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Cheap flights from Winnipeg to Massachusetts from C$ 324

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 24/1. 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:30 a.m. - 8:49 p.m.YWG-BOS
12h 19m1 stop
Multiple Airlines Logo
9:54 p.m. - 12:41 a.m.BOS-YWG
27h 47m2 stops
C$ 404Multiple Airlines
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Air Canada Logo
5:30 a.m. - 12:12 p.m.YWG-BOS
5h 42m1 stop
Air Canada Logo
5:30 a.m. - 10:16 a.m.BOS-YWG
5h 46m1 stop
C$ 438Air Canada
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Multiple Airlines Logo
7:30 a.m. - 11:53 p.m.YWG-BOS
15h 23m2 stops
Multiple Airlines Logo
9:54 p.m. - 8:06 p.m.BOS-YWG
23h 12m3 stops
C$ 442Multiple Airlines
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Multiple Airlines Logo
5:00 a.m. - 2:55 p.m.YWG-BOS
8h 55m1 stop
Multiple Airlines Logo
9:54 p.m. - 3:07 p.m.BOS-YWG
18h 13m2 stops
C$ 445Multiple Airlines
Find Deal
Tue, 25 Nov - Tue, 2 Dec
Multiple Airlines Logo
7:30 a.m. - 8:49 p.m.YWG-BOS
12h 19m1 stop
Multiple Airlines Logo
9:54 p.m. - 8:06 p.m.BOS-YWG
23h 12m3 stops
C$ 453Multiple Airlines
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Multiple Airlines Logo
8:20 p.m. - 9:35 a.m.YWG-BOS
12h 15m1 stop
Multiple Airlines Logo
9:54 p.m. - 3:07 p.m.BOS-YWG
18h 13m2 stops
C$ 455Multiple Airlines
Find Deal
Mon, 24 Nov - Tue, 2 Dec
Air Canada Logo
7:05 p.m. - 9:57 a.m.YWG-BOS
13h 52m1 stop
Air Canada Logo
5:30 a.m. - 10:16 a.m.BOS-YWG
5h 46m1 stop
C$ 470Air Canada
Find Deal
Mon, 24 Nov - Tue, 2 Dec
United Airlines Logo
2:15 p.m. - 9:06 p.m.YWG-ALB
5h 51m1 stop
United Airlines Logo
6:15 a.m. - 11:39 a.m.ALB-YWG
6h 24m1 stop
C$ 628United Airlines
Find Deal
Wed, 25 Mar - Thu, 26 Mar
United Airlines Logo
2:15 p.m. - 9:06 p.m.YWG-ALB
5h 51m1 stop
United Airlines Logo
6:15 a.m. - 11:39 a.m.ALB-YWG
6h 24m1 stop
C$ 629United Airlines
Find Deal
Wed, 25 Mar - Thu, 26 Mar
Delta Logo
5:45 p.m. - 12:06 a.m.YWG-BOS
5h 21m1 stop
Delta Logo
3:15 p.m. - 11:44 p.m.BOS-YWG
9h 29m1 stop
C$ 765Delta
Find Deal
Fri, 19 Dec - Mon, 22 Dec

Air Canada flights from Winnipeg to Massachusetts

Our best Air Canada deals on Winnipeg to Massachusetts flight tickets
Air Canada
26 Nov
YWG5:30 a.m.Winnipeg
5h 42m
1 stop
BOS12:12 p.m.Boston Logan Intl
3 Dec
BOS5:30 a.m.Boston Logan Intl
5h 46m
1 stop
YWG10:16 a.m.Winnipeg
C$ 438
Find similar
Air Canada
24 Nov
YWG7:05 p.m.Winnipeg
13h 52m
1 stop
BOS9:57 a.m.Boston Logan Intl
2 Dec
BOS5:30 a.m.Boston Logan Intl
5h 46m
1 stop
YWG10:16 a.m.Winnipeg
C$ 470
Find similar
Air Canada
10 Dec
YWG8:15 a.m.Winnipeg
5h 37m
1 stop
BOS2:52 p.m.Boston Logan Intl
17 Dec
BOS5:30 a.m.Boston Logan Intl
5h 46m
1 stop
YWG10:16 a.m.Winnipeg
C$ 579
Find similar

