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Cheap flights from Massachusetts to Winnipeg from $166

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 2/5. 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
0 bags

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Cheap round-trip flights

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Multiple Airlines Logo
9:00 am - 7:09 pmBOS-YWG
11h 09m1 stop
Multiple Airlines Logo
7:30 am - 1:04 amYWG-BOS
16h 34m1 stop
$373Multiple Airlines
Find Deal
Thu, Feb 5 - Fri, Feb 6
Air Canada Logo
5:30 am - 10:16 amBOS-YWG
5h 46m1 stop
Air Canada Logo
5:30 am - 12:12 pmYWG-BOS
5h 42m1 stop
$387Air Canada
Find Deal
Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
7:00 am - 11:32 amBOS-YWG
29h 32m2 stops
Multiple Airlines Logo
8:20 pm - 11:05 amYWG-BOS
13h 45m1 stop
$416Multiple Airlines
Find Deal
Thu, Feb 5 - Fri, Feb 6
Multiple Airlines Logo
7:00 am - 11:32 amBOS-YWG
29h 32m2 stops
Multiple Airlines Logo
8:20 pm - 11:15 pmYWG-BOS
25h 55m2 stops
$441Multiple Airlines
Find Deal
Thu, Feb 5 - Fri, Feb 6
Multiple Airlines Logo
3:43 pm - 11:32 amBOS-YWG
20h 49m2 stops
Multiple Airlines Logo
2:40 pm - 11:15 pmYWG-BOS
31h 35m3 stops
$451Multiple Airlines
Find Deal
Thu, Feb 5 - Fri, Feb 6
Air Canada Logo
10:15 am - 4:35 pmBOS-YWG
7h 20m1 stop
Air Canada Logo
8:15 am - 2:52 pmYWG-BOS
5h 37m1 stop
$552Air Canada
Find Deal
Tue, Feb 24 - Thu, Feb 26
American Airlines Logo
6:00 am - 11:35 pmBOS-YWG
18h 35m2 stops
American Airlines Logo
6:00 am - 4:37 pmYWG-BOS
9h 37m2 stops
$640American Airlines
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Tue, Dec 23 - Tue, Dec 30
United Airlines Logo
6:01 am - 11:57 amBOS-YWG
6h 56m1 stop
United Airlines Logo
2:20 pm - 12:45 amYWG-BOS
9h 25m1 stop
$650United Airlines
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Mon, Dec 22 - Tue, Dec 30
Porter Airlines Logo
1:25 pm - 11:35 pmBOS-YWG
11h 10m1 stop
Porter Airlines Logo
6:00 am - 10:05 pmYWG-BOS
15h 05m1 stop
$673Porter Airlines
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Tue, Dec 23 - Mon, Dec 29
American Airlines Logo
2:04 pm - 11:35 pmBOS-YWG
10h 31m2 stops
American Airlines Logo
6:00 am - 8:26 pmYWG-BOS
13h 26m2 stops
$715American Airlines
Find Deal
Tue, Dec 23 - Tue, Dec 30

American Airlines flights from Massachusetts to Winnipeg

Our best American Airlines deals on Massachusetts to Winnipeg flight tickets
American Airlines
Dec 23
BOS6:00 amBoston Logan Intl
18h 35m
2 stops
YWG11:35 pmWinnipeg
Dec 30
YWG6:00 amWinnipeg
9h 37m
2 stops
BOS4:37 pmBoston Logan Intl
$640
Find similar
American Airlines
Dec 23
BOS2:04 pmBoston Logan Intl
10h 31m
2 stops
YWG11:35 pmWinnipeg
Dec 30
YWG6:00 amWinnipeg
13h 26m
2 stops
BOS8:26 pmBoston Logan Intl
$715
Find similar
American Airlines
Dec 23
BOS6:00 amBoston Logan Intl
18h 35m
3 stops
YWG11:35 pmWinnipeg
Dec 30
YWG6:00 amWinnipeg
9h 37m
2 stops
BOS4:37 pmBoston Logan Intl
$747
Find similar

