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Cheap flights from Massachusetts to Winnipeg from C$ 156

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 16/5. 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.
Multiple Airlines Logo
4:45 p.m. - 12:55 a.m.
BOS
-
YWG
9h 10m
1 stop
Multiple Airlines Logo
9:05 p.m. - 11:45 a.m.
YWG
-
BOS
13h 40m
2 stops
C$ 420Multiple Airlines
Sun, 3 May - Thu, 7 May
Air Canada Logo
10:35 a.m. - 3:04 p.m.
BOS
-
YWG
5h 29m
1 stop
Air Canada Logo
11:00 a.m. - 6:07 p.m.
YWG
-
BOS
6h 07m
1 stop
C$ 428Air Canada
Thu, 14 May - Mon, 18 May
Multiple Airlines Logo
5:40 a.m. - 12:55 a.m.
BOS
-
YWG
20h 15m
2 stops
Multiple Airlines Logo
6:00 a.m. - 3:50 p.m.
YWG
-
BOS
8h 50m
1 stop
C$ 472Multiple Airlines
Thu, 14 May - Mon, 18 May
WestJet Logo
6:00 a.m. - 4:51 p.m.
BDL
-
YWG
11h 51m
1 stop
WestJet Logo
6:00 a.m. - 11:32 p.m.
YWG
-
BDL
16h 32m
2 stops
C$ 599WestJet
Sun, 31 May - Sun, 7 Jun
WestJet Logo
9:37 a.m. - 5:15 p.m.
BDL
-
YWG
8h 38m
2 stops
WestJet Logo
7:00 a.m. - 11:32 p.m.
YWG
-
BDL
15h 32m
2 stops
C$ 613WestJet
Sun, 31 May - Sun, 7 Jun
WestJet Logo
6:00 a.m. - 4:51 p.m.
BDL
-
YWG
11h 51m
1 stop
WestJet Logo
4:09 p.m. - 11:32 p.m.
YWG
-
BDL
6h 23m
1 stop
C$ 626WestJet
Sun, 31 May - Sun, 7 Jun
United Airlines Logo
6:00 a.m. - 11:57 a.m.
ALB
-
YWG
6h 57m
1 stop
United Airlines Logo
5:30 a.m. - 9:04 p.m.
YWG
-
ALB
14h 34m
2 stops
C$ 704United Airlines
Thu, 26 Feb - Mon, 2 Mar
Delta Logo
6:05 a.m. - 11:01 a.m.
BDL
-
YWG
5h 56m
1 stop
Delta Logo
5:19 p.m. - 11:21 p.m.
YWG
-
BDL
5h 02m
1 stop
C$ 753Delta
Thu, 19 Feb - Mon, 23 Feb
Delta Logo
5:35 a.m. - 4:27 p.m.
ALB
-
YWG
11h 52m
2 stops
Delta Logo
11:53 a.m. - 11:02 p.m.
YWG
-
ALB
10h 09m
2 stops
C$ 845Delta
Thu, 26 Feb - Thu, 5 Mar
United Airlines Logo
6:00 a.m. - 11:57 a.m.
ALB
-
YWG
6h 57m
1 stop
United Airlines Logo
2:20 p.m. - 12:30 a.m.
YWG
-
ALB
9h 10m
1 stop
C$ 916United Airlines
Thu, 26 Feb - Thu, 5 Mar

Delta flights from Massachusetts to Winnipeg

Our best Delta deals on Massachusetts to Winnipeg flight tickets
Delta
19 Feb
BDL6:05 a.m.Hartford Bradley Intl
5h 56m
1 stop
YWG11:01 a.m.Winnipeg
23 Feb
YWG5:19 p.m.Winnipeg
5h 02m
1 stop
BDL11:21 p.m.Hartford Bradley Intl
C$ 753
Delta
26 Feb
ALB5:35 a.m.Albany Intl
11h 52m
2 stops
YWG4:27 p.m.Winnipeg
5 Mar
YWG11:53 a.m.Winnipeg
10h 09m
2 stops
ALB11:02 p.m.Albany Intl
C$ 845
Delta
19 Feb
BOS5:50 a.m.Boston Logan Intl
6h 11m
1 stop
YWG11:01 a.m.Winnipeg
20 Feb
YWG5:19 p.m.Winnipeg
5h 31m
1 stop
BOS11:50 p.m.Boston Logan Intl
C$ 1,786

