What is the cheapest airline that flies from Winnipeg to Massachusetts?

Porter Airlines is the most popular carrier operating from Winnipeg to Massachusetts

What airlines fly to Massachusetts?

Air Canada, Delta and United Airlines are the top three most popular airlines that fly to Massachusetts from Winnipeg according to our data. Air Canada is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 3 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Winnipeg Airport to Massachusetts refresh daily.

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

The number of operators available for flights from Winnipeg Airport to Massachusetts is 3 as of December 2025.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, 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 required for your trip to Massachusetts 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 Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$157 Cheap Flights from Winnipeg to Massachusetts in 2025/26

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Find the cheapest flights from Winnipeg to Massachusetts

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:00 am - 11:57 pm

YWG

BOS

14h 57m1 stop

5:34 am - 6:03 pm

BOS

YWG

13h 29m1 stop

$263Multiple Airlines

lun., ene. 12 - lun., ene. 19

9:00 pm - 1:13 am

YWG

BOS

27h 13m2 stops

5:34 am - 6:03 pm

BOS

YWG

13h 29m1 stop

$266Multiple Airlines

lun., ene. 12 - lun., ene. 19

8:00 am - 11:57 pm

YWG

BOS

14h 57m1 stop

5:23 pm - 12:41 am

BOS

YWG

32h 18m3 stops

$314Multiple Airlines

lun., ene. 12 - lun., ene. 19

8:05 pm - 11:57 pm

YWG

BOS

26h 52m2 stops

5:27 pm - 6:03 pm

BOS

YWG

25h 36m1 stop

$315Multiple Airlines

dom., ene. 11 - dom., ene. 18

2:20 pm - 9:16 pm

YWG

ALB

5h 56m1 stop

7:30 pm - 11:57 am

ALB

YWG

17h 27m2 stops

$353United Airlines

lun., mar. 2 - mié., mar. 4

2:20 pm - 10:01 am

YWG

ALB

18h 41m2 stops

7:30 pm - 11:57 am

ALB

YWG

17h 27m2 stops

$354United Airlines

lun., mar. 2 - mié., mar. 4

6:00 am - 2:52 pm

YWG

BOS

7h 52m2 stops

5:30 am - 10:15 am

BOS

YWG

5h 45m1 stop

$423Air Canada

sáb., mar. 21 - lun., mar. 23

8:15 am - 2:52 pm

YWG

BOS

5h 37m1 stop

10:15 am - 4:35 pm

BOS

YWG

7h 20m1 stop

$428Air Canada

sáb., mar. 21 - lun., mar. 23

7:30 am - 1:24 pm

YWG

ALB

28h 54m1 stop

6:00 am - 3:07 pm

ALB

YWG

10h 07m1 stop

$466WestJet

vie., ene. 23 - dom., ene. 25

12:10 pm - 3:20 pm

YWG

ALB

26h 10m2 stops

7:23 am - 11:35 pm

ALB

YWG

17h 12m3 stops

$691American Airlines

vie., ene. 23 - dom., ene. 25

Air Canada flights from Winnipeg to Massachusetts

Our best Air Canada deals on Winnipeg to Massachusetts flight tickets

Air Canada

Mar 21

YWG6:00 amWinnipeg

7h 52m

2 stops

BOS2:52 pmBoston Logan Intl

Mar 23

BOS5:30 amBoston Logan Intl

5h 45m

1 stop

YWG10:15 amWinnipeg

$423

Find similar

Air Canada

Mar 21

YWG8:15 amWinnipeg

5h 37m

1 stop

BOS2:52 pmBoston Logan Intl

Mar 23

BOS10:15 amBoston Logan Intl

7h 20m

1 stop

YWG4:35 pmWinnipeg

$428

Find similar

Air Canada

Feb 2

YWG5:30 amWinnipeg

8h 22m

2 stops

BOS2:52 pmBoston Logan Intl

Feb 3

BOS10:15 amBoston Logan Intl

11h 13m

2 stops

YWG8:28 pmWinnipeg

$457

Find similar

United Airlines flights from Winnipeg to Massachusetts

Our best United Airlines deals on Winnipeg to Massachusetts flight tickets

United Airlines

Mar 2

YWG2:20 pmWinnipeg

5h 56m

1 stop

ALB9:16 pmAlbany Intl

Mar 4

ALB7:30 pmAlbany Intl

17h 27m

2 stops

YWG11:57 amWinnipeg

$353

Find similar

United Airlines

Mar 2

YWG2:20 pmWinnipeg

18h 41m

2 stops

ALB10:01 amAlbany Intl

Mar 4

ALB7:30 pmAlbany Intl

17h 27m

2 stops

YWG11:57 amWinnipeg

$354

Find similar

United Airlines

Jan 23

YWG5:30 amWinnipeg

14h 52m

2 stops

ALB9:22 pmAlbany Intl

Jan 25

ALB6:00 amAlbany Intl

6h 57m

1 stop

YWG11:57 amWinnipeg

$413

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

lun. 1/12

8:00 am-11:57 pm

1 stop14h 57m

Boston Logan Intl

lun. 1/19

5:34 am-6:03 pm

1 stop13h 29m

$263

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

lun. 1/12

9:00 pm-1:13 am

2 stops27h 13m

Boston Logan Intl

lun. 1/19

5:34 am-6:03 pm

