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 61% 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.

How long does it take to fly to Winnipeg?

If you’re flying from a popular airport in Massachusetts, such as Boston or Provincetown, and flying into Winnipeg, then you can expect flight times to average 5h 21m and 21h 45m, respectively.

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

Delta and Porter 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 October 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 2026/27

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.

10:50 am - 4:27 pmBOS Boston Logan Intl-YWG Winnipeg

6h 37m1 stop Toronto Pearson Intl

3:40 pm - 10:40 pmYWG Winnipeg-BOS Boston Logan Intl

6h 00m1 stop Toronto Pearson Intl

$288Air Canada

Sun, Oct 11 - Sat, Oct 17

7:00 am - 5:58 pmBOS Boston Logan Intl-YWG Winnipeg

11h 58m2 stops Toronto Island Ottawa

3:40 pm - 10:40 pmYWG Winnipeg-BOS Boston Logan Intl

6h 00m1 stop Toronto Pearson Intl

$288Multiple Airlines

Sun, Oct 11 - Sat, Oct 17

7:00 am - 5:58 pmBOS Boston Logan Intl-YWG Winnipeg

11h 58m2 stops Toronto Island Ottawa

5:00 am - 2:41 pmYWG Winnipeg-BOS Boston Logan Intl

8h 41m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$291Multiple Airlines

Sun, Oct 11 - Sat, Oct 17

10:05 am - 3:20 pmBOS Boston Logan Intl-YWG Winnipeg

6h 15m1 stop Toronto Pearson Intl

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

8h 15m1 stop Toronto Pearson Intl

$292Porter Airlines

Fri, Oct 16 - Mon, Oct 19

10:05 am - 3:20 pmBOS Boston Logan Intl-YWG Winnipeg

6h 15m1 stop Toronto Pearson Intl

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

8h 15m1 stop Toronto Pearson Intl

$312Porter Airlines

Fri, Oct 16 - Mon, Oct 19

3:00 pm - 12:34 amBOS Boston Logan Intl-YWG Winnipeg

9h 34m1 stop Minneapolis St Paul

5:38 pm - 10:53 pmYWG Winnipeg-BOS Boston Logan Intl

5h 15m1 stop Minneapolis St Paul

$324Delta

Thu, Feb 4 - Sun, Feb 7

7:27 am - 4:50 pmBOS Boston Logan Intl-YWG Winnipeg

10h 23m1 stop Minneapolis St Paul

5:40 pm - 11:20 pmYWG Winnipeg-BOS Boston Logan Intl

5h 40m1 stop Minneapolis St Paul

$324Delta

Sat, Oct 31 - Sat, Nov 7

7:01 am - 12:37 pmBOS Boston Logan Intl-YWG Winnipeg

6h 36m1 stop Chicago O'Hare Intl

8:45 am - 11:59 pmYWG Winnipeg-BOS Boston Logan Intl

14h 14m1 stop Denver Intl

$331United Airlines

Fri, Oct 16 - Mon, Oct 19

7:01 am - 12:37 pmBOS Boston Logan Intl-YWG Winnipeg

6h 36m1 stop Chicago O'Hare Intl

7:00 am - 12:54 amYWG Winnipeg-BOS Boston Logan Intl

16h 54m1 stop Chicago O'Hare Intl

$331United Airlines

Fri, Oct 16 - Mon, Oct 19

5:50 am - 4:27 pmBOS Boston Logan Intl-YWG Winnipeg

11h 37m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

5:00 am - 11:50 amYWG Winnipeg-BOS Boston Logan Intl

5h 50m1 stop Toronto Pearson Intl

$341Air Canada

Fri, Oct 16 - Mon, Oct 19

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Air Canada flights from Massachusetts to Winnipeg

