What airlines fly to Massachusetts?

Air Canada, United Airlines and Delta 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 39% 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.

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

United Airlines, Delta, and WestJet are the most popular carriers operating from Winnipeg to Massachusetts

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 March 2026.

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.

$182 Cheap Flights from Winnipeg to Massachusetts in 2026

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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.

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

$287Porter Airlines

Tue, May 19 - Tue, May 26

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

$301Porter Airlines

Tue, May 19 - Tue, Jun 2

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

7:10 am - 5:58 pm

BOS

YWG

11h 48m

2 stops

$302Porter Airlines

Tue, May 19 - Tue, May 26

5:10 am - 11:46 am

YWG

BOS

5h 36m

1 stop

5:10 am - 11:08 am

BOS

YWG

6h 58m

1 stop

$315Air Canada

Sun, May 10 - Sat, May 23

5:10 am - 2:47 pm

YWG

BOS

8h 37m

2 stops

5:10 am - 11:08 am

BOS

YWG

6h 58m

1 stop

$323Air Canada

Fri, May 1 - Tue, May 5

5:20 pm - 11:35 pm

YWG

BOS

5h 15m

1 stop

5:51 am - 10:54 am

BOS

YWG

6h 03m

1 stop

$329Delta

Fri, May 1 - Thu, May 7

2:00 pm - 12:53 am

YWG

ALB

9h 53m

1 stop

6:05 am - 11:52 am

ALB

YWG

6h 47m

1 stop

$330United Airlines

Mon, Apr 20 - Fri, Apr 24

8:45 am - 10:13 am

YWG

ALB

24h 28m

2 stops

7:33 pm - 11:52 am

ALB

YWG

17h 19m

2 stops

$331United Airlines

Sat, Apr 18 - Wed, Apr 22

6:15 am - 11:06 pm

YWG

ALB

15h 51m

2 stops

6:00 am - 12:55 am

ALB

YWG

19h 55m

2 stops

$410WestJet

Sat, Jul 11 - Fri, Sep 4

6:15 am - 11:06 pm

YWG

ALB

15h 51m

2 stops

6:00 am - 12:55 am

ALB

YWG

19h 55m

2 stops

$411WestJet

Sat, Jul 11 - Fri, Sep 4

Delta flights from Winnipeg to Massachusetts

Our best Delta deals on Winnipeg to Massachusetts flight tickets

Delta

May 1

YWG5:20 pmWinnipeg

5h 15m

1 stop

BOS11:35 pmBoston Logan Intl

May 7

BOS5:51 amBoston Logan Intl

6h 03m

1 stop

YWG10:54 amWinnipeg

$329

Delta

Jun 18

YWG4:09 pmWinnipeg

6h 43m

1 stop

BOS11:52 pmBoston Logan Intl

Jun 21

BOS7:10 amBoston Logan Intl

9h 13m

1 stop

YWG3:23 pmWinnipeg

$332

Delta

May 1

YWG5:20 pmWinnipeg

5h 15m

1 stop

BOS11:35 pmBoston Logan Intl

May 8

BOS5:51 amBoston Logan Intl

6h 03m

1 stop

YWG10:54 amWinnipeg

$351

Air Canada flights from Winnipeg to Massachusetts

Our best Air Canada deals on Winnipeg to Massachusetts flight tickets

Air Canada

May 10

YWG5:10 amWinnipeg

5h 36m

1 stop

BOS11:46 amBoston Logan Intl

May 23

BOS5:10 amBoston Logan Intl

6h 58m

1 stop

YWG11:08 amWinnipeg

$315

Air Canada

May 1

YWG5:10 amWinnipeg

8h 37m

2 stops

BOS2:47 pmBoston Logan Intl

May 5

BOS5:10 amBoston Logan Intl

6h 58m

1 stop

YWG11:08 amWinnipeg

$323

Air Canada

May 10

YWG5:10 amWinnipeg

5h 36m

1 stop

BOS11:46 amBoston Logan Intl

May 23

BOS5:10 amBoston Logan Intl

6h 58m

1 stop

YWG11:08 amWinnipeg

$327

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 5/19

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Tue 5/26

10:05 am-3:19 pm

1 stop6h 14m

$287

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 5/19

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Tue 6/2

10:05 am-3:19 pm

1 stop6h 14m

$301

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 5/19

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Tue 5/26

7:10 am-5:58 pm

2 stops11h 48m

$302

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 5/10

5:10 am-11:46 am

1 stop5h 36m

Boston Logan Intl

Sat 5/23

5:10 am-11:08 am

1 stop6h 58m

$315

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 5/1

5:10 am-2:47 pm

2 stops8h 37m

Boston Logan Intl

Tue 5/5

5:10 am-11:08 am

1 stop6h 58m

$323

Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 5/1

5:20 pm-11:35 pm

1 stop5h 15m

Boston Logan Intl

Thu 5/7

5:51 am-10:54 am

1 stop6h 03m

$329

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Mon 4/20

2:00 pm-12:53 am

1 stop9h 53m

Albany Intl

Fri 4/24

6:05 am-11:52 am

1 stop6h 47m

$330

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 4/18

8:45 am-10:13 am

2 stops24h 28m

Albany Intl

Wed 4/22

7:33 pm-11:52 am

2 stops17h 19m

$331

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 7/11

6:15 am-11:06 pm

2 stops15h 51m

Albany Intl

Fri 9/4

6:00 am-12:55 am

2 stops19h 55m

$410

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 7/11

6:15 am-11:06 pm

2 stops15h 51m

Albany Intl

Fri 9/4

6:00 am-12:55 am

2 stops19h 55m

$411

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 $300. 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 $332.

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 $471 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 $246 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 15m
Direct flights	None

The fastest flight from Winnipeg to Massachusetts takes 5h 15m

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 March 2026.
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 9,428 reviews	Search United Airlines flights
Delta	PriceFrom $182	Free Cancellation	Rating 7.9 8,292 reviews	Search Delta flights
Air Canada	PriceFrom $212	Free Cancellation	Rating 7.1 10,801 reviews	Search Air Canada 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.