1 stop13h 29m

$266

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

lun. 1/12

8:00 am-11:57 pm

1 stop14h 57m

Boston Logan Intl

lun. 1/19

5:23 pm-12:41 am

3 stops32h 18m

$314

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

dom. 1/11

8:05 pm-11:57 pm

2 stops26h 52m

Boston Logan Intl

dom. 1/18

5:27 pm-6:03 pm

1 stop25h 36m

$315

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

lun. 3/2

2:20 pm-9:16 pm

1 stop5h 56m

Albany Intl

mié. 3/4

7:30 pm-11:57 am

2 stops17h 27m

$353

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

lun. 3/2

2:20 pm-10:01 am

2 stops18h 41m

Albany Intl

mié. 3/4

7:30 pm-11:57 am

2 stops17h 27m

$354

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 3/21

6:00 am-2:52 pm

2 stops7h 52m

Boston Logan Intl

lun. 3/23

5:30 am-10:15 am

1 stop5h 45m

$423

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 3/21

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

lun. 3/23

10:15 am-4:35 pm

1 stop7h 20m

$428

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

vie. 1/23

7:30 am-1:24 pm

1 stop28h 54m

Albany Intl

dom. 1/25

6:00 am-3:07 pm

1 stop10h 07m

$466

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

vie. 1/23

12:10 pm-3:20 pm

2 stops26h 10m

Albany Intl

dom. 1/25

7:23 am-11:35 pm

3 stops17h 12m

$691

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

What is the cheapest month to fly to Massachusetts?

In general, June is the cheapest month to fly from Winnipeg to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $296. If you aren’t able to travel to Massachusetts during the month of June, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $320.

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

According to our data, Saturday is the cheapest day to fly to Massachusetts from Winnipeg. The lowest ticket price found for a Saturday departure recently was $369. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Winnipeg because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $618.

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

Our data shows that the cheapest Winnipeg to Massachusetts flights are usually those with departure times in the morning. Our users have found flights to Massachusetts in the morning for as low as $493. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $618 on average. Flights to Massachusetts from Winnipeg at noon 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 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 $420 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 $242 on momondo.

Cheap Winnipeg to Massachusetts flight deals and tips

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

Fastest flight time	5h 42m
Direct flights	None

The fastest flight from Winnipeg to Massachusetts takes 5h 42m

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 refresh daily.
How many operators does momondo search for flights from Winnipeg Airport to Massachusetts?
The number of operators available for flights from Winnipeg Airport to Massachusetts is 3 as of December 2025.
How old do you have to be to fly from Winnipeg Airport to Massachusetts?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, 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 required for your trip to Massachusetts 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 Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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 Airlines	PriceFrom $100	Free Cancellation	Rating 7.4 9,092 reviews	Search United Airlines flights
Air Canada	PriceFrom $212	Free Cancellation	Rating 7.1 10,526 reviews	Search Air Canada flights
Delta	PriceFrom $241	Free Cancellation	Rating 7.9 8,008 reviews	Search Delta 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?

momondo does allow users to show only those flights to Massachusetts from Winnipeg which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Winnipeg and Massachusetts by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Massachusetts, momondo offers a useful price alert feature which will track prices for flights to Massachusetts from Winnipeg and alert you when they change.