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

Porter Airlines is the most popular carrier operating from Winnipeg to Massachusetts

Which airlines fly to Massachusetts?

Air Canada, Porter Airlines and United 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 66% of people opting to fly with this airline when travelling 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 are refreshed on a daily basis.

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

As of June 2026, there are 3 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$ 250 Cheap Flights from Winnipeg to Massachusetts in 2026

Discover deals from 900+ travel sites with momondo.

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.

12:15 p.m. - 6:35 p.m.

YWG

BOS

5h 20m

1 stop

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

BOS

YWG

6h 14m

1 stop

C$ 415Porter Airlines

Fri, 10 Jul - Thu, 16 Jul

8:10 a.m. - 2:41 p.m.

YWG

BOS

5h 31m

1 stop

3:35 p.m. - 9:14 p.m.

BOS

YWG

6h 39m

1 stop

C$ 437Air Canada

Mon, 14 Sep - Fri, 18 Sep

8:15 a.m. - 4:03 p.m.

YWG

BOS

6h 48m

1 stop

5:45 a.m. - 2:25 p.m.

BOS

YWG

9h 40m

2 stops

C$ 446Air Canada

Fri, 10 Jul - Thu, 16 Jul

5:00 a.m. - 2:41 p.m.

YWG

BOS

8h 41m

2 stops

5:45 a.m. - 2:25 p.m.

BOS

YWG

9h 40m

2 stops

C$ 449Air Canada

Fri, 10 Jul - Thu, 16 Jul

3:20 p.m. - 10:38 p.m.

YWG

BOS

6h 18m

1 stop

6:00 a.m. - 11:15 a.m.

BOS

YWG

6h 15m

1 stop

C$ 457Air Canada

Fri, 7 Aug - Sat, 15 Aug

3:20 p.m. - 10:38 p.m.

YWG

BOS

6h 18m

1 stop

6:00 a.m. - 11:15 a.m.

BOS

YWG

6h 15m

1 stop

C$ 464Air Canada

Mon, 13 Jul - Tue, 21 Jul

3:58 p.m. - 11:59 p.m.

YWG

BOS

7h 01m

1 stop

5:55 a.m. - 11:56 a.m.

BOS

YWG

7h 01m

1 stop

C$ 467Delta

Mon, 14 Sep - Fri, 18 Sep

7:00 a.m. - 9:36 p.m.

YWG

ALB

13h 36m

1 stop

6:00 a.m. - 10:33 p.m.

ALB

YWG

17h 33m

2 stops

C$ 717United Airlines

Tue, 11 Aug - Tue, 18 Aug

7:00 a.m. - 9:27 p.m.

YWG

ALB

13h 27m

1 stop

8:10 a.m. - 10:33 p.m.

ALB

YWG

15h 23m

1 stop

C$ 761United Airlines

Sat, 11 Jul - Fri, 4 Sep

7:00 a.m. - 9:27 p.m.

YWG

ALB

13h 27m

1 stop

8:10 a.m. - 10:33 p.m.

ALB

YWG

15h 23m

1 stop

C$ 762United Airlines

Sat, 11 Jul - Fri, 4 Sep

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United Airlines flights from Winnipeg to Massachusetts

