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 64% 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.

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

Delta is the most popular carrier 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 September 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$ 231 Cheap Flights from Winnipeg to Massachusetts in 2026/27

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.

2:00 p.m. - 11:24 p.m.YWG Winnipeg-BOS Boston Logan Intl

8h 24m1 stop Chicago O'Hare Intl

6:00 a.m. - 12:37 p.m.BOS Boston Logan Intl-YWG Winnipeg

7h 37m1 stop Chicago O'Hare Intl

C$ 393United Airlines

Wed, 21 Oct - Thu, 22 Oct

5:00 a.m. - 11:50 a.m.YWG Winnipeg-BOS Boston Logan Intl

5h 50m1 stop Toronto Pearson Intl

6:00 a.m. - 11:12 a.m.BOS Boston Logan Intl-YWG Winnipeg

6h 12m1 stop Toronto Pearson Intl

C$ 409Air Canada

Wed, 21 Oct - Thu, 22 Oct

11:40 a.m. - 9:32 p.m.YWG Winnipeg-BOS Boston Logan Intl

8h 52m2 stops Ottawa Toronto Island

1:15 p.m. - 6:10 p.m.BOS Boston Logan Intl-YWG Winnipeg

5h 55m1 stop Ottawa

C$ 413Porter Airlines

Thu, 29 Oct - Thu, 5 Nov

11:40 a.m. - 9:32 p.m.YWG Winnipeg-BOS Boston Logan Intl

8h 52m2 stops Ottawa Toronto Island

8:00 a.m. - 6:10 p.m.BOS Boston Logan Intl-YWG Winnipeg

11h 10m2 stops Toronto Island Ottawa

C$ 414Porter Airlines

Thu, 29 Oct - Thu, 5 Nov

7:10 p.m. - 9:55 a.m.YWG Winnipeg-BOS Boston Logan Intl

13h 45m1 stop Toronto Pearson Intl

5:05 p.m. - 11:47 p.m.BOS Boston Logan Intl-YWG Winnipeg

7h 42m1 stop Toronto Pearson Intl

C$ 424Air Canada

Fri, 16 Oct - Tue, 20 Oct

6:35 a.m. - 4:44 p.m.YWG Winnipeg-BOS Boston Logan Intl

9h 09m1 stop Minneapolis St Paul

2:59 p.m. - 11:33 p.m.BOS Boston Logan Intl-YWG Winnipeg

9h 34m1 stop Minneapolis St Paul

C$ 437Delta

Wed, 25 Nov - Mon, 30 Nov

5:32 p.m. - 11:44 p.m.YWG Winnipeg-BOS Boston Logan Intl

5h 12m1 stop Minneapolis St Paul

2:59 p.m. - 11:33 p.m.BOS Boston Logan Intl-YWG Winnipeg

9h 34m1 stop Minneapolis St Paul

C$ 450Delta

Wed, 25 Nov - Mon, 30 Nov

2:05 p.m. - 9:28 p.m.YWG Winnipeg-BOS Boston Logan Intl

6h 23m1 stop Montreal Pierre Elliott Trudeau Intl

10:25 a.m. - 4:38 p.m.BOS Boston Logan Intl-YWG Winnipeg

7h 13m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 826Air Canada

Wed, 25 Nov - Mon, 30 Nov

2:15 p.m. - 11:16 p.m.YWG Winnipeg-BOS Boston Logan Intl

8h 01m1 stop Chicago O'Hare Intl

6:00 a.m. - 11:39 a.m.BOS Boston Logan Intl-YWG Winnipeg

6h 39m1 stop Chicago O'Hare Intl

C$ 885United Airlines

Tue, 30 Mar - Wed, 7 Apr

2:15 p.m. - 11:16 p.m.YWG Winnipeg-BOS Boston Logan Intl

8h 01m1 stop Chicago O'Hare Intl

6:00 a.m. - 11:39 a.m.BOS Boston Logan Intl-YWG Winnipeg

6h 39m1 stop Chicago O'Hare Intl

C$ 918United Airlines

Tue, 30 Mar - Mon, 5 Apr

Cheap last-minute flights

Enter your travel dates to find the best prices.

