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Cheap flights from Massachusetts to Winnipeg from C$ 205

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 11/6. 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$ 443Porter Airlines
Wed, 8 Jul - Wed, 15 Jul
Porter Airlines Logo
7:10 a.m. - 5:58 p.m.
BOS
-
YWG
11h 48m
2 stops
Porter Airlines Logo
9:20 a.m. - 5:35 p.m.
YWG
-
BOS
7h 15m
1 stop
C$ 446Porter Airlines
Wed, 8 Jul - Wed, 15 Jul
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$ 451Porter Airlines
Thu, 17 Sep - Tue, 29 Sep
Porter Airlines Logo
7:10 a.m. - 5:58 p.m.
BOS
-
YWG
11h 48m
2 stops
Porter Airlines Logo
9:20 a.m. - 5:35 p.m.
YWG
-
BOS
7h 15m
1 stop
C$ 453Porter Airlines
Thu, 17 Sep - Tue, 29 Sep
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$ 458Porter Airlines
Wed, 8 Jul - Wed, 15 Jul
WestJet Logo
6:00 a.m. - 12:55 a.m.
ALB
-
YWG
19h 55m
2 stops
WestJet Logo
10:45 a.m. - 11:06 p.m.
YWG
-
ALB
11h 21m
2 stops
C$ 682WestJet
Tue, 8 Sep - Sun, 20 Sep
WestJet Logo
6:06 a.m. - 12:55 a.m.
ALB
-
YWG
19h 49m
2 stops
WestJet Logo
6:15 a.m. - 11:35 a.m.
YWG
-
ALB
28h 20m
2 stops
C$ 699WestJet
Mon, 8 Jun - Wed, 10 Jun
Delta Logo
9:36 a.m. - 11:29 p.m.
ALB
-
YWG
14h 53m
2 stops
Delta Logo
6:40 a.m. - 9:04 p.m.
YWG
-
ALB
13h 24m
2 stops
C$ 711Delta
Sat, 20 Jun - Sat, 27 Jun
United Airlines Logo
1:00 p.m. - 10:33 p.m.
ALB
-
YWG
10h 33m
1 stop
United Airlines Logo
7:40 p.m. - 5:34 p.m.
YWG
-
ALB
20h 54m
2 stops
C$ 789United Airlines
Wed, 19 Aug - Sun, 23 Aug
United Airlines Logo
4:50 p.m. - 10:33 p.m.
BDL
-
YWG
6h 43m
1 stop
United Airlines Logo
7:00 a.m. - 2:29 p.m.
YWG
-
BDL
6h 29m
1 stop
C$ 886United Airlines
Wed, 2 Sep - Mon, 7 Sep

Air Canada flights from Massachusetts to Winnipeg

Our best Air Canada deals on Massachusetts to Winnipeg flight tickets
Air Canada
22 Oct
BOS10:40 a.m.Boston Logan Intl
5h 29m
1 stop
YWG3:09 p.m.Winnipeg
24 Oct
YWG8:10 a.m.Winnipeg
5h 31m
1 stop
BOS2:41 p.m.Boston Logan Intl
C$ 487
Air Canada
22 Oct
BOS10:40 a.m.Boston Logan Intl
5h 29m
1 stop
YWG3:09 p.m.Winnipeg
24 Oct
YWG8:10 a.m.Winnipeg
5h 31m
1 stop
BOS2:41 p.m.Boston Logan Intl
C$ 488
Air Canada
9 Sep
BOS10:50 a.m.Boston Logan Intl
6h 27m
1 stop
YWG4:17 p.m.Winnipeg
12 Sep
YWG8:10 a.m.Winnipeg
5h 31m
1 stop
BOS2:41 p.m.Boston Logan Intl
C$ 495

United Airlines flights from Massachusetts to Winnipeg

Our best United Airlines deals on Massachusetts to Winnipeg flight tickets
United Airlines
8 Jul
BOS3:08 p.m.Boston Logan Intl
8h 30m
1 stop
YWG10:38 p.m.Winnipeg
15 Jul
YWG8:45 a.m.Winnipeg
22h 32m
2 stops
BOS8:17 a.m.Boston Logan Intl
C$ 570
United Airlines
19 Aug
ALB1:00 p.m.Albany Intl
10h 33m
1 stop
YWG10:33 p.m.Winnipeg
23 Aug
YWG7:40 p.m.Winnipeg
20h 54m
2 stops
ALB5:34 p.m.Albany Intl
C$ 789
United Airlines
19 Aug
ALB1:00 p.m.Albany Intl
10h 33m
1 stop
YWG10:33 p.m.Winnipeg
23 Aug
YWG7:00 a.m.Winnipeg
9h 34m
1 stop
ALB5:34 p.m.Albany Intl
C$ 830

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 10 May 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 8/7

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

1 stop6h 14m

Winnipeg

Wed 15/7

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

1 stop7h 15m

C$ 443

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 8/7

7:10 a.m.-5:58 p.m.

2 stops11h 48m

Winnipeg

Wed 15/7

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

1 stop7h 15m

C$ 446

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 17/9

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

1 stop6h 14m

Winnipeg

Tue 29/9

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

1 stop7h 15m

C$ 451

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 17/9

7:10 a.m.-5:58 p.m.

2 stops11h 48m

Winnipeg

Tue 29/9

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

1 stop7h 15m

C$ 453

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 8/7

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

1 stop6h 14m

Winnipeg

Wed 15/7

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

1 stop7h 15m

C$ 458

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Tue 8/9

6:00 a.m.-12:55 a.m.

2 stops19h 55m

Winnipeg

Sun 20/9

10:45 a.m.-11:06 p.m.

2 stops11h 21m

C$ 682

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Mon 8/6

6:06 a.m.-12:55 a.m.

2 stops19h 49m

Winnipeg

Wed 10/6

6:15 a.m.-11:35 a.m.

2 stops28h 20m

C$ 699

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Sat 20/6

9:36 a.m.-11:29 p.m.

2 stops14h 53m

Winnipeg

Sat 27/6

6:40 a.m.-9:04 p.m.

2 stops13h 24m

C$ 711

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Wed 19/8

1:00 p.m.-10:33 p.m.

1 stop10h 33m

Winnipeg

Sun 23/8

7:40 p.m.-5:34 p.m.

2 stops20h 54m

C$ 789
Quickest round-trip

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Wed 2/9

4:50 p.m.-10:33 p.m.

1 stop6h 43m

Winnipeg

Mon 7/9

7:00 a.m.-2:29 p.m.

1 stop6h 29m

C$ 886

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 June. Flight prices, which tend to average around C$ 150, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of June, then departing from Massachusetts during the month May is also very affordable. Most momondo users find prices during this month for around C$ 152.

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

6h 12m

Direct flights

None
The fastest flight from Massachusetts to Winnipeg takes 6h 12m
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
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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