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Cheap flights from Winnipeg to Massachusetts from C$ 258

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Massachusetts departing on 2/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Winnipeg to Massachusetts

Cheap round-trip flights

WestJet Logo
6:30 a.m. - 5:40 p.m.YWG-BOS
10h 10m1 stop
WestJet Logo
6:30 p.m. - 11:41 a.m.BOS-YWG
18h 11m1 stop
C$ 362WestJet
Find Deal
ven., 19 sept. - ven., 26 sept.
Logo
7:40 a.m. - 7:00 p.m.YWG-BOS
10h 20m1 stop
Logo
12:20 p.m. - 2:19 p.m.BOS-YWG
26h 59m1 stop
C$ 375
Find Deal
lun., 27 oct. - jeu., 30 oct.
WestJet Logo
8:15 p.m. - 6:10 p.m.YWG-BOS
20h 55m1 stop
WestJet Logo
7:00 p.m. - 2:13 p.m.BOS-YWG
20h 13m1 stop
C$ 384WestJet
Find Deal
ven., 12 sept. - lun., 15 sept.
Air Canada Logo
5:00 a.m. - 11:29 a.m.YWG-BOS
5h 29m1 stop
Air Canada Logo
5:30 a.m. - 10:16 a.m.BOS-YWG
5h 46m1 stop
C$ 412Air Canada
Find Deal
ven., 24 oct. - lun., 27 oct.
United Airlines Logo
7:00 a.m. - 11:59 p.m.YWG-BOS
15h 59m2 stops
United Airlines Logo
7:10 a.m. - 3:31 p.m.BOS-YWG
9h 21m2 stops
C$ 466United Airlines
Find Deal
dim., 31 août - jeu., 4 sept.
Air Canada Logo
5:00 a.m. - 11:26 a.m.YWG-BOS
5h 26m1 stop
Air Canada Logo
6:00 a.m. - 10:40 a.m.BOS-YWG
5h 40m1 stop
C$ 467Air Canada
Find Deal
dim., 31 août - jeu., 4 sept.
Delta Logo
12:20 p.m. - 10:04 p.m.YWG-BOS
8h 44m1 stop
Delta Logo
11:37 a.m. - 8:10 p.m.BOS-YWG
9h 33m1 stop
C$ 490Delta
Find Deal
mar., 7 oct. - mer., 15 oct.
Delta Logo
5:41 p.m. - 12:18 a.m.YWG-BOS
5h 37m1 stop
Delta Logo
5:34 a.m. - 11:51 a.m.BOS-YWG
7h 17m1 stop
C$ 565Delta
Find Deal
mer., 27 août - mer., 3 sept.
United Airlines Logo
2:20 p.m. - 10:35 a.m.YWG-BOS
19h 15m2 stops
United Airlines Logo
1:38 p.m. - 10:33 p.m.BOS-YWG
9h 55m2 stops
C$ 566United Airlines
Find Deal
mer., 27 août - mer., 3 sept.
Porter Airlines Logo
11:20 a.m. - 10:01 p.m.YWG-BOS
9h 41m2 stops
Porter Airlines Logo
3:30 p.m. - 11:35 p.m.BOS-YWG
9h 05m2 stops
C$ 573Porter Airlines
Find Deal
ven., 24 oct. - lun., 27 oct.

WestJet flights from Winnipeg to Massachusetts

Our best WestJet deals on Winnipeg to Massachusetts flight tickets
WestJet
19 Sep
YWG6:30 a.m.Winnipeg
10h 10m
1 stop
BOS5:40 p.m.Boston Logan Intl
26 Sep
BOS6:30 p.m.Boston Logan Intl
18h 11m
1 stop
YWG11:41 a.m.Winnipeg
C$ 362
Find similar
WestJet
12 Sep
YWG8:15 p.m.Winnipeg
20h 55m
1 stop
BOS6:10 p.m.Boston Logan Intl
15 Sep
BOS7:00 p.m.Boston Logan Intl
20h 13m
1 stop
YWG2:13 p.m.Winnipeg
C$ 384
Find similar
WestJet
19 Sep
YWG6:30 a.m.Winnipeg
10h 10m
1 stop
BOS5:40 p.m.Boston Logan Intl
26 Sep
BOS7:00 p.m.Boston Logan Intl
23h 25m
2 stops
YWG5:25 p.m.Winnipeg
C$ 393
Find similar

United Airlines flights from Winnipeg to Massachusetts

Our best United Airlines deals on Winnipeg to Massachusetts flight tickets
United Airlines
31 Aug
YWG7:00 a.m.Winnipeg
15h 59m
2 stops
BOS11:59 p.m.Boston Logan Intl
4 Sep
BOS7:10 a.m.Boston Logan Intl
9h 21m
2 stops
YWG3:31 p.m.Winnipeg
C$ 466
Find similar
United Airlines
27 Aug
YWG2:20 p.m.Winnipeg
19h 15m
2 stops
BOS10:35 a.m.Boston Logan Intl
3 Sep
BOS1:38 p.m.Boston Logan Intl
9h 55m
2 stops
YWG10:33 p.m.Winnipeg
C$ 566
Find similar
United Airlines
27 Oct
YWG8:40 a.m.Winnipeg
15h 05m
2 stops
BOS12:45 a.m.Boston Logan Intl
30 Oct
BOS9:30 a.m.Boston Logan Intl
27h 27m
2 stops
YWG11:57 a.m.Winnipeg
C$ 612
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Massachusetts 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 5 août 2025.
Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

ven. 19/9

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

1 stop10h 10m

Boston Logan Intl

ven. 26/9

6:30 p.m.-11:41 a.m.

