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Cheap flights from Massachusetts to Winnipeg from C$ 227

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 18/7. 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.
Multiple Airlines Logo
10:05 a.m. - 5:15 p.m.
BOS
-
YWG
8h 10m
1 stop
Multiple Airlines Logo
11:15 a.m. - 9:05 a.m.
YWG
-
BOS
20h 50m
2 stops
C$ 477Multiple Airlines
Wed, 16 Sep - Wed, 23 Sep
Multiple Airlines Logo
7:30 p.m. - 12:55 a.m.
BOS
-
YWG
6h 25m
1 stop
Multiple Airlines Logo
6:05 p.m. - 9:05 a.m.
YWG
-
BOS
14h 00m
1 stop
C$ 485Multiple Airlines
Wed, 16 Sep - Wed, 23 Sep
Porter Airlines Logo
8:00 a.m. - 6:10 p.m.
BOS
-
YWG
11h 10m
2 stops
Porter Airlines Logo
7:05 p.m. - 12:32 p.m.
YWG
-
BOS
16h 27m
1 stop
C$ 490Porter Airlines
Fri, 30 Oct - Mon, 2 Nov
Multiple Airlines Logo
10:05 a.m. - 5:15 p.m.
BOS
-
YWG
8h 10m
1 stop
Multiple Airlines Logo
11:15 a.m. - 6:35 p.m.
YWG
-
BOS
30h 20m
2 stops
C$ 495Multiple Airlines
Wed, 23 Sep - Wed, 30 Sep
Multiple Airlines Logo
7:30 p.m. - 12:55 a.m.
BOS
-
YWG
6h 25m
1 stop
Multiple Airlines Logo
11:15 a.m. - 9:05 a.m.
YWG
-
BOS
20h 50m
2 stops
C$ 501Multiple Airlines
Fri, 28 Aug - Mon, 31 Aug
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
12:15 p.m. - 6:35 p.m.
YWG
-
BOS
5h 20m
1 stop
C$ 504Porter Airlines
Mon, 13 Jul - Mon, 27 Jul
WestJet Logo
6:50 a.m. - 3:08 p.m.
BDL
-
YWG
9h 18m
1 stop
WestJet Logo
10:45 a.m. - 11:51 p.m.
YWG
-
BDL
12h 06m
2 stops
C$ 998WestJet
Wed, 2 Sep - Mon, 7 Sep
WestJet Logo
5:30 a.m. - 12:55 a.m.
BDL
-
YWG
20h 25m
2 stops
WestJet Logo
7:00 a.m. - 11:25 p.m.
YWG
-
BDL
15h 25m
2 stops
C$ 999WestJet
Tue, 11 Aug - Fri, 14 Aug
Delta Logo
6:50 a.m. - 11:54 a.m.
BDL
-
YWG
6h 04m
1 stop
Delta Logo
5:42 p.m. - 11:25 p.m.
YWG
-
BDL
4h 43m
1 stop
C$ 1,009Delta
Tue, 11 Aug - Fri, 14 Aug
United Airlines Logo
6:00 a.m. - 10:33 p.m.
BDL
-
YWG
17h 33m
2 stops
United Airlines Logo
7:00 a.m. - 2:29 p.m.
YWG
-
BDL
6h 29m
1 stop
C$ 1,023United Airlines
Sun, 20 Sep - Wed, 23 Sep

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Porter Airlines flights from Massachusetts to Winnipeg

Our best Porter Airlines deals on Massachusetts to Winnipeg flight tickets
Porter Airlines
30 Oct
BOS8:00 a.m.Boston Logan Intl
11h 10m
2 stops
YWG6:10 p.m.Winnipeg
2 Nov
YWG7:05 p.m.Winnipeg
16h 27m
1 stop
BOS12:32 p.m.Boston Logan Intl
C$ 490
Porter Airlines
13 Jul
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
27 Jul
YWG12:15 p.m.Winnipeg
5h 20m
1 stop
BOS6:35 p.m.Boston Logan Intl
C$ 504
Porter Airlines
13 Jul
BOS7:10 a.m.Boston Logan Intl
11h 48m
2 stops
YWG5:58 p.m.Winnipeg
27 Jul
YWG12:15 p.m.Winnipeg
5h 20m
1 stop
BOS6:35 p.m.Boston Logan Intl
C$ 508

United Airlines flights from Massachusetts to Winnipeg

Our best United Airlines deals on Massachusetts to Winnipeg flight tickets
United Airlines
18 Aug
BOS8:31 p.m.Boston Logan Intl
16h 21m
1 stop
YWG11:52 a.m.Winnipeg
21 Aug
YWG2:00 p.m.Winnipeg
10h 11m
1 stop
BOS1:11 a.m.Boston Logan Intl
C$ 603
United Airlines
8 Jul
BOS12:35 p.m.Boston Logan Intl
11h 03m
2 stops
YWG10:38 p.m.Winnipeg
11 Jul
YWG7:00 a.m.Winnipeg
14h 12m
2 stops
BOS10:12 p.m.Boston Logan Intl
C$ 776
United Airlines
11 Aug
BDL4:50 p.m.Hartford Bradley Intl
6h 43m
1 stop
YWG10:33 p.m.Winnipeg
14 Aug
YWG7:00 a.m.Winnipeg
15h 59m
2 stops
BDL11:59 p.m.Hartford Bradley Intl
C$ 1,037

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 27 June 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 16/9

10:05 a.m.-5:15 p.m.

1 stop8h 10m

Winnipeg

Wed 23/9

11:15 a.m.-9:05 a.m.

2 stops20h 50m

C$ 477

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 16/9

7:30 p.m.-12:55 a.m.

1 stop6h 25m

Winnipeg

Wed 23/9

6:05 p.m.-9:05 a.m.

1 stop14h 00m

C$ 485

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 30/10

8:00 a.m.-6:10 p.m.

2 stops11h 10m

Winnipeg

Mon 2/11

7:05 p.m.-12:32 p.m.

1 stop16h 27m

C$ 490

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 23/9

10:05 a.m.-5:15 p.m.

1 stop8h 10m

Winnipeg

Wed 30/9

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

2 stops30h 20m

C$ 495

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 28/8

7:30 p.m.-12:55 a.m.

1 stop6h 25m

Winnipeg

Mon 31/8

11:15 a.m.-9:05 a.m.

2 stops20h 50m

C$ 501

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 13/7

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

1 stop6h 14m

Winnipeg

Mon 27/7

12:15 p.m.-6:35 p.m.

1 stop5h 20m

C$ 504

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Wed 2/9

6:50 a.m.-3:08 p.m.

1 stop9h 18m

Winnipeg

Mon 7/9

10:45 a.m.-11:51 p.m.

2 stops12h 06m

C$ 998

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Tue 11/8

5:30 a.m.-12:55 a.m.

2 stops20h 25m

Winnipeg

Fri 14/8

7:00 a.m.-11:25 p.m.

2 stops15h 25m

C$ 999
Quickest round-trip

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Tue 11/8

6:50 a.m.-11:54 a.m.

1 stop6h 04m

Winnipeg

Fri 14/8

5:42 p.m.-11:25 p.m.

1 stop4h 43m

C$ 1,009

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Sun 20/9

6:00 a.m.-10:33 p.m.

2 stops17h 33m

Winnipeg

Wed 23/9

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

1 stop6h 29m

C$ 1,023

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$ 158, 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 March is also very affordable. Most momondo users find prices during this month for around C$ 160.

Can stopping save me money on Massachusetts to Winnipeg flights?

You could potentially save up to 42% 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.
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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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