9:20 a.m. - 6:35 p.m.YWG Winnipeg-BOS Boston Logan Intl

8h 15m1 stop Toronto Pearson Intl

10:05 a.m. - 3:20 p.m.BOS Boston Logan Intl-YWG Winnipeg

6h 15m1 stop Toronto Pearson Intl

C$ 894Porter Airlines

Fri, 2 Oct - Mon, 5 Oct

5:10 p.m. - 9:05 a.m.YWG Winnipeg-BOS Boston Logan Intl

14h 55m1 stop Toronto Pearson Intl

7:30 p.m. - 4:25 p.m.BOS Boston Logan Intl-YWG Winnipeg

21h 55m1 stop Toronto Pearson Intl

C$ 994Multiple Airlines

Sun, 4 Oct - Mon, 5 Oct

5:10 p.m. - 9:05 a.m.YWG Winnipeg-BOS Boston Logan Intl

14h 55m1 stop Toronto Pearson Intl

3:55 p.m. - 3:25 p.m.BOS Boston Logan Intl-YWG Winnipeg

24h 30m2 stops Ottawa Calgary

C$ 1,087Multiple Airlines

Sun, 4 Oct - Mon, 5 Oct

9:20 a.m. - 9:05 a.m.YWG Winnipeg-BOS Boston Logan Intl

22h 45m1 stop Toronto Pearson Intl

7:00 a.m. - 5:58 p.m.BOS Boston Logan Intl-YWG Winnipeg

11h 58m2 stops Toronto Island Ottawa

C$ 1,168Porter Airlines

Fri, 2 Oct - Mon, 5 Oct

4:15 p.m. - 9:05 a.m.YWG Winnipeg-BOS Boston Logan Intl

15h 50m2 stops Ottawa Toronto Pearson Intl

7:00 a.m. - 5:58 p.m.BOS Boston Logan Intl-YWG Winnipeg

11h 58m2 stops Toronto Island Ottawa

C$ 1,168Porter Airlines

Fri, 2 Oct - Mon, 5 Oct

9:20 a.m. - 9:05 a.m.YWG Winnipeg-BOS Boston Logan Intl

22h 45m1 stop Toronto Pearson Intl

7:30 p.m. - 3:20 p.m.BOS Boston Logan Intl-YWG Winnipeg

20h 50m1 stop Toronto Pearson Intl

C$ 1,220Porter Airlines

Fri, 2 Oct - Mon, 5 Oct

9:20 a.m. - 10:40 p.m.YWG Winnipeg-BOS Boston Logan Intl

12h 20m2 stops Toronto Pearson Intl New York LaGuardia

3:55 p.m. - 3:20 p.m.BOS Boston Logan Intl-YWG Winnipeg

24h 25m2 stops Ottawa Toronto Pearson Intl

C$ 1,230Porter Airlines

Sun, 4 Oct - Mon, 5 Oct

11:40 a.m. - 3:14 p.m.YWG Winnipeg-BOS Boston Logan Intl

26h 34m2 stops Ottawa Toronto Island

7:00 a.m. - 5:58 p.m.BOS Boston Logan Intl-YWG Winnipeg

11h 58m2 stops Toronto Island Ottawa

C$ 1,280Porter Airlines

Fri, 2 Oct - Mon, 5 Oct

8:45 p.m. - 9:05 a.m.YWG Winnipeg-BOS Boston Logan Intl

11h 20m1 stop Toronto Pearson Intl

7:00 a.m. - 5:58 p.m.BOS Boston Logan Intl-YWG Winnipeg

11h 58m2 stops Toronto Island Ottawa

C$ 1,282Porter Airlines

Fri, 2 Oct - Mon, 5 Oct

8:45 p.m. - 9:05 a.m.YWG Winnipeg-BOS Boston Logan Intl

11h 20m1 stop Toronto Pearson Intl

10:05 a.m. - 3:20 p.m.BOS Boston Logan Intl-YWG Winnipeg

6h 15m1 stop Toronto Pearson Intl

C$ 1,294Porter Airlines

Fri, 2 Oct - Mon, 5 Oct

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Air Canada flights from Winnipeg to Massachusetts

