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Cheap flights from Massachusetts to Winnipeg from C$ 176

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Winnipeg departing on 29/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Massachusetts to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 14m1 stop Toronto Pearson Intl
Porter Airlines Logo
12:15 p.m. - 7:15 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 00m1 stop Toronto Pearson Intl
C$ 385Porter Airlines
Sat, 29 Aug - Sat, 5 Sep
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 14m1 stop Toronto Pearson Intl
Porter Airlines Logo
12:15 p.m. - 7:15 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 00m1 stop Toronto Pearson Intl
C$ 411Porter Airlines
Sat, 29 Aug - Sat, 5 Sep
Air Canada Logo
12:30 p.m. - 6:12 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 42m1 stop Toronto Pearson Intl
Air Canada Logo
2:05 p.m. - 10:40 p.m.YWG  Winnipeg-BOS Boston Logan Intl
7h 35m1 stop Toronto Pearson Intl
C$ 417Air Canada
Thu, 10 Sep - Mon, 14 Sep
Multiple Airlines Logo
10:05 a.m. - 3:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 14m1 stop Toronto Pearson Intl
Multiple Airlines Logo
7:00 a.m. - 5:40 p.m.YWG  Winnipeg-BOS Boston Logan Intl
9h 40m1 stop Calgary
C$ 422Multiple Airlines
Fri, 9 Oct - Sun, 11 Oct
Air Canada Logo
5:50 a.m. - 4:27 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 37m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
3:20 p.m. - 10:40 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 20m1 stop Toronto Pearson Intl
C$ 429Air Canada
Thu, 10 Sep - Mon, 14 Sep
Air Canada Logo
10:40 a.m. - 3:09 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 29m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:10 a.m. - 2:41 p.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 31m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 433Air Canada
Thu, 1 Oct - Mon, 5 Oct
Air Canada Logo
5:50 a.m. - 4:27 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 37m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
5:00 a.m. - 2:41 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 41m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
C$ 442Air Canada
Thu, 10 Sep - Mon, 14 Sep
Delta Logo
7:10 a.m. - 4:52 p.m.BOS  Boston Logan Intl-YWG Winnipeg
10h 42m1 stop Minneapolis St Paul
Delta Logo
3:58 p.m. - 11:59 p.m.YWG  Winnipeg-BOS Boston Logan Intl
7h 01m1 stop Minneapolis St Paul
C$ 443Delta
Thu, 3 Sep - Wed, 9 Sep
Air Canada Logo
5:50 a.m. - 2:22 p.m.BOS  Boston Logan Intl-YWG Winnipeg
9h 32m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
1:25 p.m. - 9:26 p.m.YWG  Winnipeg-BOS Boston Logan Intl
7h 01m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
C$ 460Air Canada
Thu, 1 Oct - Mon, 5 Oct
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 14m1 stop Toronto Pearson Intl
Porter Airlines Logo
9:20 a.m. - 6:35 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 15m1 stop Toronto Pearson Intl
C$ 481Porter Airlines
Thu, 1 Oct - Mon, 5 Oct

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WestJet flights from Massachusetts to Winnipeg

Our best WestJet deals on Massachusetts to Winnipeg flight tickets
WestJet
3 Oct
BOS6:30 p.m.Boston Logan Intl
18h 45m
1 stop
YWG12:15 p.m.Winnipeg
13 Oct
YWG6:00 a.m.Winnipeg
10h 40m
1 stop
BOS5:40 p.m.Boston Logan Intl
C$ 483
WestJet
1 Sep
BOS7:25 a.m.Boston Logan Intl
13h 35m
2 stops
YWG8:00 p.m.Winnipeg
10 Sep
YWG6:00 a.m.Winnipeg
10h 40m
1 stop
BOS5:40 p.m.Boston Logan Intl
C$ 507
WestJet
1 Sep
BOS7:25 a.m.Boston Logan Intl
26h 55m
2 stops
YWG9:20 a.m.Winnipeg
5 Sep
YWG12:00 p.m.Winnipeg
9h 20m
1 stop
BOS10:20 p.m.Boston Logan Intl
C$ 532

