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Cheap flights from Massachusetts to Winnipeg from $221

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 1/6. 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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Find the cheapest flights from Massachusetts to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
12:10 pm - 7:12 pm
BOS
-
YWG
32h 02m2 stops
Multiple Airlines Logo
8:00 am - 11:57 pm
YWG
-
BOS
14h 57m1 stop
$274Multiple Airlines
Mon, Jan 19 - Mon, Jan 26
Multiple Airlines Logo
5:23 pm - 3:09 pm
BOS
-
YWG
22h 46m2 stops
Multiple Airlines Logo
5:00 am - 11:57 pm
YWG
-
BOS
17h 57m2 stops
$301Multiple Airlines
Tue, Feb 3 - Tue, Feb 10
Multiple Airlines Logo
5:23 pm - 3:09 pm
BOS
-
YWG
22h 46m2 stops
Multiple Airlines Logo
5:00 am - 2:38 pm
YWG
-
BOS
32h 38m3 stops
$311Multiple Airlines
Tue, Feb 3 - Tue, Feb 10
Multiple Airlines Logo
5:34 am - 6:05 pm
BOS
-
YWG
37h 31m3 stops
Multiple Airlines Logo
5:00 am - 2:38 pm
YWG
-
BOS
32h 38m3 stops
$336Multiple Airlines
Tue, Feb 3 - Tue, Feb 10
Multiple Airlines Logo
6:00 am - 12:40 am
BOS
-
YWG
19h 40m2 stops
Multiple Airlines Logo
4:25 pm - 6:10 pm
YWG
-
BOS
24h 45m1 stop
$369Multiple Airlines
Tue, Feb 3 - Tue, Feb 10
Multiple Airlines Logo
3:30 pm - 11:13 am
BOS
-
YWG
20h 43m1 stop
Multiple Airlines Logo
8:00 am - 11:57 pm
YWG
-
BOS
14h 57m1 stop
$395Multiple Airlines
Mon, Jan 19 - Mon, Jan 26
Multiple Airlines Logo
3:30 pm - 12:39 am
BOS
-
YWG
10h 09m2 stops
Multiple Airlines Logo
7:30 am - 1:13 am
YWG
-
BOS
16h 43m1 stop
$473Multiple Airlines
Mon, Feb 16 - Wed, Feb 18
Air Canada Logo
10:15 am - 4:35 pm
BOS
-
YWG
7h 20m1 stop
Air Canada Logo
8:15 am - 2:52 pm
YWG
-
BOS
5h 37m1 stop
$495Air Canada
Mon, Mar 2 - Wed, Mar 4
Air Canada Logo
10:15 am - 4:35 pm
BOS
-
YWG
7h 20m1 stop
Air Canada Logo
6:00 am - 2:52 pm
YWG
-
BOS
7h 52m2 stops
$500Air Canada
Mon, Mar 2 - Wed, Mar 4
Air Canada Logo
10:15 am - 8:28 pm
BOS
-
YWG
11h 13m2 stops
Air Canada Logo
6:00 am - 2:52 pm
YWG
-
BOS
7h 52m2 stops
$506Air Canada
Mon, Mar 2 - Wed, Mar 4

Air Canada flights from Massachusetts to Winnipeg

Our best Air Canada deals on Massachusetts to Winnipeg flight tickets
Air Canada
Feb 3
BOS10:15 amBoston Logan Intl
7h 20m
1 stop
YWG4:35 pmWinnipeg
Feb 7
YWG8:15 amWinnipeg
5h 37m
1 stop
BOS2:52 pmBoston Logan Intl
$388
Find similar
Air Canada
Mar 2
BOS10:15 amBoston Logan Intl
7h 20m
1 stop
YWG4:35 pmWinnipeg
Mar 4
YWG8:15 amWinnipeg
5h 37m
1 stop
BOS2:52 pmBoston Logan Intl
$495
Find similar
Air Canada
Mar 2
BOS10:15 amBoston Logan Intl
7h 20m
1 stop
YWG4:35 pmWinnipeg
Mar 4
YWG6:00 amWinnipeg
7h 52m
2 stops
BOS2:52 pmBoston Logan Intl
$500
Find similar

Delta flights from Massachusetts to Winnipeg

Our best Delta deals on Massachusetts to Winnipeg flight tickets
Delta
Jun 14
BOS7:10 amBoston Logan Intl
10h 44m
1 stop
YWG4:54 pmWinnipeg
Jun 20
YWG5:38 pmWinnipeg
5h 14m
1 stop
BOS11:52 pmBoston Logan Intl
$579
Find similar
Delta
Jun 14
BOS7:10 amBoston Logan Intl
10h 44m
1 stop
YWG4:54 pmWinnipeg
Jun 20
YWG12:40 pmWinnipeg
8h 40m
1 stop
BOS10:20 pmBoston Logan Intl
$604
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 December 21, 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

Mon 1/19

12:10 pm-7:12 pm

2 stops32h 02m

Winnipeg

Mon 1/26

8:00 am-11:57 pm

1 stop14h 57m

$274

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 2/3

5:23 pm-3:09 pm

2 stops22h 46m

Winnipeg

Tue 2/10

5:00 am-11:57 pm

2 stops17h 57m

$301

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 2/3

5:23 pm-3:09 pm

2 stops22h 46m

Winnipeg

Tue 2/10

5:00 am-2:38 pm

3 stops32h 38m

$311

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 2/3

5:34 am-6:05 pm

3 stops37h 31m

Winnipeg

Tue 2/10

5:00 am-2:38 pm

3 stops32h 38m

$336

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 2/3

6:00 am-12:40 am

2 stops19h 40m

Winnipeg

Tue 2/10

4:25 pm-6:10 pm

1 stop24h 45m

$369

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 1/19

3:30 pm-11:13 am

1 stop20h 43m

Winnipeg

Mon 1/26

8:00 am-11:57 pm

1 stop14h 57m

$395

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 2/16

3:30 pm-12:39 am

2 stops10h 09m

Winnipeg

Wed 2/18

7:30 am-1:13 am

1 stop16h 43m

$473

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 3/2

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

Wed 3/4

8:15 am-2:52 pm

1 stop5h 37m

$495

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 3/2

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

Wed 3/4

6:00 am-2:52 pm

2 stops7h 52m

$500

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 3/2

10:15 am-8:28 pm

2 stops11h 13m

Winnipeg

Wed 3/4

6:00 am-2:52 pm

2 stops7h 52m

$506

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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2

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 August is your next best option. Flight prices from Massachusetts to Winnipeg during August average around $399.

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 $465 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 $303 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

Fastest flight time

6h 56m

Direct flights

None
The fastest flight from Massachusetts to Winnipeg takes 6h 56m
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
10,550 reviews
Search Air Canada flights
DeltaPriceFrom $143Free CancellationRating
7.9
8,017 reviews
Search Delta flights
United AirlinesPriceFrom $172Free CancellationRating
7.4
9,100 reviews
Search United Airlines flights

Traveling to a place near Winnipeg?

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

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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