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

Air Canada, United Airlines, and American Airlines are the most popular carriers operating from Massachusetts to Winnipeg

How long does it take to fly to Winnipeg?

On average, it takes 9h 22m to fly from Massachusetts to Winnipeg if you fly out of Boston (the most popular airport in Massachusetts) and into Winnipeg (the most popular airport in Winnipeg). If you’re flying out of Provincetown and into Winnipeg, then the flight time is around 21h 45m.

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

Prices for flights from Massachusetts to Winnipeg Airport were last updated today.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Winnipeg Airport.

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

The travel and health documents required for your trip to Winnipeg Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Winnipeg Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

C$ 211 Cheap Flights from Massachusetts to Winnipeg in 2025/26

1 adult

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Find the cheapest flights from Massachusetts to Winnipeg

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 a.m. - 3:07 p.m.BOS-YWG

10h 07m1 stop

7:30 a.m. - 12:58 a.m.YWG-BOS

16h 28m1 stop

C$ 365Multiple Airlines

Find Deal

Wed, 14 Jan - Sun, 18 Jan

6:15 a.m. - 7:35 p.m.BOS-YWG

14h 20m2 stops

7:30 a.m. - 12:58 a.m.YWG-BOS

16h 28m1 stop

C$ 519Multiple Airlines

Find Deal

Wed, 14 Jan - Sun, 18 Jan

5:30 a.m. - 10:16 a.m.BOS-YWG

5h 46m1 stop

5:30 a.m. - 12:12 p.m.YWG-BOS

5h 42m1 stop

C$ 545Air Canada

Find Deal

Fri, 16 Jan - Mon, 19 Jan

6:00 a.m. - 11:43 a.m.BDL-YWG

6h 43m1 stop

5:38 p.m. - 11:38 p.m.YWG-BDL

5h 00m1 stop

C$ 608Delta

Find Deal

Tue, 10 Mar - Wed, 11 Mar

2:48 p.m. - 11:39 a.m.BDL-YWG

21h 51m2 stops

2:15 p.m. - 9:35 p.m.YWG-BDL

6h 20m1 stop

C$ 621United Airlines

Find Deal

Tue, 10 Mar - Wed, 11 Mar

7:50 p.m. - 11:57 a.m.BDL-YWG

17h 07m2 stops

8:40 a.m. - 9:38 a.m.YWG-BDL

23h 58m2 stops

C$ 628United Airlines

Find Deal

Wed, 3 Dec - Wed, 10 Dec

6:00 a.m. - 11:43 a.m.BDL-YWG

6h 43m1 stop

12:40 p.m. - 11:38 p.m.YWG-BDL

9h 58m1 stop

C$ 657Delta

Find Deal

Tue, 10 Mar - Wed, 11 Mar

5:30 a.m. - 10:16 a.m.BOS-YWG

5h 46m1 stop

5:30 a.m. - 12:12 p.m.YWG-BOS

5h 42m1 stop

C$ 735Air Canada

Find Deal

Tue, 23 Dec - Wed, 31 Dec

9:00 a.m. - 11:35 p.m.BDL-YWG

15h 35m3 stops

12:10 p.m. - 10:20 p.m.YWG-BDL

9h 10m2 stops

C$ 1,045American Airlines

Find Deal

Wed, 26 Nov - Wed, 10 Dec

7:42 p.m. - 11:35 p.m.BDL-YWG

28h 53m3 stops

12:10 p.m. - 4:37 p.m.YWG-BDL

27h 27m3 stops

C$ 1,266American Airlines

Find Deal

Wed, 3 Dec - Wed, 10 Dec

United Airlines flights from Massachusetts to Winnipeg

Our best United Airlines deals on Massachusetts to Winnipeg flight tickets

United Airlines

10 Mar

BDL2:48 p.m.Hartford Bradley Intl

21h 51m

2 stops

YWG11:39 a.m.Winnipeg

11 Mar

YWG2:15 p.m.Winnipeg

6h 20m

1 stop

BDL9:35 p.m.Hartford Bradley Intl

C$ 621

Find similar

United Airlines

3 Dec

BDL7:50 p.m.Hartford Bradley Intl

17h 07m

2 stops

YWG11:57 a.m.Winnipeg

10 Dec

YWG8:40 a.m.Winnipeg

23h 58m

2 stops

BDL9:38 a.m.Hartford Bradley Intl

C$ 628

Find similar

United Airlines

10 Mar

BDL2:48 p.m.Hartford Bradley Intl

21h 51m

2 stops

YWG11:39 a.m.Winnipeg

11 Mar

YWG2:15 p.m.Winnipeg

8h 35m

2 stops

BDL11:50 p.m.Hartford Bradley Intl

C$ 629

Find similar

Delta flights from Massachusetts to Winnipeg

Our best Delta deals on Massachusetts to Winnipeg flight tickets

Delta

10 Mar

BDL6:00 a.m.Hartford Bradley Intl

6h 43m

1 stop

YWG11:43 a.m.Winnipeg

11 Mar

YWG5:38 p.m.Winnipeg

5h 00m

1 stop

BDL11:38 p.m.Hartford Bradley Intl

C$ 608

Find similar

Delta

10 Mar

BDL6:00 a.m.Hartford Bradley Intl

6h 43m

1 stop

YWG11:43 a.m.Winnipeg

11 Mar

YWG12:40 p.m.Winnipeg

9h 58m

1 stop

BDL11:38 p.m.Hartford Bradley Intl

