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

WestJet is the most popular carrier operating from Massachusetts to Winnipeg

What airlines fly to Winnipeg?

Air Canada, Porter Airlines and Delta are the top three most popular airlines that fly to Winnipeg from Massachusetts according to our data. Air Canada is the first choice among our users, with 62% of people opting to fly with this airline when traveling to Winnipeg. Keep in mind that there are 4 different airlines that fly to Winnipeg on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Massachusetts to Winnipeg Airport?

Prices for flights from Massachusetts to Winnipeg Airport are refreshed on a daily basis.

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

The number of operators available for flights from Massachusetts to Winnipeg Airport is 4 as of August 2026.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Massachusetts to Winnipeg Airport.

What documentation or ID do you need to fly to Winnipeg Airport?

The required travel and health documents for your Winnipeg Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Winnipeg Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$135 Cheap Flights from Massachusetts to Winnipeg in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Massachusetts to Winnipeg

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:05 am - 5:15 pmBOS Boston Logan Intl-YWG Winnipeg

8h 10m1 stop Toronto Pearson Intl

11:15 am - 10:30 amYWG Winnipeg-BOS Boston Logan Intl

22h 15m2 stops Montreal St Hubert Toronto Island

$318Multiple Airlines

Thu, Sep 17 - Mon, Sep 21

10:05 am - 5:15 pmBOS Boston Logan Intl-YWG Winnipeg

8h 10m1 stop Toronto Pearson Intl

7:45 am - 6:35 pmYWG Winnipeg-BOS Boston Logan Intl

9h 50m1 stop Toronto Pearson Intl

$330Multiple Airlines

Thu, Sep 17 - Mon, Sep 21

10:05 am - 3:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 14m1 stop Toronto Pearson Intl

9:20 am - 6:35 pmYWG Winnipeg-BOS Boston Logan Intl

8h 15m1 stop Toronto Pearson Intl

$331Porter Airlines

Sat, Sep 26 - Wed, Sep 30

10:05 am - 3:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 14m1 stop Toronto Pearson Intl

12:15 pm - 6:35 pmYWG Winnipeg-BOS Boston Logan Intl

5h 20m1 stop Toronto Pearson Intl

$336Porter Airlines

Mon, Aug 31 - Wed, Sep 2

10:05 am - 5:15 pmBOS Boston Logan Intl-YWG Winnipeg

8h 10m1 stop Toronto Pearson Intl

11:15 am - 10:30 amYWG Winnipeg-BOS Boston Logan Intl

22h 15m2 stops Montreal St Hubert Toronto Island

$336Multiple Airlines

Thu, Sep 17 - Mon, Sep 21

10:05 am - 3:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 14m1 stop Toronto Pearson Intl

12:15 pm - 6:35 pmYWG Winnipeg-BOS Boston Logan Intl

5h 20m1 stop Toronto Pearson Intl

$338Porter Airlines

Mon, Aug 31 - Wed, Sep 2

10:35 am - 4:38 pmBOS Boston Logan Intl-YWG Winnipeg

7h 03m1 stop Montreal Pierre Elliott Trudeau Intl

8:05 am - 2:53 pmYWG Winnipeg-BOS Boston Logan Intl

5h 48m1 stop Montreal Pierre Elliott Trudeau Intl

$344Air Canada

Fri, Nov 6 - Fri, Nov 13

5:00 pm - 11:07 pmBOS Boston Logan Intl-YWG Winnipeg

7h 07m1 stop Toronto Pearson Intl

8:10 am - 2:41 pmYWG Winnipeg-BOS Boston Logan Intl

5h 31m1 stop Montreal Pierre Elliott Trudeau Intl

$349Air Canada

Fri, Oct 2 - Sun, Oct 4

2:28 pm - 10:33 pmBOS Boston Logan Intl-YWG Winnipeg

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

7:00 am - 7:28 pmYWG Winnipeg-BOS Boston Logan Intl

11h 28m2 stops Chicago O'Hare Intl Newark

$430United Airlines

Sat, Aug 29 - Sat, Sep 5

8:15 am - 8:57 pmBOS Boston Logan Intl-YWG Winnipeg

13h 42m2 stops Los Angeles Denver Intl

2:00 pm - 9:59 pmYWG Winnipeg-BOS Boston Logan Intl

6h 59m1 stop Chicago O'Hare Intl

$510United Airlines

Tue, Sep 1 - Thu, Sep 10

Cheap last minute flights

Enter your travel dates to find the best prices.