Our best Air Canada deals on Massachusetts to Winnipeg flight tickets

Air Canada

Oct 11

BOS10:50 amBoston Logan Intl

6h 37m

1 stop

YWG4:27 pmWinnipeg

Oct 17

YWG3:40 pmWinnipeg

6h 00m

1 stop

BOS10:40 pmBoston Logan Intl

$288

Air Canada

Oct 16

BOS5:50 amBoston Logan Intl

11h 37m

2 stops

YWG4:27 pmWinnipeg

Oct 19

YWG5:00 amWinnipeg

5h 50m

1 stop

BOS11:50 amBoston Logan Intl

$341

Air Canada

Oct 22

BOS5:50 amBoston Logan Intl

13h 22m

2 stops

YWG6:12 pmWinnipeg

Oct 24

YWG5:00 amWinnipeg

5h 50m

1 stop

BOS11:50 amBoston Logan Intl

$365

Porter Airlines flights from Massachusetts to Winnipeg

Our best Porter Airlines deals on Massachusetts to Winnipeg flight tickets

Porter Airlines

Oct 16

BOS10:05 amBoston Logan Intl

6h 15m

1 stop

YWG3:20 pmWinnipeg

Oct 19

YWG9:20 amWinnipeg

8h 15m

1 stop

BOS6:35 pmBoston Logan Intl

$292

Porter Airlines

Oct 16

BOS10:05 amBoston Logan Intl

6h 15m

1 stop

YWG3:20 pmWinnipeg

Oct 19

YWG9:20 amWinnipeg

8h 15m

1 stop

BOS6:35 pmBoston Logan Intl

$312

Porter Airlines

Oct 16

BOS7:00 amBoston Logan Intl

11h 58m

2 stops

YWG5:58 pmWinnipeg

Oct 19

YWG9:20 amWinnipeg

8h 15m

1 stop

BOS6:35 pmBoston Logan Intl

$315

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sun 10/11

10:50 am-4:27 pm

1 stop6h 37m

Winnipeg

Sat 10/17

3:40 pm-10:40 pm

1 stop6h 00m

$288

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sun 10/11

7:00 am-5:58 pm

2 stops11h 58m

Winnipeg

Sat 10/17

3:40 pm-10:40 pm

1 stop6h 00m

$288

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sun 10/11

7:00 am-5:58 pm

2 stops11h 58m

Winnipeg

Sat 10/17

5:00 am-2:41 pm

2 stops8h 41m

$291

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 10/16

10:05 am-3:20 pm

1 stop6h 15m

Winnipeg

Mon 10/19

9:20 am-6:35 pm

1 stop8h 15m

$292

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 10/16

10:05 am-3:20 pm

1 stop6h 15m

Winnipeg

Mon 10/19

9:20 am-6:35 pm

1 stop8h 15m

$312

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 2/4

3:00 pm-12:34 am

1 stop9h 34m

Winnipeg

Sun 2/7

5:38 pm-10:53 pm

1 stop5h 15m

$324

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 10/31

7:27 am-4:50 pm

1 stop10h 23m

Winnipeg

Sat 11/7

5:40 pm-11:20 pm

1 stop5h 40m

$324

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 10/16

7:01 am-12:37 pm

1 stop6h 36m

Winnipeg

Mon 10/19

8:45 am-11:59 pm

1 stop14h 14m

$331

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 10/16

7:01 am-12:37 pm

1 stop6h 36m

Winnipeg

Mon 10/19

7:00 am-12:54 am

1 stop16h 54m

$331

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 10/16

5:50 am-4:27 pm

2 stops11h 37m

Winnipeg

Mon 10/19

5:00 am-11:50 am

1 stop5h 50m

$341

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

Other information

What is the cheapest month to fly to Winnipeg?

In general, September 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 $364. If you’re not able to fly to Winnipeg in September, then August is your next best option. Flight prices from Massachusetts to Winnipeg during August average around $437.

Cheap Massachusetts to Winnipeg flight deals and tips

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

Best Price Found	$135
Fastest flight time	5h 21m
Direct flights	None

The best one-way flight to Winnipeg from Massachusetts in the past 72 hours is $135. The best round-trip flight deal from Massachusetts to Winnipeg found on momondo in the last 72 hours is $288.

The fastest flight from Massachusetts to Winnipeg takes 5h 21m

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 October 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 10,273 reviews	Search United Airlines flights
Air Canada	PriceFrom $204	Free Cancellation	Rating 7.1 11,711 reviews	Search Air Canada flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.8 8,620 reviews	Search Delta flights
Porter Airlines	PriceFrom $352	Free Cancellation	Rating 8.0 468 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.