Cheap flights from Massachusetts to Winnipeg from C$ 191

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 22/9. 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

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Find the cheapest flights from Massachusetts to Winnipeg

Cheap round-trip flights

WestJet Logo
7:00 p.m. - 2:13 p.m.BOS-YWG
20h 13m1 stop
WestJet Logo
6:30 a.m. - 5:40 p.m.YWG-BOS
10h 10m1 stop
C$ 429WestJet
Find Deal
sáb, 27 set - sáb, 4 out
WestJet Logo
7:00 p.m. - 2:13 p.m.BOS-YWG
20h 13m1 stop
WestJet Logo
6:15 p.m. - 6:10 p.m.YWG-BOS
22h 55m2 stops
C$ 431WestJet
Find Deal
sáb, 27 set - sáb, 4 out
 Logo
10:40 a.m. - 11:41 a.m.BOS-YWG
26h 01m2 stops
 Logo
3:15 p.m. - 9:30 a.m.YWG-BOS
17h 15m2 stops
C$ 487
Find Deal
qui, 25 set - qua, 1 out
Air Canada Logo
6:00 a.m. - 10:40 a.m.BOS-YWG
5h 40m1 stop
Air Canada Logo
7:55 a.m. - 2:30 p.m.YWG-BOS
5h 35m1 stop
C$ 505Air Canada
Find Deal
qui, 25 set - qua, 1 out
Air Canada Logo
6:00 a.m. - 1:56 p.m.BOS-YWG
8h 56m2 stops
Air Canada Logo
7:55 a.m. - 2:30 p.m.YWG-BOS
5h 35m1 stop
C$ 510Air Canada
Find Deal
qui, 25 set - qua, 1 out
 Logo
12:20 p.m. - 4:22 p.m.BOS-YWG
29h 02m3 stops
 Logo
9:05 p.m. - 10:52 p.m.YWG-BOS
24h 47m3 stops
C$ 521
Find Deal
qua, 10 set - seg, 13 out
Porter Airlines Logo
6:55 p.m. - 11:13 a.m.BOS-YWG
17h 18m2 stops
Porter Airlines Logo
12:10 p.m. - 10:05 p.m.YWG-BOS
8h 55m1 stop
C$ 588Porter Airlines
Find Deal
sex, 14 nov - ter, 18 nov
United Airlines Logo
4:27 p.m. - 10:33 p.m.BOS-YWG
7h 06m1 stop
United Airlines Logo
4:25 p.m. - 6:00 a.m.YWG-BOS
12h 35m1 stop
C$ 606United Airlines
Find Deal
sex, 19 set - sex, 26 set
Porter Airlines Logo
6:55 p.m. - 3:30 p.m.BOS-YWG
21h 35m1 stop
Porter Airlines Logo
12:10 p.m. - 10:05 p.m.YWG-BOS
8h 55m1 stop
C$ 612Porter Airlines
Find Deal
sex, 14 nov - ter, 18 nov
United Airlines Logo
6:00 a.m. - 5:45 p.m.BDL-YWG
12h 45m2 stops
United Airlines Logo
5:00 a.m. - 11:37 p.m.YWG-BDL
17h 37m2 stops
C$ 904United Airlines
Find Deal
dom, 12 out - dom, 19 out

Air Canada flights from Massachusetts to Winnipeg

Our best Air Canada deals on Massachusetts to Winnipeg flight tickets
Air Canada
25 Sep
BOS6:00 a.m.Boston Logan Intl
5h 40m
1 stop
YWG10:40 a.m.Winnipeg
1 Oct
YWG7:55 a.m.Winnipeg
5h 35m
1 stop
BOS2:30 p.m.Boston Logan Intl
Air Canada
25 Sep
BOS6:00 a.m.Boston Logan Intl
8h 56m
2 stops
YWG1:56 p.m.Winnipeg
1 Oct
YWG7:55 a.m.Winnipeg
5h 35m
1 stop
BOS2:30 p.m.Boston Logan Intl
Air Canada
14 Jan
BOS10:15 a.m.Boston Logan Intl
7h 20m
1 stop
YWG4:35 p.m.Winnipeg
21 Jan
YWG8:15 a.m.Winnipeg
5h 37m
1 stop
BOS2:52 p.m.Boston Logan Intl