United Airlines flights from Winnipeg to Massachusetts

Our best United Airlines deals on Winnipeg to Massachusetts flight tickets
United Airlines
25 Mar
YWG2:15 p.m.Winnipeg
5h 51m
1 stop
ALB9:06 p.m.Albany Intl
26 Mar
ALB6:15 a.m.Albany Intl
6h 24m
1 stop
YWG11:39 a.m.Winnipeg
C$ 628
Find similar
United Airlines
25 Mar
YWG2:15 p.m.Winnipeg
5h 51m
1 stop
ALB9:06 p.m.Albany Intl
26 Mar
ALB6:15 a.m.Albany Intl
6h 24m
1 stop
YWG11:39 a.m.Winnipeg
C$ 629
Find similar
United Airlines
25 Mar
YWG5:30 a.m.Winnipeg
17h 46m
2 stops
ALB12:16 a.m.Albany Intl
26 Mar
ALB6:15 a.m.Albany Intl
6h 24m
1 stop
YWG11:39 a.m.Winnipeg
C$ 712
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 28 October 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

Wed 26/11

7:30 a.m.-8:49 p.m.

1 stop12h 19m

Boston Logan Intl

Wed 3/12

9:54 p.m.-12:41 a.m.

2 stops27h 47m

C$ 404

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 26/11

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

1 stop5h 42m

Boston Logan Intl

Wed 3/12

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

1 stop5h 46m

C$ 438

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 26/11

7:30 a.m.-11:53 p.m.

2 stops15h 23m

Boston Logan Intl

Wed 3/12

9:54 p.m.-8:06 p.m.

3 stops23h 12m

C$ 442

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 25/11

5:00 a.m.-2:55 p.m.

1 stop8h 55m

Boston Logan Intl

Tue 2/12

9:54 p.m.-3:07 p.m.

2 stops18h 13m

C$ 445

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 26/11

7:30 a.m.-8:49 p.m.

1 stop12h 19m

Boston Logan Intl

Wed 3/12

9:54 p.m.-8:06 p.m.

3 stops23h 12m

C$ 453

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 24/11

8:20 p.m.-9:35 a.m.

1 stop12h 15m

Boston Logan Intl

Tue 2/12

9:54 p.m.-3:07 p.m.

2 stops18h 13m

C$ 455

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 24/11

7:05 p.m.-9:57 a.m.

1 stop13h 52m

Boston Logan Intl

Tue 2/12

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

1 stop5h 46m

C$ 470

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Wed 25/3

2:15 p.m.-9:06 p.m.

1 stop5h 51m

Albany Intl

Thu 26/3

6:15 a.m.-11:39 a.m.

1 stop6h 24m

C$ 628

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Wed 25/3

2:15 p.m.-9:06 p.m.

1 stop5h 51m

Albany Intl

Thu 26/3

6:15 a.m.-11:39 a.m.

1 stop6h 24m

C$ 629

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 19/12

5:45 p.m.-12:06 a.m.

1 stop5h 21m

Boston Logan Intl

Mon 22/12

3:15 p.m.-11:44 p.m.

1 stop9h 29m

C$ 765

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 June. Flight prices, which tend to average around C$ 445, are often lower during this time because this is during the off-season. If you are unable to visit Massachusetts during the month of June, then departing from Winnipeg during the month August 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$ 431. 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$ 629.

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$ 543. In contrast, the most expensive time of day to depart to Massachusetts is in the afternoon when prices are around C$ 657.

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$ 568 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$ 338 on momondo.

Can stopping save me money on Winnipeg to Massachusetts flights?

You could potentially save up to 15% 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

Direct flights

None
There are no direct flights from Winnipeg to Massachusetts. There are no popular flight routes from Winnipeg to Massachusetts.
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$ 241Free CancellationRating
7.4
8,996 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 348Free CancellationRating
7.1
10,370 reviews
Search Air Canada flights
Porter AirlinesPriceFrom C$ 428Free CancellationRating
8.0
384 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 479Free CancellationRating
7.2
3,148 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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