C$ 657

Find similar

Delta

2 Dec

BDL3:10 p.m.Hartford Bradley Intl

9h 34m

1 stop

YWG11:44 p.m.Winnipeg

10 Dec

YWG5:45 p.m.Winnipeg

5h 11m

1 stop

BDL11:56 p.m.Hartford Bradley Intl

C$ 718

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 14/1

6:00 a.m.-3:07 p.m.

1 stop10h 07m

Winnipeg

Sun 18/1

7:30 a.m.-12:58 a.m.

1 stop16h 28m

C$ 365

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 14/1

6:15 a.m.-7:35 p.m.

2 stops14h 20m

Winnipeg

Sun 18/1

7:30 a.m.-12:58 a.m.

1 stop16h 28m

C$ 519

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 16/1

5:30 a.m.-10:16 a.m.

1 stop5h 46m

Winnipeg

Mon 19/1

5:30 a.m.-12:12 p.m.

1 stop5h 42m

C$ 545

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Tue 10/3

6:00 a.m.-11:43 a.m.

1 stop6h 43m

Winnipeg

Wed 11/3

5:38 p.m.-11:38 p.m.

1 stop5h 00m

C$ 608

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Tue 10/3

2:48 p.m.-11:39 a.m.

2 stops21h 51m

Winnipeg

Wed 11/3

2:15 p.m.-9:35 p.m.

1 stop6h 20m

C$ 621

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Wed 3/12

7:50 p.m.-11:57 a.m.

2 stops17h 07m

Winnipeg

Wed 10/12

8:40 a.m.-9:38 a.m.

2 stops23h 58m

C$ 628

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Tue 10/3

6:00 a.m.-11:43 a.m.

1 stop6h 43m

Winnipeg

Wed 11/3

12:40 p.m.-11:38 p.m.

1 stop9h 58m

C$ 657

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 23/12

5:30 a.m.-10:16 a.m.

1 stop5h 46m

Winnipeg

Wed 31/12

5:30 a.m.-12:12 p.m.

1 stop5h 42m

C$ 735

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Wed 26/11

9:00 a.m.-11:35 p.m.

3 stops15h 35m

Winnipeg

Wed 10/12

12:10 p.m.-10:20 p.m.

2 stops9h 10m

C$ 1,045

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Wed 3/12

7:42 p.m.-11:35 p.m.

3 stops28h 53m

Winnipeg

Wed 10/12

12:10 p.m.-4:37 p.m.

3 stops27h 27m

C$ 1,266

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?

The cheapest month to fly to Winnipeg from Massachusetts is in July. Flight prices, which tend to average around C$ 328, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of July, then departing from Massachusetts during the month January is also very affordable. Most momondo users find prices during this month for around C$ 480.

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

Our data shows that Wednesday is the least expensive day to fly to Winnipeg. Tickets to fly out on this day can be as low as C$ 632. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Thursday is C$ 851.

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 C$ 611 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 C$ 410 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.

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When did momondo last update prices for flights from Massachusetts to Winnipeg Airport?
Prices for flights from Massachusetts to Winnipeg Airport were last updated today.
How old do you have to be to fly from Massachusetts to Winnipeg Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The travel and health documents required for your trip to Winnipeg Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Winnipeg Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Morden

Selkirk

Portage la Prairie

Why use momondo?

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

It is quick and easy to find Massachusetts to Winnipeg flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Winnipeg that suits you.

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

Yes. momondo enables you to select and highlight flights to Winnipeg from Massachusetts with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Winnipeg from Massachusetts.

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

If you are simply researching potential flights to Winnipeg, momondo offers a useful price alert feature which will track prices for flights to Winnipeg from Massachusetts and alert you when they change.