1 stop18h 11m

C$ 362

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

lun. 27/10

7:40 a.m.-7:00 p.m.

1 stop10h 20m

Boston Logan Intl

jeu. 30/10

12:20 p.m.-2:19 p.m.

1 stop26h 59m

C$ 375

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

ven. 12/9

8:15 p.m.-6:10 p.m.

1 stop20h 55m

Boston Logan Intl

lun. 15/9

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

1 stop20h 13m

C$ 384

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

ven. 24/10

5:00 a.m.-11:29 a.m.

1 stop5h 29m

Boston Logan Intl

lun. 27/10

5:30 a.m.-10:16 a.m.

1 stop5h 46m

C$ 412

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

dim. 31/8

7:00 a.m.-11:59 p.m.

2 stops15h 59m

Boston Logan Intl

jeu. 4/9

7:10 a.m.-3:31 p.m.

2 stops9h 21m

C$ 466

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

dim. 31/8

5:00 a.m.-11:26 a.m.

1 stop5h 26m

Boston Logan Intl

jeu. 4/9

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

1 stop5h 40m

C$ 467

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mar. 7/10

12:20 p.m.-10:04 p.m.

1 stop8h 44m

Boston Logan Intl

mer. 15/10

11:37 a.m.-8:10 p.m.

1 stop9h 33m

C$ 490

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mer. 27/8

5:41 p.m.-12:18 a.m.

1 stop5h 37m

Boston Logan Intl

mer. 3/9

5:34 a.m.-11:51 a.m.

1 stop7h 17m

C$ 565

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mer. 27/8

2:20 p.m.-10:35 a.m.

2 stops19h 15m

Boston Logan Intl

mer. 3/9

1:38 p.m.-10:33 p.m.

2 stops9h 55m

C$ 566

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

ven. 24/10

11:20 a.m.-10:01 p.m.

2 stops9h 41m

Boston Logan Intl

lun. 27/10

3:30 p.m.-11:35 p.m.

2 stops9h 05m

C$ 573

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 Massachusetts from

How to get the cheapest flight ticket from Winnipeg to Massachusetts

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 Massachusetts?

The cheapest month to fly to Massachusetts from Winnipeg is in October. Flight prices, which tend to average around C$ 406, are often lower during this time because this is during the off-season. If you are unable to visit Massachusetts during the month of October, then departing from Winnipeg during the month September is also very affordable. Most momondo users find prices during this month for around C$ 448.

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

On average, the least expensive day to fly to Massachusetts from Winnipeg is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as C$ 425. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Massachusetts for around C$ 620.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our most recent data shows that the best time of day to fly to Massachusetts is in the morning. Flights from Winnipeg to Massachusetts during this time can be as low as C$ 535. In contrast, the most expensive time of day to depart to Massachusetts is in the afternoon when prices are around C$ 647.

How far in advance should I book a flight to Massachusetts?

You are more likely to see cheaper flights to Massachusetts from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around C$ 550 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Winnipeg for as low as C$ 333 on momondo.

Can stopping save me money on Winnipeg to Massachusetts flights?

You could potentially save up to 9% on your flight if you consider stops on a Winnipeg to Massachusetts flight.

Cheap Winnipeg to Massachusetts flight deals and tips

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

Best price found

C$ 258

Fastest flight time

5h 26m

Direct flights

None

Airports in Massachusetts

2 airports
The best one-way flight to Massachusetts from Winnipeg in the past 72 hours is C$ 258. The best round-trip flight deal from Winnipeg to Massachusetts found on momondo in the last 72 hours is C$ 362.
The fastest flight from Winnipeg to Massachusetts takes 5h 26m
There are no direct flights from Winnipeg to Massachusetts. Popular non-direct route for this connection is Winnipeg Airport - Boston Logan Intl Airport.
There are 2 airports near Massachusetts: Boston Logan Intl (BOS), Albany Intl (ALB)
Search flight deals

  • When did momondo last update prices for flights from Winnipeg Airport to Massachusetts?

    Prices for flights from Winnipeg Airport to Massachusetts are refreshed on a daily basis.

  • How many operators does momondo search for flights from Winnipeg Airport to Massachusetts?

  • How old do you have to be to fly from Winnipeg Airport to Massachusetts?

    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 Winnipeg Airport to Massachusetts.

  • What documentation or ID do you need to fly to Massachusetts?

    The travel and health documents you'll need for your trip to Massachusetts may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Massachusetts. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Winnipeg to Massachusetts

Compare and see reviews for airlines that fly from Winnipeg to Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom C$ 238Free CancellationRating
7.4
8,916 reviews
Search United Airlines flights
Porter AirlinesPriceFrom C$ 318Free CancellationRating
8.0
322 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 336Free CancellationRating
7.1
9,890 reviews
Search Air Canada flights
DeltaPriceFrom C$ 366Free CancellationRating
8.0
7,985 reviews
Search Delta flights
WestJetPriceFrom C$ 472Free CancellationRating
7.2
2,997 reviews
Search WestJet flights

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Massachusetts?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Winnipeg to Massachusetts for you.

Can I find flights from Winnipeg to Massachusetts with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Winnipeg to Massachusetts flights to just show those with flexible booking policies.

How can momondo help me find flights from Winnipeg to Massachusetts?

Once you have performed a search for Winnipeg to Massachusetts flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Winnipeg to Massachusetts right now. Can momondo alert me if prices change?

Price alerts on flights to Massachusetts from Winnipeg are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Massachusetts trip

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