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

Porter Airlines and Air Canada are the most popular carriers operating from Winnipeg to Massachusetts

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 43% 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.

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 May 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$ 241 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.

11:40 a.m. - 7:05 p.m.

YWG

BOS

6h 25m

1 stop

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

BOS

YWG

6h 14m

1 stop

C$ 378Porter Airlines

Wed, 3 Jun - Wed, 10 Jun

8:00 a.m. - 7:11 p.m.

YWG

BOS

10h 11m

1 stop

6:00 p.m. - 11:34 p.m.

BOS

YWG

6h 34m

1 stop

C$ 382Delta

Sat, 17 Oct - Wed, 21 Oct

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$ 400Porter Airlines

Tue, 21 Jul - Wed, 29 Jul

12:20 p.m. - 9:27 p.m.

YWG

BOS

8h 07m

2 stops

10:50 a.m. - 4:17 p.m.

BOS

YWG

6h 27m

1 stop

C$ 403Air Canada

Sat, 17 Oct - Wed, 21 Oct

11:40 a.m. - 7:05 p.m.

YWG

BOS

6h 25m

1 stop

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

BOS

YWG

6h 14m

1 stop

C$ 404Porter Airlines

Wed, 17 Jun - Fri, 26 Jun

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$ 407Porter Airlines

Tue, 4 Aug - Thu, 6 Aug

7:00 a.m. - 11:21 p.m.

YWG

ALB

15h 21m

2 stops

6:05 a.m. - 12:55 a.m.

ALB

YWG

19h 50m

2 stops

C$ 534WestJet

Tue, 7 Jul - Tue, 21 Jul

6:15 a.m. - 11:21 p.m.

YWG

ALB

16h 06m

2 stops

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

ALB

YWG

19h 55m

2 stops

C$ 545WestJet

Sat, 11 Jul - Fri, 4 Sep

2:05 p.m. - 9:39 a.m.

YWG

ALB

18h 34m

2 stops

4:30 p.m. - 10:24 p.m.

ALB

YWG

6h 54m

1 stop

C$ 601United Airlines

Tue, 22 Sep - Fri, 25 Sep

2:05 p.m. - 9:39 a.m.

YWG

ALB

18h 34m

2 stops

4:30 p.m. - 10:24 p.m.

ALB

YWG

6h 54m

1 stop

C$ 603United Airlines

Tue, 22 Sep - Fri, 25 Sep

Porter Airlines flights from Winnipeg to Massachusetts

Our best Porter Airlines deals on Winnipeg to Massachusetts flight tickets

Porter Airlines

3 Jun

YWG11:40 a.m.Winnipeg

6h 25m

1 stop

BOS7:05 p.m.Boston Logan Intl

10 Jun

BOS10:05 a.m.Boston Logan Intl

6h 14m

1 stop

YWG3:19 p.m.Winnipeg

C$ 378

Porter Airlines

21 Jul

YWG9:20 a.m.Winnipeg

7h 15m

1 stop

BOS5:35 p.m.Boston Logan Intl

29 Jul

BOS10:05 a.m.Boston Logan Intl

6h 14m

1 stop

YWG3:19 p.m.Winnipeg

C$ 400

Porter Airlines

4 Aug

YWG9:20 a.m.Winnipeg

7h 15m

1 stop

BOS5:35 p.m.Boston Logan Intl

8 Aug

BOS10:05 a.m.Boston Logan Intl

6h 14m

1 stop

YWG3:19 p.m.Winnipeg

C$ 407

Delta flights from Winnipeg to Massachusetts

Our best Delta deals on Winnipeg to Massachusetts flight tickets

Delta

17 Oct

YWG8:00 a.m.Winnipeg

10h 11m

1 stop

BOS7:11 p.m.Boston Logan Intl

21 Oct

BOS6:00 p.m.Boston Logan Intl

6h 34m

1 stop

YWG11:34 p.m.Winnipeg

C$ 382

Delta

17 Oct

YWG6:35 a.m.Winnipeg

9h 06m

1 stop

BOS4:41 p.m.Boston Logan Intl

21 Oct

BOS6:00 p.m.Boston Logan Intl

6h 34m

1 stop

YWG11:34 p.m.Winnipeg

C$ 421

Delta

29 May

YWG6:40 a.m.Winnipeg

9h 30m

1 stop

BOS5:10 p.m.Boston Logan Intl

3 Jun

BOS5:51 a.m.Boston Logan Intl

6h 03m

1 stop

YWG10:54 a.m.Winnipeg

C$ 463

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 3/6

11:40 a.m.-7:05 p.m.

1 stop6h 25m

Boston Logan Intl

Wed 10/6

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

1 stop6h 14m

C$ 378

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 17/10

8:00 a.m.-7:11 p.m.

1 stop10h 11m

Boston Logan Intl

Wed 21/10

6:00 p.m.-11:34 p.m.

1 stop6h 34m

C$ 382

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 21/7

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

1 stop7h 15m

Boston Logan Intl

Wed 29/7

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

1 stop6h 14m

C$ 400

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 17/10

12:20 p.m.-9:27 p.m.

2 stops8h 07m

Boston Logan Intl

Wed 21/10

10:50 a.m.-4:17 p.m.

1 stop6h 27m

C$ 403

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 17/6

11:40 a.m.-7:05 p.m.

1 stop6h 25m

Boston Logan Intl

Fri 26/6

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

1 stop6h 14m

C$ 404

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 4/8

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

1 stop7h 15m

Boston Logan Intl

Thu 6/8

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

1 stop6h 14m

C$ 407

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 7/7

7:00 a.m.-11:21 p.m.

2 stops15h 21m

Albany Intl

Tue 21/7

6:05 a.m.-12:55 a.m.

2 stops19h 50m

C$ 534

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 11/7

6:15 a.m.-11:21 p.m.

2 stops16h 06m

Albany Intl

Fri 4/9

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

2 stops19h 55m

C$ 545

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 22/9

2:05 p.m.-9:39 a.m.

2 stops18h 34m

Albany Intl

Fri 25/9

4:30 p.m.-10:24 p.m.

1 stop6h 54m

C$ 601

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 22/9

2:05 p.m.-9:39 a.m.

2 stops18h 34m

Albany Intl

Fri 25/9

4:30 p.m.-10:24 p.m.

1 stop6h 54m

C$ 603

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 May. Flight prices, which tend to average around C$ 137, are often lower during this time because this is during the off-season. If you are unable to visit Massachusetts during the month of May, then departing from Winnipeg during the month February is also very affordable. Most momondo users find prices during this month for around C$ 159.

Can stopping save me money on Winnipeg to Massachusetts flights?

You could potentially save up to 52% 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	6h 25m
Direct flights	None

The fastest flight from Winnipeg to Massachusetts takes 6h 25m

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

Search flight deals

Frequently asked questions about flying 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 May 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$ 214	Free Cancellation	Rating 7.4 9,711 reviews	Search United Airlines flights
Porter Airlines	PriceFrom C$ 321	Free Cancellation	Rating 8.0 436 reviews	Search Porter Airlines flights
Air Canada	PriceFrom C$ 389	Free Cancellation	Rating 7.1 11,029 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 470	Free Cancellation	Rating 7.2 3,334 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.