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

Porter Airlines is the most popular carrier 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 1 as of June 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.

$176 Cheap Flights from Winnipeg to Massachusetts in 2026

Discover deals from 900+ travel sites with momondo.

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.

12:15 pm - 6:35 pm

YWG

BOS

5h 20m

1 stop

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

$292Porter Airlines

Fri, Jul 10 - Thu, Jul 16

8:10 am - 2:41 pm

YWG

BOS

5h 31m

1 stop

3:35 pm - 9:14 pm

BOS

YWG

6h 39m

1 stop

$308Air Canada

Mon, Sep 14 - Fri, Sep 18

8:15 am - 4:03 pm

YWG

BOS

6h 48m

1 stop

5:45 am - 2:25 pm

BOS

YWG

9h 40m

2 stops

$314Air Canada

Fri, Jul 10 - Thu, Jul 16

5:00 am - 2:41 pm

YWG

BOS

8h 41m

2 stops

5:45 am - 2:25 pm

BOS

YWG

9h 40m

2 stops

$316Air Canada

Fri, Jul 10 - Thu, Jul 16

3:20 pm - 10:38 pm

YWG

BOS

6h 18m

1 stop

6:00 am - 11:15 am

BOS

YWG

6h 15m

1 stop

$322Air Canada

Fri, Aug 7 - Sat, Aug 15

3:20 pm - 10:38 pm

YWG

BOS

6h 18m

1 stop

6:00 am - 11:15 am

BOS

YWG

6h 15m

1 stop

$327Air Canada

Mon, Jul 13 - Tue, Jul 21

3:58 pm - 11:59 pm

YWG

BOS

7h 01m

1 stop

5:55 am - 11:56 am

BOS

YWG

7h 01m

1 stop

$329Delta

Mon, Sep 14 - Fri, Sep 18

7:00 am - 9:36 pm

YWG

ALB

13h 36m

1 stop

6:00 am - 10:33 pm

ALB

YWG

17h 33m

2 stops

$505United Airlines

Tue, Aug 11 - Tue, Aug 18

7:00 am - 9:27 pm

YWG

ALB

13h 27m

1 stop

8:10 am - 10:33 pm

ALB

YWG

15h 23m

1 stop

$536United Airlines

Sat, Jul 11 - Fri, Sep 4

7:00 am - 9:27 pm

YWG

ALB

13h 27m

1 stop

8:10 am - 10:33 pm

ALB

YWG

15h 23m

1 stop

$537United Airlines

Sat, Jul 11 - Fri, Sep 4

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United Airlines flights from Winnipeg to Massachusetts

Our best United Airlines deals on Winnipeg to Massachusetts flight tickets

United Airlines

Jul 13

YWG12:56 pmWinnipeg

11h 18m

1 stop

BOS1:14 amBoston Logan Intl

Jul 14

BOS6:05 pmBoston Logan Intl

18h 47m

2 stops

YWG11:52 amWinnipeg

$342

United Airlines

Sep 21

YWG2:00 pmWinnipeg

8h 30m

1 stop

BOS11:30 pmBoston Logan Intl

Sep 23

BOS3:13 pmBoston Logan Intl

8h 20m

1 stop

YWG10:33 pmWinnipeg

$345

United Airlines

Jul 14

YWG5:00 amWinnipeg

13h 30m

2 stops

BOS7:30 pmBoston Logan Intl

Jul 22

BOS6:00 amBoston Logan Intl

11h 20m

2 stops

YWG4:20 pmWinnipeg

$430

Porter Airlines flights from Winnipeg to Massachusetts

Our best Porter Airlines deals on Winnipeg to Massachusetts flight tickets

Porter Airlines

Jul 10

YWG12:15 pmWinnipeg

5h 20m

1 stop

BOS6:35 pmBoston Logan Intl

Jul 16

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

$292

Porter Airlines

Aug 7

YWG12:15 pmWinnipeg

5h 20m

1 stop

BOS6:35 pmBoston Logan Intl

Aug 13

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

$337

Porter Airlines

Aug 7

YWG12:15 pmWinnipeg

5h 35m

1 stop

BOS6:50 pmBoston Logan Intl

Aug 12

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

$350

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 7/10

12:15 pm-6:35 pm

1 stop5h 20m

Boston Logan Intl

Thu 7/16

10:05 am-3:19 pm

1 stop6h 14m

$292

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 9/14

8:10 am-2:41 pm

1 stop5h 31m

Boston Logan Intl

Fri 9/18

3:35 pm-9:14 pm

1 stop6h 39m

$308

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 7/10

8:15 am-4:03 pm

1 stop6h 48m

Boston Logan Intl

Thu 7/16

5:45 am-2:25 pm

2 stops9h 40m

$314

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 7/10

5:00 am-2:41 pm

2 stops8h 41m

Boston Logan Intl

Thu 7/16

5:45 am-2:25 pm

2 stops9h 40m

$316

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 8/7

3:20 pm-10:38 pm

1 stop6h 18m

Boston Logan Intl

Sat 8/15

6:00 am-11:15 am

1 stop6h 15m

$322

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 7/13

3:20 pm-10:38 pm

1 stop6h 18m

Boston Logan Intl

Tue 7/21

6:00 am-11:15 am

1 stop6h 15m

$327

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 9/14

3:58 pm-11:59 pm

1 stop7h 01m

Boston Logan Intl

Fri 9/18

5:55 am-11:56 am

1 stop7h 01m

$329

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 8/11

7:00 am-9:36 pm

1 stop13h 36m

Albany Intl

Tue 8/18

6:00 am-10:33 pm

2 stops17h 33m

$505

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 7/11

7:00 am-9:27 pm

1 stop13h 27m

Albany Intl

Fri 9/4

8:10 am-10:33 pm

1 stop15h 23m

$536

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 7/11

7:00 am-9:27 pm

1 stop13h 27m

Albany Intl

Fri 9/4

8:10 am-10:33 pm

1 stop15h 23m

$537

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, February 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 $116. If you aren’t able to travel to Massachusetts during the month of February, then flying in July is also cheap. Prices for this month can be found on momondo for an average of $127.

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 20m
Direct flights	None

The fastest flight from Winnipeg to Massachusetts takes 5h 20m

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 1 as of June 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 $215	Free Cancellation	Rating 7.1 11,270 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.