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 65% 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?

WestJet, Delta, and Porter Airlines 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 August 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$ 215 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.

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

8h 15m1 stop Toronto Pearson Intl

10:05 a.m. - 3:19 p.m.BOS Boston Logan Intl-YWG Winnipeg

6h 14m1 stop Toronto Pearson Intl

C$ 383Porter Airlines

Fri, 2 Oct - Mon, 5 Oct

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

8h 15m1 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$ 435Porter Airlines

Fri, 2 Oct - Mon, 5 Oct

6:00 a.m. - 5:40 p.m.YWG Winnipeg-BOS Boston Logan Intl

10h 40m1 stop Calgary

6:30 p.m. - 12:15 p.m.BOS Boston Logan Intl-YWG Winnipeg

18h 45m1 stop Calgary

C$ 453WestJet

Sat, 26 Sep - Sat, 3 Oct

7:10 p.m. - 5:40 p.m.YWG Winnipeg-BOS Boston Logan Intl

21h 30m1 stop Calgary

6:30 p.m. - 11:10 a.m.BOS Boston Logan Intl-YWG Winnipeg

17h 40m1 stop Calgary

C$ 470WestJet

Fri, 9 Oct - Sun, 18 Oct

11:15 a.m. - 10:30 a.m.YWG Winnipeg-BOS Boston Logan Intl

22h 15m2 stops Montreal St Hubert Toronto Island

7:30 p.m. - 9:45 a.m.BOS Boston Logan Intl-YWG Winnipeg

15h 15m1 stop Toronto Pearson Intl

C$ 471Multiple Airlines

Fri, 25 Sep - Wed, 30 Sep

12:15 p.m. - 6:35 p.m.YWG Winnipeg-BOS Boston Logan Intl

5h 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$ 473Porter Airlines

Thu, 3 Sep - Sun, 6 Sep

2:05 p.m. - 10:40 p.m.YWG Winnipeg-BOS Boston Logan Intl

7h 35m1 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$ 493Air Canada

Thu, 1 Oct - Sun, 4 Oct

3:20 p.m. - 10:40 p.m.YWG Winnipeg-BOS Boston Logan Intl

6h 20m1 stop Toronto Pearson Intl

3:35 p.m. - 9:14 p.m.BOS Boston Logan Intl-YWG Winnipeg

6h 39m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 496Air Canada

Wed, 7 Oct - Wed, 21 Oct

7:00 a.m. - 12:54 a.m.YWG Winnipeg-BOS Boston Logan Intl

16h 54m1 stop Chicago O'Hare Intl

7:01 a.m. - 10:33 p.m.BOS Boston Logan Intl-YWG Winnipeg

16h 32m1 stop Chicago O'Hare Intl

C$ 584United Airlines

Sat, 10 Oct - Tue, 20 Oct

7:00 a.m. - 7:06 p.m.YWG Winnipeg-BOS Boston Logan Intl

11h 06m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

12:30 p.m. - 10:33 p.m.BOS Boston Logan Intl-YWG Winnipeg

11h 03m2 stops Newark Chicago O'Hare Intl

C$ 584United Airlines

Tue, 6 Oct - Wed, 21 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

12:46 p.m. - 11:58 p.m.YWG Winnipeg-BOS Boston Logan Intl

10h 12m1 stop Minneapolis St Paul

5:51 a.m. - 3:08 p.m.BOS Boston Logan Intl-YWG Winnipeg

10h 17m1 stop Minneapolis St Paul

C$ 933Delta

Mon, 17 Aug - Fri, 21 Aug

12:15 p.m. - 6:50 p.m.YWG Winnipeg-BOS Boston Logan Intl

5h 35m1 stop Toronto Pearson Intl

7:10 a.m. - 5:58 p.m.BOS Boston Logan Intl-YWG Winnipeg

11h 48m2 stops Toronto Island Ottawa

C$ 954Porter Airlines

Mon, 17 Aug - Fri, 21 Aug

7:45 p.m. - 9:53 a.m.YWG Winnipeg-BOS Boston Logan Intl

13h 08m1 stop Toronto Pearson Intl

10:40 a.m. - 3:14 p.m.BOS Boston Logan Intl-YWG Winnipeg

5h 34m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 1,057Air Canada

Mon, 17 Aug - Fri, 21 Aug

3:58 p.m. - 10:01 p.m.YWG Winnipeg-BOS Boston Logan Intl

5h 03m1 stop Minneapolis St Paul

3:00 p.m. - 11:30 p.m.BOS Boston Logan Intl-YWG Winnipeg

9h 30m1 stop Minneapolis St Paul

C$ 1,197Delta

Mon, 17 Aug - Fri, 21 Aug

9:20 a.m. - 8:55 p.m.YWG Winnipeg-BOS Boston Logan Intl

10h 35m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

7:10 a.m. - 5:58 p.m.BOS Boston Logan Intl-YWG Winnipeg

11h 48m2 stops Toronto Island Ottawa

C$ 1,207Porter Airlines

Mon, 17 Aug - Fri, 21 Aug

12:15 p.m. - 6:50 p.m.YWG Winnipeg-BOS Boston Logan Intl

5h 35m1 stop Toronto Pearson Intl

7:10 a.m. - 5:58 p.m.BOS Boston Logan Intl-YWG Winnipeg

11h 48m2 stops Toronto Island Ottawa

C$ 1,216Porter Airlines

Mon, 17 Aug - Fri, 21 Aug

12:46 p.m. - 11:58 p.m.YWG Winnipeg-BOS Boston Logan Intl

10h 12m1 stop Minneapolis St Paul

7:10 a.m. - 4:52 p.m.BOS Boston Logan Intl-YWG Winnipeg

10h 42m1 stop Minneapolis St Paul

C$ 1,221Delta

Mon, 17 Aug - Fri, 21 Aug

8:15 a.m. - 4:03 p.m.YWG Winnipeg-BOS Boston Logan Intl

6h 48m1 stop Toronto Pearson Intl

3:40 p.m. - 9:19 p.m.BOS Boston Logan Intl-YWG Winnipeg

6h 39m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 1,370Air Canada

Sat, 15 Aug - Mon, 17 Aug

