.

1 stop6h 58m

C$ 431

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 1/5

6:30 a.m.-6:07 p.m.

2 stops10h 37m

Boston Logan Intl

Tue 5/5

5:10 a.m.-11:08 a.m.

1 stop6h 58m

C$ 432

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 18/6

9:20 a.m.-5:35 p.m.

1 stop7h 15m

Boston Logan Intl

Sun 21/6

7:10 a.m.-5:58 p.m.

2 stops11h 48m

C$ 436

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 19/5

9:20 a.m.-8:55 p.m.

2 stops10h 35m

Boston Logan Intl

Tue 26/5

7:10 a.m.-5:58 p.m.

2 stops11h 48m

C$ 441

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sun 24/5

7:00 a.m.-3:26 p.m.

1 stop7h 26m

Albany Intl

Thu 28/5

6:10 a.m.-11:52 a.m.

1 stop6h 42m

C$ 487

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 18/4

8:45 a.m.-9:19 p.m.

2 stops11h 34m

Albany Intl

Wed 22/4

7:33 p.m.-11:52 a.m.

2 stops17h 19m

C$ 497

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 11/7

6:15 a.m.-11:06 p.m.

2 stops15h 51m

Albany Intl

Fri 4/9

1:15 p.m.-12:55 a.m.

2 stops12h 40m

C$ 566

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 11/7

10:45 a.m.-11:06 p.m.

2 stops11h 21m

Albany Intl

Fri 4/9

6:00 a.m.-12:55 a.m.

2 stops19h 55m

C$ 569

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?

The cheapest month to fly to Massachusetts from Winnipeg is in June. Flight prices, which tend to average around C$ 410, are often lower during this time because this is during the off-season. If you are unable to visit Massachusetts during the month of June, then departing from Winnipeg during the month August is also very affordable. Most momondo users find prices during this month for around C$ 454.

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 C$ 644 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 C$ 337 on momondo.

Can stopping save me money on Winnipeg to Massachusetts flights?

You could potentially save up to 34% on your flight if you consider stops on a Winnipeg to Massachusetts flight.

Cheap Winnipeg to Massachusetts flight deals and tips

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

Fastest flight time	5h 15m
Direct flights	None

The fastest flight from Winnipeg to Massachusetts takes 5h 15m

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 are refreshed on a daily basis.
How many operators does momondo search for flights from Winnipeg Airport to Massachusetts?
As of March 2026, there are 4 operators available to choose from for flights from Winnipeg Airport to Massachusetts.
How old do you have to be to fly from Winnipeg Airport to Massachusetts?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 you'll need for your trip to Massachusetts may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Massachusetts. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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 C$ 174	Free Cancellation	Rating 7.4 9,424 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 315	Free Cancellation	Rating 7.1 10,800 reviews	Search Air Canada flights
Porter Airlines	PriceFrom C$ 342	Free Cancellation	Rating 8.0 423 reviews	Search Porter Airlines flights
WestJet	PriceFrom C$ 469	Free Cancellation	Rating 7.2 3,295 reviews	Search WestJet 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?

Yes. momondo allows you to filter the results for Winnipeg to Massachusetts flights to just show those with flexible booking policies.

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

Once you have performed a search for Winnipeg to Massachusetts flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Massachusetts from Winnipeg are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.