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 64% of people opting to fly with this airline when traveling to Winnipeg. Keep in mind that there are 3 different airlines that fly to Winnipeg on a routine basis, so you have a few additional options to choose from.

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

Delta, United Airlines, and Air Canada are the most popular carriers operating 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 3 as of March 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.

$117 Cheap Flights from Massachusetts to Winnipeg in 2026

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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 - 3:19 pm

BOS

YWG

6h 14m

1 stop

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$283Porter Airlines

Wed, May 20 - Tue, May 26

5:10 am - 11:08 am

BOS

YWG

6h 58m

1 stop

8:00 am - 2:47 pm

YWG

BOS

5h 47m

1 stop

$286Air Canada

Wed, May 20 - Sun, May 24

5:51 am - 10:54 am

BOS

YWG

6h 03m

1 stop

5:41 pm - 11:54 pm

YWG

BOS

5h 13m

1 stop

$289Delta

Tue, May 19 - Sun, May 24

5:10 am - 11:08 am

BOS

YWG

6h 58m

1 stop

3:15 pm - 10:39 pm

YWG

BOS

6h 24m

1 stop

$291Air Canada

Thu, May 28 - Mon, Jun 1

5:10 am - 11:08 am

BOS

YWG

6h 58m

1 stop

8:00 am - 2:47 pm

YWG

BOS

5h 47m

1 stop

$292Air Canada

Fri, May 8 - Sun, May 17

5:10 am - 11:08 am

BOS

YWG

6h 58m

1 stop

5:10 am - 2:47 pm

YWG

BOS

8h 37m

2 stops

$299Air Canada

Wed, May 20 - Sun, May 24

5:10 am - 11:08 am

BOS

YWG

6h 58m

1 stop

5:10 am - 2:47 pm

YWG

BOS

8h 37m

2 stops

$301Air Canada

Fri, May 8 - Sun, May 17

5:50 am - 2:18 pm

BOS

YWG

9h 28m

2 stops

5:10 am - 2:47 pm

YWG

BOS

8h 37m

2 stops

$308Air Canada

Thu, May 28 - Mon, Jun 1

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$313Porter Airlines

Tue, May 19 - Tue, May 26

5:10 am - 10:03 am

BOS

YWG

5h 53m

1 stop

7:20 pm - 9:54 am

YWG

BOS

13h 34m

1 stop

$315Air Canada

Fri, May 8 - Fri, May 15

Porter Airlines flights from Massachusetts to Winnipeg

Our best Porter Airlines deals on Massachusetts to Winnipeg flight tickets

Porter Airlines

May 20

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

May 26

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$283

Porter Airlines

May 19

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

May 26

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$313

Porter Airlines

Jun 23

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Jun 30

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$324

Air Canada flights from Massachusetts to Winnipeg

Our best Air Canada deals on Massachusetts to Winnipeg flight tickets

Air Canada

May 20

BOS5:10 amBoston Logan Intl

6h 58m

1 stop

YWG11:08 amWinnipeg

May 24

YWG8:00 amWinnipeg

5h 47m

1 stop

BOS2:47 pmBoston Logan Intl

$286

Air Canada

May 28

BOS5:10 amBoston Logan Intl

6h 58m

1 stop

YWG11:08 amWinnipeg

Jun 1

YWG3:15 pmWinnipeg

6h 24m

1 stop

BOS10:39 pmBoston Logan Intl

$291

Air Canada

May 8

BOS5:10 amBoston Logan Intl

6h 58m

1 stop

YWG11:08 amWinnipeg

May 17

YWG8:00 amWinnipeg

5h 47m

1 stop

BOS2:47 pmBoston Logan Intl

$292

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/20

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Tue 5/26

9:20 am-5:35 pm

1 stop7h 15m

$283

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/20

5:10 am-11:08 am

1 stop6h 58m

Winnipeg

Sun 5/24

8:00 am-2:47 pm

1 stop5h 47m

$286

Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 5/19

5:51 am-10:54 am

1 stop6h 03m

Winnipeg

Sun 5/24

5:41 pm-11:54 pm

1 stop5h 13m

$289

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 5/28

5:10 am-11:08 am

1 stop6h 58m

Winnipeg

Mon 6/1

3:15 pm-10:39 pm

1 stop6h 24m

$291

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 5/8

5:10 am-11:08 am

1 stop6h 58m

Winnipeg

Sun 5/17

8:00 am-2:47 pm

1 stop5h 47m

$292

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/20

5:10 am-11:08 am

1 stop6h 58m

Winnipeg

Sun 5/24

5:10 am-2:47 pm

2 stops8h 37m

$299

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 5/8

5:10 am-11:08 am

1 stop6h 58m

Winnipeg

Sun 5/17

5:10 am-2:47 pm

2 stops8h 37m

$301

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 5/28

5:50 am-2:18 pm

2 stops9h 28m

Winnipeg

Mon 6/1

5:10 am-2:47 pm

2 stops8h 37m

$308

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 5/19

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Tue 5/26

9:20 am-5:35 pm

1 stop7h 15m

$313

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 5/8

5:10 am-10:03 am

1 stop5h 53m

Winnipeg

Fri 5/15

7:20 pm-9:54 am

1 stop13h 34m

$315

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 $256. If you’re not able to fly to Winnipeg in May, then August is your next best option. Flight prices from Massachusetts to Winnipeg during August average around $420.

How far in advance should I book a flight to Winnipeg?

You are more likely to see cheaper flights to Winnipeg from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Winnipeg for around $510 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Winnipeg from Massachusetts for as low as $373 on momondo.

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 34m
Direct flights	None

The fastest flight from Massachusetts to Winnipeg takes 5h 34m

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

Search flight deals

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 3 as of March 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
Delta	PriceFrom $131	Free Cancellation	Rating 7.9 8,326 reviews	Search Delta flights
United Airlines	PriceFrom $149	Free Cancellation	Rating 7.4 9,477 reviews	Search United Airlines flights
Air Canada	PriceFrom $194	Free Cancellation	Rating 7.1 10,840 reviews	Search Air Canada flights

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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.