10:05 am - 3:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 14m1 stop Toronto Pearson Intl

12:15 pm - 6:50 pmYWG Winnipeg-BOS Boston Logan Intl

5h 35m1 stop Toronto Pearson Intl

$581Porter Airlines

Thu, Aug 13 - Sun, Aug 16

7:45 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

13h 55m1 stop Toronto Pearson Intl

8:10 pm - 3:15 pmYWG Winnipeg-BOS Boston Logan Intl

18h 05m1 stop Toronto Pearson Intl

$581Multiple Airlines

Sun, Aug 16 - Mon, Aug 24

3:55 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

17h 45m2 stops Ottawa Toronto Pearson Intl

8:10 pm - 10:30 amYWG Winnipeg-BOS Boston Logan Intl

13h 20m1 stop Toronto Pearson Intl

$618Multiple Airlines

Sun, Aug 16 - Mon, Aug 24

3:55 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

17h 45m2 stops Ottawa Toronto Pearson Intl

9:25 am - 8:55 pmYWG Winnipeg-BOS Boston Logan Intl

10h 30m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$666Multiple Airlines

Sun, Aug 16 - Mon, Aug 24

10:05 am - 3:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 14m1 stop Toronto Pearson Intl

12:15 pm - 6:50 pmYWG Winnipeg-BOS Boston Logan Intl

5h 35m1 stop Toronto Pearson Intl

$671Porter Airlines

Sun, Aug 16 - Mon, Aug 24

10:05 am - 4:25 pmBOS Boston Logan Intl-YWG Winnipeg

7h 20m1 stop Toronto Pearson Intl

9:25 am - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

22h 40m1 stop Toronto Pearson Intl

$789Multiple Airlines

Thu, Aug 13 - Sun, Aug 16

10:05 am - 10:20 amBOS Boston Logan Intl-YWG Winnipeg

25h 15m2 stops Toronto Pearson Intl Montreal St Hubert

9:25 am - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

22h 40m1 stop Toronto Pearson Intl

$856Multiple Airlines

Thu, Aug 13 - Sun, Aug 16

4:45 pm - 9:45 amBOS Boston Logan Intl-YWG Winnipeg

18h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

4:15 pm - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

15h 50m2 stops Ottawa Toronto Pearson Intl

$898Multiple Airlines

Thu, Aug 13 - Sun, Aug 16

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Porter Airlines flights from Massachusetts to Winnipeg

