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Cheap flights from Massachusetts to Winnipeg from C$ 161

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 8/5. 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

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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
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 a.m. - 5:35 p.m.
YWG
-
BOS
7h 15m
1 stop
C$ 389Porter Airlines
Wed, 20 May - Tue, 26 May
Air Canada Logo
5:10 a.m. - 11:08 a.m.
BOS
-
YWG
6h 58m
1 stop
Air Canada Logo
8:00 a.m. - 2:47 p.m.
YWG
-
BOS
5h 47m
1 stop
C$ 393Air Canada
Wed, 20 May - Sun, 24 May
Delta Logo
5:51 a.m. - 10:54 a.m.
BOS
-
YWG
6h 03m
1 stop
Delta Logo
5:41 p.m. - 11:54 p.m.
YWG
-
BOS
5h 13m
1 stop
C$ 397Delta
Tue, 19 May - Sun, 24 May
Air Canada Logo
5:10 a.m. - 11:08 a.m.
BOS
-
YWG
6h 58m
1 stop
Air Canada Logo
3:15 p.m. - 10:39 p.m.
YWG
-
BOS
6h 24m
1 stop
C$ 400Air Canada
Thu, 28 May - Mon, 1 Jun
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 a.m. - 5:35 p.m.
YWG
-
BOS
7h 15m
1 stop
C$ 430Porter Airlines
Tue, 19 May - Tue, 26 May
United Airlines Logo
6:00 a.m. - 11:52 a.m.
ALB
-
YWG
6h 52m
1 stop
United Airlines Logo
2:00 p.m. - 12:48 a.m.
YWG
-
ALB
9h 48m
1 stop
C$ 518United Airlines
Thu, 7 May - Mon, 11 May
United Airlines Logo
6:00 a.m. - 11:52 a.m.
ALB
-
YWG
6h 52m
1 stop
United Airlines Logo
2:00 p.m. - 10:13 a.m.
YWG
-
ALB
19h 13m
2 stops
C$ 532United Airlines
Thu, 7 May - Mon, 11 May
Delta Logo
5:55 a.m. - 2:55 p.m.
ALB
-
YWG
10h 00m
2 stops
Delta Logo
11:55 a.m. - 11:18 p.m.
YWG
-
ALB
10h 23m
2 stops
C$ 539Delta
Thu, 7 May - Mon, 11 May
WestJet Logo
6:00 a.m. - 10:10 p.m.
BDL
-
YWG
17h 10m
2 stops
WestJet Logo
7:00 a.m. - 11:57 p.m.
YWG
-
BDL
15h 57m
2 stops
C$ 605WestJet
Fri, 29 May - Sun, 31 May
WestJet Logo
7:35 a.m. - 3:04 p.m.
BDL
-
YWG
8h 29m
1 stop
WestJet Logo
6:15 a.m. - 4:06 p.m.
YWG
-
BDL
8h 51m
2 stops
C$ 612WestJet
Tue, 9 Jun - Sat, 4 Jul

Porter Airlines flights from Massachusetts to Winnipeg

Our best Porter Airlines deals on Massachusetts to Winnipeg flight tickets
Porter Airlines
20 May
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
26 May
YWG9:20 a.m.Winnipeg
7h 15m
1 stop
BOS5:35 p.m.Boston Logan Intl
C$ 389
Porter Airlines
19 May
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
26 May
YWG9:20 a.m.Winnipeg
7h 15m
1 stop
BOS5:35 p.m.Boston Logan Intl
C$ 430
Porter Airlines
23 Jun
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
30 Jun
YWG9:20 a.m.Winnipeg
7h 15m
1 stop
BOS5:35 p.m.Boston Logan Intl
C$ 446

Air Canada flights from Massachusetts to Winnipeg

Our best Air Canada deals on Massachusetts to Winnipeg flight tickets
Air Canada
20 May
BOS5:10 a.m.Boston Logan Intl
6h 58m
1 stop
YWG11:08 a.m.Winnipeg
24 May
YWG8:00 a.m.Winnipeg
5h 47m
1 stop
BOS2:47 p.m.Boston Logan Intl
C$ 393
Air Canada
28 May
BOS5:10 a.m.Boston Logan Intl
6h 58m
1 stop
YWG11:08 a.m.Winnipeg
1 Jun
YWG3:15 p.m.Winnipeg
6h 24m
1 stop
BOS10:39 p.m.Boston Logan Intl
C$ 400
Air Canada
8 May
BOS5:10 a.m.Boston Logan Intl
6h 58m
1 stop
YWG11:08 a.m.Winnipeg
17 May
YWG8:00 a.m.Winnipeg
5h 47m
1 stop
BOS2:47 p.m.Boston Logan Intl
C$ 402

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 25 March 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 - YWG

BOSYWG

Boston Logan Intl

Wed 20/5

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

1 stop6h 14m

Winnipeg

Tue 26/5

9:20 a.m.-5:35 p.m.

1 stop7h 15m

C$ 389

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 20/5

5:10 a.m.-11:08 a.m.

1 stop6h 58m

Winnipeg

Sun 24/5

8:00 a.m.-2:47 p.m.

1 stop5h 47m

C$ 393
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 19/5

5:51 a.m.-10:54 a.m.

1 stop6h 03m

Winnipeg

Sun 24/5

5:41 p.m.-11:54 p.m.

1 stop5h 13m

C$ 397

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 28/5

5:10 a.m.-11:08 a.m.

1 stop6h 58m

Winnipeg

Mon 1/6

3:15 p.m.-10:39 p.m.

1 stop6h 24m

C$ 400

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 19/5

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

1 stop6h 14m

Winnipeg

Tue 26/5

9:20 a.m.-5:35 p.m.

1 stop7h 15m

C$ 430

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Thu 7/5

6:00 a.m.-11:52 a.m.

1 stop6h 52m

Winnipeg

Mon 11/5

2:00 p.m.-12:48 a.m.

1 stop9h 48m

C$ 518

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Thu 7/5

6:00 a.m.-11:52 a.m.

1 stop6h 52m

Winnipeg

Mon 11/5

2:00 p.m.-10:13 a.m.

2 stops19h 13m

C$ 532

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Thu 7/5

5:55 a.m.-2:55 p.m.

2 stops10h 00m

Winnipeg

Mon 11/5

11:55 a.m.-11:18 p.m.

2 stops10h 23m

C$ 539

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Fri 29/5

6:00 a.m.-10:10 p.m.

2 stops17h 10m

Winnipeg

Sun 31/5

7:00 a.m.-11:57 p.m.

2 stops15h 57m

C$ 605

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Tue 9/6

7:35 a.m.-3:04 p.m.

1 stop8h 29m

Winnipeg

Sat 4/7

6:15 a.m.-4:06 p.m.

2 stops8h 51m

C$ 612

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest 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$ 352, 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 August is also very affordable. Most momondo users find prices during this month for around C$ 578.

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$ 702 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$ 513 on momondo.

Can stopping save me money on Massachusetts to Winnipeg flights?

You could potentially save up to 11% 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 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 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
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.

An easier way to manage your Winnipeg trip

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