American Airlines flights from Massachusetts to Winnipeg

Our best American Airlines deals on Massachusetts to Winnipeg flight tickets
American Airlines
19 Feb
BDL5:33 p.m.Hartford Bradley Intl
31h 02m
3 stops
YWG11:35 p.m.Winnipeg
23 Feb
YWG12:10 p.m.Winnipeg
21h 58m
2 stops
BDL11:08 a.m.Hartford Bradley Intl
C$ 1,309
American Airlines
26 Feb
ALB5:28 p.m.Albany Intl
31h 07m
3 stops
YWG11:35 p.m.Winnipeg
5 Mar
YWG12:10 p.m.Winnipeg
25h 58m
2 stops
ALB3:08 p.m.Albany Intl
C$ 1,425
American Airlines
12 Feb
BOS11:00 a.m.Boston Logan Intl
13h 35m
2 stops
YWG11:35 p.m.Winnipeg
16 Feb
YWG6:00 a.m.Winnipeg
16h 23m
2 stops
BOS11:23 p.m.Boston Logan Intl
C$ 1,564

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 6 February 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

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 3/5

4:45 p.m.-12:55 a.m.

1 stop9h 10m

Winnipeg

Thu 7/5

9:05 p.m.-11:45 a.m.

2 stops13h 40m

C$ 420

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 14/5

10:35 a.m.-3:04 p.m.

1 stop5h 29m

Winnipeg

Mon 18/5

11:00 a.m.-6:07 p.m.

1 stop6h 07m

C$ 428

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 14/5

5:40 a.m.-12:55 a.m.

2 stops20h 15m

Winnipeg

Mon 18/5

6:00 a.m.-3:50 p.m.

1 stop8h 50m

C$ 472

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Sun 31/5

6:00 a.m.-4:51 p.m.

1 stop11h 51m

Winnipeg

Sun 7/6

6:00 a.m.-11:32 p.m.

2 stops16h 32m

C$ 599

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Sun 31/5

9:37 a.m.-5:15 p.m.

2 stops8h 38m

Winnipeg

Sun 7/6

7:00 a.m.-11:32 p.m.

2 stops15h 32m

C$ 613

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Sun 31/5

6:00 a.m.-4:51 p.m.

1 stop11h 51m

Winnipeg

Sun 7/6

4:09 p.m.-11:32 p.m.

1 stop6h 23m

C$ 626

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Thu 26/2

6:00 a.m.-11:57 a.m.

1 stop6h 57m

Winnipeg

Mon 2/3

5:30 a.m.-9:04 p.m.

2 stops14h 34m

C$ 704

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Thu 19/2

6:05 a.m.-11:01 a.m.

1 stop5h 56m

Winnipeg

Mon 23/2

5:19 p.m.-11:21 p.m.

1 stop5h 02m

C$ 753

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Thu 26/2

5:35 a.m.-4:27 p.m.

2 stops11h 52m

Winnipeg

Thu 5/3

11:53 a.m.-11:02 p.m.

2 stops10h 09m

C$ 845

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Thu 26/2

6:00 a.m.-11:57 a.m.

1 stop6h 57m

Winnipeg

Thu 5/3

2:20 p.m.-12:30 a.m.

1 stop9h 10m

C$ 916

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 July. Flight prices, which tend to average around C$ 319, 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 March is also very affordable. Most momondo users find prices during this month for around C$ 429.

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$ 598 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$ 272 on momondo.

Can stopping save me money on Massachusetts to Winnipeg flights?

You could potentially save up to 1% 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 11m

Direct flights

None
The fastest flight from Massachusetts to Winnipeg takes 6h 11m
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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