Delta flights from Massachusetts to Winnipeg

Our best Delta deals on Massachusetts to Winnipeg flight tickets
Delta
23 Sep
BOS5:40 a.m.Boston Logan Intl
12h 10m
2 stops
YWG4:50 p.m.Winnipeg
24 Sep
YWG5:40 p.m.Winnipeg
5h 19m
1 stop
BOS11:59 p.m.Boston Logan Intl
Delta
14 Jan
BOS9:10 a.m.Boston Logan Intl
8h 50m
2 stops
YWG5:00 p.m.Winnipeg
21 Jan
YWG5:38 p.m.Winnipeg
5h 21m
1 stop
BOS11:59 p.m.Boston Logan Intl
Delta
14 Jan
BOS5:30 a.m.Boston Logan Intl
12h 30m
2 stops
YWG5:00 p.m.Winnipeg
21 Jan
YWG6:40 a.m.Winnipeg
10h 10m
2 stops
BOS5:50 p.m.Boston Logan Intl

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 28 agosto 2025.
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

sáb 27/9

7:00 p.m.-2:13 p.m.

1 stop20h 13m

Winnipeg

sáb 4/10

6:30 a.m.-5:40 p.m.

1 stop10h 10m

C$ 429

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

sáb 27/9

7:00 p.m.-2:13 p.m.

1 stop20h 13m

Winnipeg

sáb 4/10

6:15 p.m.-6:10 p.m.

2 stops22h 55m

C$ 431

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

qui 25/9

10:40 a.m.-11:41 a.m.

2 stops26h 01m

Winnipeg

qua 1/10

3:15 p.m.-9:30 a.m.

2 stops17h 15m

C$ 487

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

qui 25/9

6:00 a.m.-10:40 a.m.

1 stop5h 40m

Winnipeg

qua 1/10

7:55 a.m.-2:30 p.m.

1 stop5h 35m

C$ 505

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

qui 25/9

6:00 a.m.-1:56 p.m.

2 stops8h 56m

Winnipeg

qua 1/10

7:55 a.m.-2:30 p.m.

1 stop5h 35m

C$ 510

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

qua 10/9

12:20 p.m.-4:22 p.m.

3 stops29h 02m

Winnipeg

seg 13/10

9:05 p.m.-10:52 p.m.

3 stops24h 47m

C$ 521

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

sex 14/11

6:55 p.m.-11:13 a.m.

2 stops17h 18m

Winnipeg

ter 18/11

12:10 p.m.-10:05 p.m.

1 stop8h 55m

C$ 588

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

sex 19/9

4:27 p.m.-10:33 p.m.

1 stop7h 06m

Winnipeg

sex 26/9

4:25 p.m.-6:00 a.m.

1 stop12h 35m

C$ 606

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

sex 14/11

6:55 p.m.-3:30 p.m.

1 stop21h 35m

Winnipeg

ter 18/11

12:10 p.m.-10:05 p.m.

1 stop8h 55m

C$ 612

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

dom 12/10

6:00 a.m.-5:45 p.m.

2 stops12h 45m

Winnipeg

dom 19/10

5:00 a.m.-11:37 p.m.

2 stops17h 37m

C$ 904

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 July. Flight prices, which tend to average around C$ 322, 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 May is also very affordable. Most momondo users find prices during this month for around C$ 453.

What is the cheapest day to depart on your flight to Winnipeg?

Our data shows that Wednesday is the least expensive day to fly to Winnipeg. Tickets to fly out on this day can be as low as C$ 621. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Thursday is C$ 836.

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$ 614 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$ 465 on momondo.

Cheap Massachusetts to Winnipeg flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Winnipeg

Direct flights

None
There are no direct flights from Massachusetts to Winnipeg. There are no popular flight routes 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
Selkirk
Morden
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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1 adult
ter 2/9
ter 9/9

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