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

22h 45m1 stop Toronto Pearson Intl

3:55 p.m. - 4:25 p.m.BOS Boston Logan Intl-YWG Winnipeg

25h 30m2 stops Ottawa Toronto Pearson Intl

C$ 1,529Multiple Airlines

Sat, 15 Aug - Mon, 17 Aug

7:00 a.m. - 7:19 p.m.YWG Winnipeg-BOS Boston Logan Intl

11h 19m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

2:28 p.m. - 10:33 p.m.BOS Boston Logan Intl-YWG Winnipeg

9h 05m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl

C$ 1,662United Airlines

Sat, 15 Aug - Mon, 17 Aug

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Air Canada flights from Winnipeg to Massachusetts

Our best Air Canada deals on Winnipeg to Massachusetts flight tickets

Air Canada

6 Sep

YWG5:00 a.m.Winnipeg

8h 41m

2 stops

BOS2:41 p.m.Boston Logan Intl

14 Sep

BOS6:00 a.m.Boston Logan Intl

6h 12m

1 stop

YWG11:12 a.m.Winnipeg

C$ 329

Air Canada

6 Sep

YWG7:55 a.m.Winnipeg

5h 46m

1 stop

BOS2:41 p.m.Boston Logan Intl

14 Sep

BOS6:00 a.m.Boston Logan Intl

6h 12m

1 stop

YWG11:12 a.m.Winnipeg

C$ 332

Air Canada

6 Sep

YWG5:00 a.m.Winnipeg

8h 41m

2 stops

BOS2:41 p.m.Boston Logan Intl

14 Sep

BOS5:50 a.m.Boston Logan Intl

9h 27m

2 stops

YWG2:17 p.m.Winnipeg

C$ 342

Porter Airlines flights from Winnipeg to Massachusetts

Our best Porter Airlines deals on Winnipeg to Massachusetts flight tickets

Porter Airlines

23 Sep

YWG9:20 a.m.Winnipeg

8h 15m

1 stop

BOS6:35 p.m.Boston Logan Intl

30 Sep

BOS10:05 a.m.Boston Logan Intl

6h 14m

1 stop

YWG3:19 p.m.Winnipeg

C$ 350

Porter Airlines

23 Sep

YWG9:20 a.m.Winnipeg

8h 15m

1 stop

BOS6:35 p.m.Boston Logan Intl

1 Oct

BOS10:05 a.m.Boston Logan Intl

6h 14m

1 stop

YWG3:19 p.m.Winnipeg

C$ 361

Porter Airlines

2 Oct

YWG9:20 a.m.Winnipeg

8h 15m

1 stop

BOS6:35 p.m.Boston Logan Intl

5 Oct

BOS10:05 a.m.Boston Logan Intl

6h 14m

1 stop

YWG3:19 p.m.Winnipeg

C$ 383

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 2/10

9:20 a.m.-6:35 p.m.

1 stop8h 15m

Boston Logan Intl

Mon 5/10

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

1 stop6h 14m

C$ 383

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 2/10

9:20 a.m.-6:35 p.m.

1 stop8h 15m

Boston Logan Intl

Mon 5/10

7:00 a.m.-5:58 p.m.

2 stops11h 58m

C$ 435

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 26/9

6:00 a.m.-5:40 p.m.

1 stop10h 40m

Boston Logan Intl

Sat 3/10

6:30 p.m.-12:15 p.m.

1 stop18h 45m

C$ 453

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 9/10

7:10 p.m.-5:40 p.m.

1 stop21h 30m

Boston Logan Intl

Sun 18/10

6:30 p.m.-11:10 a.m.

1 stop17h 40m

C$ 470

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 25/9

11:15 a.m.-10:30 a.m.

2 stops22h 15m

Boston Logan Intl

Wed 30/9

7:30 p.m.-9:45 a.m.

1 stop15h 15m

C$ 471

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 3/9

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

1 stop5h 20m

Boston Logan Intl

Sun 6/9

7:00 a.m.-5:58 p.m.

2 stops11h 58m

C$ 473

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 1/10

2:05 p.m.-10:40 p.m.

1 stop7h 35m

Boston Logan Intl

Sun 4/10

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

1 stop6h 12m

C$ 493

Quickest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 7/10

3:20 p.m.-10:40 p.m.

1 stop6h 20m

Boston Logan Intl

Wed 21/10

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

1 stop6h 39m

C$ 496

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 10/10

7:00 a.m.-12:54 a.m.

1 stop16h 54m

Boston Logan Intl

Tue 20/10

7:01 a.m.-10:33 p.m.

1 stop16h 32m

C$ 584

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 6/10

7:00 a.m.-7:06 p.m.

2 stops11h 06m

Boston Logan Intl

Wed 21/10

12:30 p.m.-10:33 p.m.

2 stops11h 03m

C$ 584

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$ 485, 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 June is also very affordable. Most momondo users find prices during this month for around C$ 527.

Can stopping save me money on Winnipeg to Massachusetts flights?

You could potentially save up to 35% 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 August 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$ 162	Free Cancellation	Rating 7.4 10,108 reviews	Search United Airlines flights
Porter Airlines	PriceFrom C$ 326	Free Cancellation	Rating 8.0 456 reviews	Search Porter Airlines flights
Air Canada	PriceFrom C$ 396	Free Cancellation	Rating 7.1 11,470 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.