Our best Air Canada deals on Winnipeg to Massachusetts flight tickets

Air Canada

21 Oct

YWG5:00 a.m.Winnipeg

5h 50m

1 stop

BOS11:50 a.m.Boston Logan Intl

22 Oct

BOS6:00 a.m.Boston Logan Intl

6h 12m

1 stop

YWG11:12 a.m.Winnipeg

C$ 409

Air Canada

16 Oct

YWG7:10 p.m.Winnipeg

13h 45m

1 stop

BOS9:55 a.m.Boston Logan Intl

20 Oct

BOS5:05 p.m.Boston Logan Intl

7h 42m

1 stop

YWG11:47 p.m.Winnipeg

C$ 424

Porter Airlines flights from Winnipeg to Massachusetts

Our best Porter Airlines deals on Winnipeg to Massachusetts flight tickets

Porter Airlines

29 Oct

YWG11:40 a.m.Winnipeg

8h 52m

2 stops

BOS9:32 p.m.Boston Logan Intl

5 Nov

BOS1:15 p.m.Boston Logan Intl

5h 55m

1 stop

YWG6:10 p.m.Winnipeg

C$ 413

Porter Airlines

29 Oct

YWG11:40 a.m.Winnipeg

8h 52m

2 stops

BOS9:32 p.m.Boston Logan Intl

5 Nov

BOS8:00 a.m.Boston Logan Intl

11h 10m

2 stops

YWG6:10 p.m.Winnipeg

C$ 414

Porter Airlines

24 Nov

YWG11:40 a.m.Winnipeg

8h 52m

2 stops

BOS9:32 p.m.Boston Logan Intl

29 Nov

BOS8:00 a.m.Boston Logan Intl

11h 10m

2 stops

YWG6:10 p.m.Winnipeg

C$ 417

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 21/10

2:00 p.m.-11:24 p.m.

1 stop8h 24m

Boston Logan Intl

Thu 22/10

6:00 a.m.-12:37 p.m.

1 stop7h 37m

C$ 393

Quickest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 21/10

5:00 a.m.-11:50 a.m.

1 stop5h 50m

Boston Logan Intl

Thu 22/10

6:00 a.m.-11:12 a.m.

1 stop6h 12m

C$ 409

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 29/10

11:40 a.m.-9:32 p.m.

2 stops8h 52m

Boston Logan Intl

Thu 5/11

1:15 p.m.-6:10 p.m.

1 stop5h 55m

C$ 413

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 29/10

11:40 a.m.-9:32 p.m.

2 stops8h 52m

Boston Logan Intl

Thu 5/11

8:00 a.m.-6:10 p.m.

2 stops11h 10m

C$ 414

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 16/10

7:10 p.m.-9:55 a.m.

1 stop13h 45m

Boston Logan Intl

Tue 20/10

5:05 p.m.-11:47 p.m.

1 stop7h 42m

C$ 424

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 25/11

6:35 a.m.-4:44 p.m.

1 stop9h 09m

Boston Logan Intl

Mon 30/11

2:59 p.m.-11:33 p.m.

1 stop9h 34m

C$ 437

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 25/11

5:32 p.m.-11:44 p.m.

1 stop5h 12m

Boston Logan Intl

Mon 30/11

2:59 p.m.-11:33 p.m.

1 stop9h 34m

C$ 450

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 25/11

2:05 p.m.-9:28 p.m.

1 stop6h 23m

Boston Logan Intl

Mon 30/11

10:25 a.m.-4:38 p.m.

1 stop7h 13m

C$ 826

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 30/3

2:15 p.m.-11:16 p.m.

1 stop8h 01m

Boston Logan Intl

Wed 7/4

6:00 a.m.-11:39 a.m.

1 stop6h 39m

C$ 885

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 30/3

2:15 p.m.-11:16 p.m.

1 stop8h 01m

Boston Logan Intl

Mon 5/4

6:00 a.m.-11:39 a.m.

1 stop6h 39m

C$ 918

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 August. Flight prices, which tend to average around C$ 494, are often lower during this time because this is during the off-season. If you are unable to visit Massachusetts during the month of August, then departing from Winnipeg during the month September is also very affordable. Most momondo users find prices during this month for around C$ 506.

Can stopping save me money on Winnipeg to Massachusetts flights?

You could potentially save up to 54% 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

Best price found	C$ 231
Fastest flight time	8h 35m
Direct flights	None

The best one-way flight to Massachusetts from Winnipeg in the past 72 hours is C$ 231. The best round-trip flight deal from Winnipeg to Massachusetts found on momondo in the last 72 hours is C$ 393.

The fastest flight from Winnipeg to Massachusetts takes 8h 35m

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 September 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$ 165	Free Cancellation	Rating 7.4 10,260 reviews	Search United Airlines flights
Porter Airlines	PriceFrom C$ 332	Free Cancellation	Rating 8.0 465 reviews	Search Porter Airlines flights
Air Canada	PriceFrom C$ 404	Free Cancellation	Rating 7.1 11,706 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.