Our best Porter Airlines deals on Massachusetts to Winnipeg flight tickets

Porter Airlines

Sep 26

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Sep 30

YWG9:20 amWinnipeg

8h 15m

1 stop

BOS6:35 pmBoston Logan Intl

$331

Porter Airlines

Aug 31

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Sep 2

YWG12:15 pmWinnipeg

5h 20m

1 stop

BOS6:35 pmBoston Logan Intl

$336

Porter Airlines

Aug 31

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Sep 2

YWG12:15 pmWinnipeg

5h 20m

1 stop

BOS6:35 pmBoston Logan Intl

$338

Air Canada flights from Massachusetts to Winnipeg

Our best Air Canada deals on Massachusetts to Winnipeg flight tickets

Air Canada

Nov 6

BOS10:35 amBoston Logan Intl

7h 03m

1 stop

YWG4:38 pmWinnipeg

Nov 13

YWG8:05 amWinnipeg

5h 48m

1 stop

BOS2:53 pmBoston Logan Intl

$344

Air Canada

Aug 29

BOS10:50 amBoston Logan Intl

6h 30m

1 stop

YWG4:20 pmWinnipeg

Sep 5

YWG10:55 amWinnipeg

6h 12m

1 stop

BOS6:07 pmBoston Logan Intl

$349

Air Canada

Aug 28

BOS6:00 amBoston Logan Intl

6h 15m

1 stop

YWG11:15 amWinnipeg

Aug 30

YWG5:00 amWinnipeg

5h 52m

1 stop

BOS11:52 amBoston Logan Intl

$354

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 9/17

10:05 am-5:15 pm

1 stop8h 10m

Winnipeg

Mon 9/21

11:15 am-10:30 am

2 stops22h 15m

$318

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 9/17

10:05 am-5:15 pm

1 stop8h 10m

Winnipeg

Mon 9/21

7:45 am-6:35 pm

1 stop9h 50m

$330

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 9/26

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Wed 9/30

9:20 am-6:35 pm

1 stop8h 15m

$331

Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 8/31

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Wed 9/2

12:15 pm-6:35 pm

1 stop5h 20m

$336

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 9/17

10:05 am-5:15 pm

1 stop8h 10m

Winnipeg

Mon 9/21

11:15 am-10:30 am

2 stops22h 15m

$336

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 8/31

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Wed 9/2

12:15 pm-6:35 pm

1 stop5h 20m

$338

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 11/6

10:35 am-4:38 pm

1 stop7h 03m

Winnipeg

Fri 11/13

8:05 am-2:53 pm

1 stop5h 48m

$344

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 10/2

5:00 pm-11:07 pm

1 stop7h 07m

Winnipeg

Sun 10/4

8:10 am-2:41 pm

1 stop5h 31m

$349

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 8/29

2:28 pm-10:33 pm

2 stops9h 05m

Winnipeg

Sat 9/5

7:00 am-7:28 pm

2 stops11h 28m

$430

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 9/1

8:15 am-8:57 pm

2 stops13h 42m

Winnipeg

Thu 9/10

2:00 pm-9:59 pm

1 stop6h 59m

$510

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 Massachusetts to Winnipeg

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 Winnipeg?

In general, May is the cheapest month to fly from Massachusetts to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $517. If you’re not able to fly to Winnipeg in May, then October is your next best option. Flight prices from Massachusetts to Winnipeg during October average around $519.

Cheap Massachusetts to Winnipeg flight deals and tips

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

Fastest flight time	5h 55m
Direct flights	None

The fastest flight from Massachusetts to Winnipeg takes 5h 55m

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

Search flight deals

Frequently asked questions about flying from Massachusetts to Winnipeg

When did momondo last update prices for flights from Massachusetts to Winnipeg Airport?
Prices for flights from Massachusetts to Winnipeg Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Massachusetts to Winnipeg Airport?
The number of operators available for flights from Massachusetts to Winnipeg Airport is 4 as of August 2026.
How old do you have to be to fly from Massachusetts to Winnipeg Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Massachusetts to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The required travel and health documents for your Winnipeg Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Winnipeg Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Massachusetts to Winnipeg

Compare and see reviews for airlines that fly from Massachusetts to Winnipeg with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $111	Free Cancellation	Rating 7.4 10,104 reviews	Search United Airlines flights
Air Canada	PriceFrom $204	Free Cancellation	Rating 7.1 11,462 reviews	Search Air Canada flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.8 8,505 reviews	Search Delta flights
Porter Airlines	PriceFrom $352	Free Cancellation	Rating 8.0 454 reviews	Search Porter Airlines flights

Selkirk

Portage la Prairie

Morden

Why use momondo?

Why should I use momondo to find a flight deal from Massachusetts to Winnipeg?

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 Massachusetts to Winnipeg for you.

Can I find flights from Massachusetts to Winnipeg with flexible booking policies on momondo?

Yes. All flights to Winnipeg from Massachusetts on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Massachusetts to Winnipeg.

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

Yes. momondo can track prices for Massachusetts to Winnipeg flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.