Porter Airlines flights from Massachusetts to Winnipeg

Our best Porter Airlines deals on Massachusetts to Winnipeg flight tickets
Porter Airlines
29 Aug
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
5 Sep
YWG12:15 p.m.Winnipeg
6h 00m
1 stop
BOS7:15 p.m.Boston Logan Intl
C$ 385
Porter Airlines
29 Aug
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
5 Sep
YWG12:15 p.m.Winnipeg
6h 00m
1 stop
BOS7:15 p.m.Boston Logan Intl
C$ 411
Porter Airlines
1 Oct
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
5 Oct
YWG9:20 a.m.Winnipeg
8h 15m
1 stop
BOS6:35 p.m.Boston Logan Intl
C$ 481

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 14 August 2026.
Use the filters below to find and compare flights from Massachusetts to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 29/8

10:05 a.m.-3:19 p.m.

1 stop6h 14m

Winnipeg

Sat 5/9

12:15 p.m.-7:15 p.m.

1 stop6h 00m

C$ 385

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 29/8

10:05 a.m.-3:19 p.m.

1 stop6h 14m

Winnipeg

Sat 5/9

12:15 p.m.-7:15 p.m.

1 stop6h 00m

C$ 411

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 10/9

12:30 p.m.-6:12 p.m.

1 stop6h 42m

Winnipeg

Mon 14/9

2:05 p.m.-10:40 p.m.

1 stop7h 35m

C$ 417

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 9/10

10:05 a.m.-3:19 p.m.

1 stop6h 14m

Winnipeg

Sun 11/10

7:00 a.m.-5:40 p.m.

1 stop9h 40m

C$ 422

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 10/9

5:50 a.m.-4:27 p.m.

2 stops11h 37m

Winnipeg

Mon 14/9

3:20 p.m.-10:40 p.m.

1 stop6h 20m

C$ 429
Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 1/10

10:40 a.m.-3:09 p.m.

1 stop5h 29m

Winnipeg

Mon 5/10

8:10 a.m.-2:41 p.m.

1 stop5h 31m

C$ 433

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 10/9

5:50 a.m.-4:27 p.m.

2 stops11h 37m

Winnipeg

Mon 14/9

5:00 a.m.-2:41 p.m.

2 stops8h 41m

C$ 442

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 3/9

7:10 a.m.-4:52 p.m.

1 stop10h 42m

Winnipeg

Wed 9/9

3:58 p.m.-11:59 p.m.

1 stop7h 01m

C$ 443

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 1/10

5:50 a.m.-2:22 p.m.

2 stops9h 32m

Winnipeg

Mon 5/10

1:25 p.m.-9:26 p.m.

2 stops7h 01m

C$ 460

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 1/10

10:05 a.m.-3:19 p.m.

1 stop6h 14m

Winnipeg

Mon 5/10

9:20 a.m.-6:35 p.m.

1 stop8h 15m

C$ 481

Flights are sorted by cheapest round-trip flights first.

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See travel insights to Winnipeg from

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

What is the cheapest month to fly to Winnipeg?

The cheapest month to fly to Winnipeg from Massachusetts is in May. Flight prices, which tend to average around C$ 718, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of May, then departing from Massachusetts during the month October is also very affordable. Most momondo users find prices during this month for around C$ 721.

Can stopping save me money on Massachusetts to Winnipeg flights?

You could potentially save up to 35% on your flight if you consider stops on a Massachusetts to Winnipeg flight.

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 35m

Direct flights

None
The fastest flight from Massachusetts to Winnipeg takes 5h 35m
There are no direct flights from Massachusetts to Winnipeg. There are no popular flight routes from Massachusetts to Winnipeg.
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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 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.

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie
Morden
Selkirk

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.

An easier way to manage your Winnipeg trip

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