Air Canada flights from Massachusetts to Winnipeg

Our best Air Canada deals on Massachusetts to Winnipeg flight tickets
Air Canada
Jan 16
BOS5:30 amBoston Logan Intl
5h 46m
1 stop
YWG10:16 amWinnipeg
Jan 19
YWG5:30 amWinnipeg
5h 42m
1 stop
BOS12:12 pmBoston Logan Intl
$387
Find similar
Air Canada
Feb 24
BOS10:15 amBoston Logan Intl
7h 20m
1 stop
YWG4:35 pmWinnipeg
Feb 26
YWG8:15 amWinnipeg
5h 37m
1 stop
BOS2:52 pmBoston Logan Intl
$552
Find similar
Air Canada
Feb 24
BOS5:30 amBoston Logan Intl
5h 46m
1 stop
YWG10:16 amWinnipeg
Feb 26
YWG8:15 amWinnipeg
5h 37m
1 stop
BOS2:52 pmBoston Logan Intl
$553
Find similar

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 832,500 searches. Data last updated November 6, 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

Thu 2/5

9:00 am-7:09 pm

1 stop11h 09m

Winnipeg

Fri 2/6

7:30 am-1:04 am

1 stop16h 34m

$373

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 1/16

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

Mon 1/19

5:30 am-12:12 pm

1 stop5h 42m

$387

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 2/5

7:00 am-11:32 am

2 stops29h 32m

Winnipeg

Fri 2/6

8:20 pm-11:05 am

1 stop13h 45m

$416

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 2/5

7:00 am-11:32 am

2 stops29h 32m

Winnipeg

Fri 2/6

8:20 pm-11:15 pm

2 stops25h 55m

$441

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 2/5

3:43 pm-11:32 am

2 stops20h 49m

Winnipeg

Fri 2/6

2:40 pm-11:15 pm

3 stops31h 35m

$451

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 2/24

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

Thu 2/26

8:15 am-2:52 pm

1 stop5h 37m

$552

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 12/23

6:00 am-11:35 pm

2 stops18h 35m

Winnipeg

Tue 12/30

6:00 am-4:37 pm

2 stops9h 37m

$640

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 12/22

6:01 am-11:57 am

1 stop6h 56m

Winnipeg

Tue 12/30

2:20 pm-12:45 am

1 stop9h 25m

$650

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 12/23

1:25 pm-11:35 pm

1 stop11h 10m

Winnipeg

Mon 12/29

6:00 am-10:05 pm

1 stop15h 05m

$673

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 12/23

2:04 pm-11:35 pm

2 stops10h 31m

Winnipeg

Tue 12/30

6:00 am-8:26 pm

2 stops13h 26m

$715

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?

In general, July is the cheapest month to fly from Massachusetts to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $233. If you’re not able to fly to Winnipeg in July, then January is your next best option. Flight prices from Massachusetts to Winnipeg during January average around $341.

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

The cheapest day to depart on your flight to Winnipeg is on a Sunday when prices can be found for as low as $354. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $789.

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

The cheapest time of day to fly to Winnipeg is at noon when flights can be purchased for as low as $405. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $552 on average. Flights to Winnipeg from Massachusetts in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

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 $434 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 $291 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.
Search flight deals

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

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

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Massachusetts to Winnipeg Airport.

  • What documentation or ID do you need to fly to Winnipeg Airport?

    The required travel and health documents for your Winnipeg Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Winnipeg Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Massachusetts to Winnipeg

Compare and see reviews for airlines that fly from Massachusetts to Winnipeg with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $134Free CancellationRating
7.1
10,405 reviews
Search Air Canada flights
United AirlinesPriceFrom $172Free CancellationRating
7.4
9,001 reviews
Search United Airlines flights
DeltaPriceFrom $228Free CancellationRating
7.9
8,004 reviews
Search Delta flights
Porter AirlinesPriceFrom $335Free CancellationRating
8.0
387 reviews
Search Porter Airlines flights

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Scanterbury
Selkirk
Morden

Why use momondo?

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

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 Massachusetts to Winnipeg for you.

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

Yes. All flights to Winnipeg from Massachusetts on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Massachusetts to Winnipeg.

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

Yes. momondo can track prices for Massachusetts to Winnipeg flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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