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

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

What airlines fly to Winnipeg?

Air Canada, Delta and United Airlines 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 65% 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 June 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.

$160 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 pm

BOS

YWG

8h 10m

1 stop

11:15 am - 9:05 am

YWG

BOS

20h 50m

2 stops

$336Multiple Airlines

Wed, Sep 16 - Wed, Sep 23

7:30 pm - 12:55 am

BOS

YWG

6h 25m

1 stop

6:05 pm - 9:05 am

YWG

BOS

14h 00m

1 stop

$342Multiple Airlines

Wed, Sep 16 - Wed, Sep 23

8:00 am - 6:10 pm

BOS

YWG

11h 10m

2 stops

7:05 pm - 12:32 pm

YWG

BOS

16h 27m

1 stop

$345Porter Airlines

Fri, Oct 30 - Mon, Nov 2

10:05 am - 5:15 pm

BOS

YWG

8h 10m

1 stop

11:15 am - 6:35 pm

YWG

BOS

30h 20m

2 stops

$349Multiple Airlines

Wed, Sep 23 - Wed, Sep 30

7:30 pm - 12:55 am

BOS

YWG

6h 25m

1 stop

11:15 am - 9:05 am

YWG

BOS

20h 50m

2 stops

$353Multiple Airlines

Fri, Aug 28 - Mon, Aug 31

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

12:15 pm - 6:35 pm

YWG

BOS

5h 20m

1 stop

$355Porter Airlines

Mon, Jul 13 - Mon, Jul 27

7:10 am - 5:58 pm

BOS

YWG

11h 48m

2 stops

12:15 pm - 6:35 pm

YWG

BOS

5h 20m

1 stop

$358Porter Airlines

Mon, Jul 13 - Mon, Jul 27

7:30 pm - 12:55 am

BOS

YWG

6h 25m

1 stop

6:05 pm - 9:05 am

YWG

BOS

14h 00m

1 stop

$360Multiple Airlines

Fri, Aug 28 - Mon, Aug 31

10:05 am - 5:15 pm

BOS

YWG

8h 10m

1 stop

8:50 pm - 6:35 pm

YWG

BOS

20h 45m

1 stop

$361Multiple Airlines

Wed, Sep 23 - Wed, Sep 30

8:25 pm - 8:40 am

BOS

YWG

13h 15m

1 stop

11:15 am - 10:29 am

YWG

BOS

22h 14m

2 stops

$366Multiple Airlines

Mon, Jul 13 - Mon, Jul 27

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Porter Airlines flights from Massachusetts to Winnipeg

Our best Porter Airlines deals on Massachusetts to Winnipeg flight tickets

Porter Airlines

Oct 30

BOS8:00 amBoston Logan Intl

11h 10m

2 stops

YWG6:10 pmWinnipeg

Nov 2

YWG7:05 pmWinnipeg

16h 27m

1 stop

BOS12:32 pmBoston Logan Intl

$345

Porter Airlines

Jul 13

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Jul 27

YWG12:15 pmWinnipeg

5h 20m

1 stop

BOS6:35 pmBoston Logan Intl

$355

Porter Airlines

Jul 13

BOS7:10 amBoston Logan Intl

11h 48m

2 stops

YWG5:58 pmWinnipeg

Jul 27

YWG12:15 pmWinnipeg

5h 20m

1 stop

BOS6:35 pmBoston Logan Intl

$358

United Airlines flights from Massachusetts to Winnipeg

Our best United Airlines deals on Massachusetts to Winnipeg flight tickets

United Airlines

Aug 18

BOS8:31 pmBoston Logan Intl

16h 21m

1 stop

YWG11:52 amWinnipeg

Aug 21

YWG2:00 pmWinnipeg

10h 11m

1 stop

BOS1:11 amBoston Logan Intl

$425

United Airlines

Jul 8

BOS12:35 pmBoston Logan Intl

11h 03m

2 stops

YWG10:38 pmWinnipeg

Jul 11

YWG7:00 amWinnipeg

14h 12m

2 stops

BOS10:12 pmBoston Logan Intl

$547

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/16

10:05 am-5:15 pm

1 stop8h 10m

Winnipeg

Wed 9/23

11:15 am-9:05 am

2 stops20h 50m

$336

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/16

7:30 pm-12:55 am

1 stop6h 25m

Winnipeg

Wed 9/23

6:05 pm-9:05 am

1 stop14h 00m

$342

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 10/30

8:00 am-6:10 pm

2 stops11h 10m

Winnipeg

Mon 11/2

7:05 pm-12:32 pm

1 stop16h 27m

$345

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/23

10:05 am-5:15 pm

1 stop8h 10m

Winnipeg

Wed 9/30

11:15 am-6:35 pm

2 stops30h 20m

$349

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 8/28

7:30 pm-12:55 am

1 stop6h 25m

Winnipeg

Mon 8/31

11:15 am-9:05 am

2 stops20h 50m

$353

Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 7/13

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Mon 7/27

12:15 pm-6:35 pm

1 stop5h 20m

$355

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 7/13

7:10 am-5:58 pm

2 stops11h 48m

Winnipeg

Mon 7/27

12:15 pm-6:35 pm

1 stop5h 20m

$358

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 8/28

7:30 pm-12:55 am

1 stop6h 25m

Winnipeg

Mon 8/31

6:05 pm-9:05 am

1 stop14h 00m

$360

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/23

10:05 am-5:15 pm

1 stop8h 10m

Winnipeg

Wed 9/30

8:50 pm-6:35 pm

1 stop20h 45m

$361

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 7/13

8:25 pm-8:40 am

1 stop13h 15m

Winnipeg

Mon 7/27

11:15 am-10:29 am

2 stops22h 14m

$366

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 $111. If you’re not able to fly to Winnipeg in May, then March is your next best option. Flight prices from Massachusetts to Winnipeg during March average around $113.

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	6h 25m
Direct flights	None

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

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 June 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 $149	Free Cancellation	Rating 7.4 9,901 reviews	Search United Airlines flights
Air Canada	PriceFrom $194	Free Cancellation	Rating 7.1 11,269 reviews	Search Air Canada flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.8 8,455 reviews	Search Delta flights
Porter Airlines	PriceFrom $293	Free Cancellation	Rating 8.0 441 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.