Our best United Airlines deals on Winnipeg to Massachusetts flight tickets

United Airlines

13 Jul

YWG12:56 p.m.Winnipeg

11h 18m

1 stop

BOS1:14 a.m.Boston Logan Intl

14 Jul

BOS6:05 p.m.Boston Logan Intl

18h 47m

2 stops

YWG11:52 a.m.Winnipeg

C$ 486

United Airlines

25 Jul

YWG5:00 a.m.Winnipeg

17h 59m

2 stops

BOS11:59 p.m.Boston Logan Intl

1 Aug

BOS8:27 p.m.Boston Logan Intl

15h 48m

2 stops

YWG11:15 a.m.Winnipeg

C$ 613

United Airlines

7 Aug

YWG12:56 p.m.Winnipeg

19h 57m

2 stops

BOS9:53 a.m.Boston Logan Intl

13 Aug

BOS5:45 a.m.Boston Logan Intl

17h 48m

2 stops

YWG10:33 p.m.Winnipeg

C$ 693

Porter Airlines flights from Winnipeg to Massachusetts

Our best Porter Airlines deals on Winnipeg to Massachusetts flight tickets

Porter Airlines

10 Jul

YWG12:15 p.m.Winnipeg

5h 20m

1 stop

BOS6:35 p.m.Boston Logan Intl

16 Jul

BOS10:05 a.m.Boston Logan Intl

6h 14m

1 stop

YWG3:19 p.m.Winnipeg

C$ 415

Porter Airlines

7 Aug

YWG12:15 p.m.Winnipeg

5h 35m

1 stop

BOS6:50 p.m.Boston Logan Intl

12 Aug

BOS10:05 a.m.Boston Logan Intl

6h 14m

1 stop

YWG3:19 p.m.Winnipeg

C$ 497

Porter Airlines

7 Aug

YWG12:15 p.m.Winnipeg

5h 20m

1 stop

BOS6:35 p.m.Boston Logan Intl

12 Aug

BOS10:05 a.m.Boston Logan Intl

6h 14m

1 stop

YWG3:19 p.m.Winnipeg

C$ 500

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 10/7

12:15 p.m.-6:35 p.m.

1 stop5h 20m

Boston Logan Intl

Thu 16/7

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

1 stop6h 14m

C$ 415

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 14/9

8:10 a.m.-2:41 p.m.

1 stop5h 31m

Boston Logan Intl

Fri 18/9

3:35 p.m.-9:14 p.m.

1 stop6h 39m

C$ 437

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 10/7

8:15 a.m.-4:03 p.m.

1 stop6h 48m

Boston Logan Intl

Thu 16/7

5:45 a.m.-2:25 p.m.

2 stops9h 40m

C$ 446

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 10/7

5:00 a.m.-2:41 p.m.

2 stops8h 41m

Boston Logan Intl

Thu 16/7

5:45 a.m.-2:25 p.m.

2 stops9h 40m

C$ 449

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 7/8

3:20 p.m.-10:38 p.m.

1 stop6h 18m

Boston Logan Intl

Sat 15/8

6:00 a.m.-11:15 a.m.

1 stop6h 15m

C$ 457

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 13/7

3:20 p.m.-10:38 p.m.

1 stop6h 18m

Boston Logan Intl

Tue 21/7

6:00 a.m.-11:15 a.m.

1 stop6h 15m

C$ 464

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 14/9

3:58 p.m.-11:59 p.m.

1 stop7h 01m

Boston Logan Intl

Fri 18/9

5:55 a.m.-11:56 a.m.

1 stop7h 01m

C$ 467

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 11/8

7:00 a.m.-9:36 p.m.

1 stop13h 36m

Albany Intl

Tue 18/8

6:00 a.m.-10:33 p.m.

2 stops17h 33m

C$ 717

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 11/7

7:00 a.m.-9:27 p.m.

1 stop13h 27m

Albany Intl

Fri 4/9

8:10 a.m.-10:33 p.m.

1 stop15h 23m

C$ 761

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 11/7

7:00 a.m.-9:27 p.m.

1 stop13h 27m

Albany Intl

Fri 4/9

8:10 a.m.-10:33 p.m.

1 stop15h 23m

C$ 762

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 February. Flight prices, which tend to average around C$ 165, are often lower during this time because this is during the off-season. If you are unable to visit Massachusetts during the month of February, then departing from Winnipeg during the month July is also very affordable. Most momondo users find prices during this month for around C$ 180.

Can stopping save me money on Winnipeg to Massachusetts flights?

You could potentially save up to 48% 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 20m
Direct flights	None

The fastest flight from Winnipeg to Massachusetts takes 5h 20m

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 June 2026, there are 3 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$ 221	Free Cancellation	Rating 7.4 9,904 reviews	Search United Airlines flights
Porter Airlines	PriceFrom C$ 332	Free Cancellation	Rating 8.0 441 reviews	Search Porter Airlines flights
Air Canada	PriceFrom C$ 403	Free Cancellation	Rating 7.1 11,275 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?

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.