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 4 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?

WestJet, Air Canada, and United Airlines 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 4 as of August 2025.

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.

$138 Cheap Flights from Massachusetts to Winnipeg in 2025

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Find the cheapest flights from Massachusetts to Winnipeg

Round-trip

One-way

Last minute

Cheap round-trip flights

7:00 pm - 2:13 pmBOS-YWG

20h 13m1 stop

6:30 am - 5:40 pmYWG-BOS

10h 10m1 stop

$310WestJet

Find Deal

Sat, Sep 27 - Sat, Oct 4

7:00 pm - 2:13 pmBOS-YWG

20h 13m1 stop

6:15 pm - 6:10 pmYWG-BOS

22h 55m2 stops

$312WestJet

Find Deal

Sat, Sep 27 - Sat, Oct 4

10:40 am - 11:41 amBOS-YWG

26h 01m2 stops

3:15 pm - 9:30 amYWG-BOS

17h 15m2 stops

$352

Find Deal

Thu, Sep 25 - Wed, Oct 1

6:00 am - 10:40 amBOS-YWG

5h 40m1 stop

7:55 am - 2:30 pmYWG-BOS

5h 35m1 stop

$365Air Canada

Find Deal

Thu, Sep 25 - Wed, Oct 1

6:00 am - 1:56 pmBOS-YWG

8h 56m2 stops

7:55 am - 2:30 pmYWG-BOS

5h 35m1 stop

$369Air Canada

Find Deal

Thu, Sep 25 - Wed, Oct 1

12:20 pm - 4:22 pmBOS-YWG

29h 02m3 stops

9:05 pm - 10:52 pmYWG-BOS

24h 47m3 stops

$377

Find Deal

Wed, Sep 10 - Mon, Oct 13

6:55 pm - 11:13 amBOS-YWG

17h 18m2 stops

12:10 pm - 10:05 pmYWG-BOS

8h 55m1 stop

$425Porter Airlines

Find Deal

Fri, Nov 14 - Tue, Nov 18

4:27 pm - 10:33 pmBOS-YWG

7h 06m1 stop

4:25 pm - 6:00 amYWG-BOS

12h 35m1 stop

$438United Airlines

Find Deal

Fri, Sep 19 - Fri, Sep 26

6:55 pm - 3:30 pmBOS-YWG

21h 35m1 stop

12:10 pm - 10:05 pmYWG-BOS

8h 55m1 stop

$443Porter Airlines

Find Deal

Fri, Nov 14 - Tue, Nov 18

5:30 am - 10:33 pmBOS-YWG

18h 03m2 stops

2:20 pm - 10:31 amYWG-BOS

19h 11m2 stops

$732United Airlines

Find Deal

Thu, Oct 9 - Mon, Oct 13

Air Canada flights from Massachusetts to Winnipeg

Our best Air Canada deals on Massachusetts to Winnipeg flight tickets

Air Canada

Sep 25

BOS6:00 amBoston Logan Intl

5h 40m

1 stop

YWG10:40 amWinnipeg

Oct 1

YWG7:55 amWinnipeg

5h 35m

1 stop

BOS2:30 pmBoston Logan Intl

$365

Find similar

Air Canada

Sep 25

BOS6:00 amBoston Logan Intl

8h 56m

2 stops

YWG1:56 pmWinnipeg

Oct 1

YWG7:55 amWinnipeg

5h 35m

1 stop

BOS2:30 pmBoston Logan Intl

$369

Find similar

Air Canada

Oct 9

BOS6:00 amBoston Logan Intl

12h 45m

1 stop

YWG5:45 pmWinnipeg

Oct 13

YWG5:00 amWinnipeg

5h 29m

1 stop

BOS11:29 amBoston Logan Intl

$407

Find similar

Delta flights from Massachusetts to Winnipeg

Our best Delta deals on Massachusetts to Winnipeg flight tickets

Delta

Sep 23

BOS5:40 amBoston Logan Intl

12h 10m

2 stops

YWG4:50 pmWinnipeg

Sep 24

YWG5:40 pmWinnipeg

5h 19m

1 stop

BOS11:59 pmBoston Logan Intl

$450

Find similar

Delta

Sep 10

BOS6:25 amBoston Logan Intl

11h 26m

2 stops

YWG4:51 pmWinnipeg

Oct 13

YWG12:20 pmWinnipeg

8h 44m

1 stop

BOS10:04 pmBoston Logan Intl

$641

Find similar

Delta

Sep 10

BOS6:25 amBoston Logan Intl

11h 26m

2 stops

YWG4:51 pmWinnipeg

Oct 13

YWG8:00 amWinnipeg

11h 23m

2 stops

BOS8:23 pmBoston Logan Intl

$745

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 9/27

7:00 pm-2:13 pm

1 stop20h 13m

Winnipeg

Sat 10/4

6:30 am-5:40 pm

1 stop10h 10m

$310

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 9/27

7:00 pm-2:13 pm

1 stop20h 13m

Winnipeg

Sat 10/4

6:15 pm-6:10 pm

2 stops22h 55m

$312

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/25

10:40 am-11:41 am

2 stops26h 01m

Winnipeg

Wed 10/1

3:15 pm-9:30 am

2 stops17h 15m

$352

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/25

6:00 am-10:40 am

1 stop5h 40m

Winnipeg

Wed 10/1

7:55 am-2:30 pm

1 stop5h 35m

$365

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/25

6:00 am-1:56 pm

2 stops8h 56m

Winnipeg

Wed 10/1

7:55 am-2:30 pm

1 stop5h 35m

$369

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/10

12:20 pm-4:22 pm

3 stops29h 02m

Winnipeg

Mon 10/13

9:05 pm-10:52 pm

3 stops24h 47m

$377

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 11/14

6:55 pm-11:13 am

2 stops17h 18m

Winnipeg

Tue 11/18

12:10 pm-10:05 pm

1 stop8h 55m

$425

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 9/19

4:27 pm-10:33 pm

1 stop7h 06m

Winnipeg

Fri 9/26

4:25 pm-6:00 am

1 stop12h 35m

$438

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 11/14

6:55 pm-3:30 pm

1 stop21h 35m

Winnipeg

Tue 11/18

12:10 pm-10:05 pm

1 stop8h 55m

$443

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/9

5:30 am-10:33 pm

2 stops18h 03m

Winnipeg

Mon 10/13

2:20 pm-10:31 am

2 stops19h 11m

$732

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, July 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 $233. If you’re not able to fly to Winnipeg in July, then May is your next best option. Flight prices from Massachusetts to Winnipeg during May average around $328.

What is the cheapest day to depart on your flight to Winnipeg?

The cheapest day to depart on your flight to Winnipeg is on a Sunday when prices can be found for as low as $354. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $789.

What is the cheapest time of day to depart on your flight to Winnipeg?

The cheapest time of day to fly to Winnipeg is at noon when flights can be purchased for as low as $405. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $552 on average. Flights to Winnipeg from Massachusetts in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

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 $444 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 $336 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

Direct flights	None

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 4 as of August 2025.
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
Air Canada	PriceFrom $134	Free Cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
United Airlines	PriceFrom $172	Free Cancellation	Rating 7.4 8,944 reviews	Search United Airlines flights
Delta	PriceFrom $274	Free Cancellation	Rating 7.9 7,977 reviews	Search Delta flights
Porter Airlines	PriceFrom $283	Free Cancellation	Rating 8.0 349 reviews	Search Porter Airlines flights

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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.