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

Porter Airlines and Delta 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 2 as of May 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.

$174 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.

11:40 am - 7:05 pm

YWG

BOS

6h 25m

1 stop

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

$276Porter Airlines

Wed, Jun 3 - Wed, Jun 10

8:00 am - 7:11 pm

YWG

BOS

10h 11m

1 stop

6:00 pm - 11:34 pm

BOS

YWG

6h 34m

1 stop

$279Delta

Sat, Oct 17 - Wed, Oct 21

11:40 am - 7:05 pm

YWG

BOS

6h 25m

1 stop

7:10 am - 5:58 pm

BOS

YWG

11h 48m

2 stops

$281Porter Airlines

Wed, Jun 3 - Wed, Jun 10

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

$292Porter Airlines

Tue, Jul 21 - Wed, Jul 29

11:40 am - 7:05 pm

YWG

BOS

6h 25m

1 stop

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

$293Porter Airlines

Wed, Jun 3 - Wed, Jun 10

12:20 pm - 9:27 pm

YWG

BOS

8h 07m

2 stops

10:50 am - 4:17 pm

BOS

YWG

6h 27m

1 stop

$294Air Canada

Sat, Oct 17 - Wed, Oct 21

6:00 am - 11:21 pm

YWG

ALB

16h 21m

2 stops

6:05 am - 12:55 am

ALB

YWG

19h 50m

2 stops

$390WestJet

Tue, Jul 7 - Tue, Jul 21

6:15 am - 11:21 pm

YWG

ALB

16h 06m

2 stops

6:00 am - 12:55 am

ALB

YWG

19h 55m

2 stops

$399WestJet

Sat, Jul 11 - Fri, Sep 4

6:15 am - 11:21 pm

YWG

ALB

16h 06m

2 stops

6:00 am - 12:55 am

ALB

YWG

19h 55m

2 stops

$400WestJet

Sat, Jul 11 - Fri, Sep 4

7:00 am - 9:27 pm

YWG

ALB

13h 27m

1 stop

12:20 pm - 10:38 pm

ALB

YWG

11h 18m

1 stop

$439Air Canada

Tue, Jul 7 - Tue, Jul 21

Porter Airlines flights from Winnipeg to Massachusetts

Our best Porter Airlines deals on Winnipeg to Massachusetts flight tickets

Porter Airlines

Jun 3

YWG11:40 amWinnipeg

6h 25m

1 stop

BOS7:05 pmBoston Logan Intl

Jun 10

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

$276

Porter Airlines

Jun 3

YWG11:40 amWinnipeg

6h 25m

1 stop

BOS7:05 pmBoston Logan Intl

Jun 10

BOS7:10 amBoston Logan Intl

11h 48m

2 stops

YWG5:58 pmWinnipeg

$281

Porter Airlines

Jul 21

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

Jul 29

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

$292

Delta flights from Winnipeg to Massachusetts

Our best Delta deals on Winnipeg to Massachusetts flight tickets

Delta

Oct 17

YWG8:00 amWinnipeg

10h 11m

1 stop

BOS7:11 pmBoston Logan Intl

Oct 21

BOS6:00 pmBoston Logan Intl

6h 34m

1 stop

YWG11:34 pmWinnipeg

$279

Delta

Oct 17

YWG6:35 amWinnipeg

9h 06m

1 stop

BOS4:41 pmBoston Logan Intl

Oct 21

BOS6:00 pmBoston Logan Intl

6h 34m

1 stop

YWG11:34 pmWinnipeg

$307

Delta

May 29

YWG6:40 amWinnipeg

9h 30m

1 stop

BOS5:10 pmBoston Logan Intl

Jun 3

BOS5:51 amBoston Logan Intl

6h 03m

1 stop

YWG10:54 amWinnipeg

$338

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 6/3

11:40 am-7:05 pm

1 stop6h 25m

Boston Logan Intl

Wed 6/10

10:05 am-3:19 pm

1 stop6h 14m

$276

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 10/17

8:00 am-7:11 pm

1 stop10h 11m

Boston Logan Intl

Wed 10/21

6:00 pm-11:34 pm

1 stop6h 34m

$279

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 6/3

11:40 am-7:05 pm

1 stop6h 25m

Boston Logan Intl

Wed 6/10

7:10 am-5:58 pm

2 stops11h 48m

$281

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 7/21

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Wed 7/29

10:05 am-3:19 pm

1 stop6h 14m

$292

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 6/3

11:40 am-7:05 pm

1 stop6h 25m

Boston Logan Intl

Wed 6/10

10:05 am-3:19 pm

1 stop6h 14m

$293

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 10/17

12:20 pm-9:27 pm

2 stops8h 07m

Boston Logan Intl

Wed 10/21

10:50 am-4:17 pm

1 stop6h 27m

$294

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 7/7

6:00 am-11:21 pm

2 stops16h 21m

Albany Intl

Tue 7/21

6:05 am-12:55 am

2 stops19h 50m

$390

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 7/11

6:15 am-11:21 pm

2 stops16h 06m

Albany Intl

Fri 9/4

6:00 am-12:55 am

2 stops19h 55m

$399

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 7/11

6:15 am-11:21 pm

2 stops16h 06m

Albany Intl

Fri 9/4

6:00 am-12:55 am

2 stops19h 55m

$400

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 7/7

7:00 am-9:27 pm

1 stop13h 27m

Albany Intl

Tue 7/21

12:20 pm-10:38 pm

1 stop11h 18m

$439

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, May 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 $100. If you aren’t able to travel to Massachusetts during the month of May, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $116.

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	6h 25m
Direct flights	None

The fastest flight from Winnipeg to Massachusetts takes 6h 25m

There are no direct flights from Winnipeg to Massachusetts. There are no popular flight routes from Winnipeg to Massachusetts.

Search flight deals

Frequently asked questions about flying 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 2 as of May 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
Air Canada	PriceFrom $127	Free Cancellation	Rating 7.1 11,017 reviews		Search Air Canada flights
United Airlines	PriceFrom $168	Free Cancellation	Rating 7.4 9,699 reviews		Search United Airlines 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.