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

Delta 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 2 as of September 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.

$163 Cheap Flights from Winnipeg to Massachusetts in 2026/27

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.

2:00 pm - 11:24 pmYWG Winnipeg-BOS Boston Logan Intl

8h 24m1 stop Chicago O'Hare Intl

6:00 am - 12:37 pmBOS Boston Logan Intl-YWG Winnipeg

7h 37m1 stop Chicago O'Hare Intl

$277United Airlines

Wed, Oct 21 - Thu, Oct 22

5:00 am - 11:50 amYWG Winnipeg-BOS Boston Logan Intl

5h 50m1 stop Toronto Pearson Intl

6:00 am - 11:12 amBOS Boston Logan Intl-YWG Winnipeg

6h 12m1 stop Toronto Pearson Intl

$288Air Canada

Wed, Oct 21 - Thu, Oct 22

11:40 am - 9:32 pmYWG Winnipeg-BOS Boston Logan Intl

8h 52m2 stops Ottawa Toronto Island

1:15 pm - 6:10 pmBOS Boston Logan Intl-YWG Winnipeg

5h 55m1 stop Ottawa

$291Porter Airlines

Thu, Oct 29 - Thu, Nov 5

11:40 am - 9:32 pmYWG Winnipeg-BOS Boston Logan Intl

8h 52m2 stops Ottawa Toronto Island

8:00 am - 6:10 pmBOS Boston Logan Intl-YWG Winnipeg

11h 10m2 stops Toronto Island Ottawa

$292Porter Airlines

Thu, Oct 29 - Thu, Nov 5

11:40 am - 9:32 pmYWG Winnipeg-BOS Boston Logan Intl

8h 52m2 stops Ottawa Toronto Island

8:00 am - 6:10 pmBOS Boston Logan Intl-YWG Winnipeg

11h 10m2 stops Toronto Island Ottawa

$294Porter Airlines

Tue, Nov 24 - Sun, Nov 29

7:10 pm - 9:55 amYWG Winnipeg-BOS Boston Logan Intl

13h 45m1 stop Toronto Pearson Intl

5:05 pm - 11:47 pmBOS Boston Logan Intl-YWG Winnipeg

7h 42m1 stop Toronto Pearson Intl

$299Air Canada

Fri, Oct 16 - Tue, Oct 20

6:35 am - 4:44 pmYWG Winnipeg-BOS Boston Logan Intl

9h 09m1 stop Minneapolis St Paul

2:59 pm - 11:33 pmBOS Boston Logan Intl-YWG Winnipeg

9h 34m1 stop Minneapolis St Paul

$308Delta

Wed, Nov 25 - Mon, Nov 30

5:32 pm - 11:44 pmYWG Winnipeg-BOS Boston Logan Intl

5h 12m1 stop Minneapolis St Paul

2:59 pm - 11:33 pmBOS Boston Logan Intl-YWG Winnipeg

9h 34m1 stop Minneapolis St Paul

$317Delta

Wed, Nov 25 - Mon, Nov 30

6:35 am - 4:44 pmYWG Winnipeg-BOS Boston Logan Intl

9h 09m1 stop Minneapolis St Paul

2:59 pm - 11:33 pmBOS Boston Logan Intl-YWG Winnipeg

9h 34m1 stop Minneapolis St Paul

$317Delta

Wed, Nov 25 - Mon, Nov 30

2:05 pm - 9:28 pmYWG Winnipeg-BOS Boston Logan Intl

6h 23m1 stop Montreal Pierre Elliott Trudeau Intl

10:25 am - 4:38 pmBOS Boston Logan Intl-YWG Winnipeg

7h 13m1 stop Montreal Pierre Elliott Trudeau Intl

$582Air Canada

Wed, Nov 25 - Mon, Nov 30

Cheap last minute flights

Enter your travel dates to find the best prices.

9:20 am - 6:35 pmYWG Winnipeg-BOS Boston Logan Intl

8h 15m1 stop Toronto Pearson Intl

10:05 am - 3:20 pmBOS Boston Logan Intl-YWG Winnipeg

6h 15m1 stop Toronto Pearson Intl

$630Porter Airlines

Fri, Oct 2 - Mon, Oct 5

5:10 pm - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

14h 55m1 stop Toronto Pearson Intl

7:30 pm - 4:25 pmBOS Boston Logan Intl-YWG Winnipeg

21h 55m1 stop Toronto Pearson Intl

$701Multiple Airlines

Sun, Oct 4 - Mon, Oct 5

5:10 pm - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

14h 55m1 stop Toronto Pearson Intl

3:55 pm - 3:25 pmBOS Boston Logan Intl-YWG Winnipeg

24h 30m2 stops Ottawa Calgary

$766Multiple Airlines

Sun, Oct 4 - Mon, Oct 5

9:20 am - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

22h 45m1 stop Toronto Pearson Intl

7:00 am - 5:58 pmBOS Boston Logan Intl-YWG Winnipeg

11h 58m2 stops Toronto Island Ottawa

$823Porter Airlines

Fri, Oct 2 - Mon, Oct 5

4:15 pm - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

15h 50m2 stops Ottawa Toronto Pearson Intl

7:00 am - 5:58 pmBOS Boston Logan Intl-YWG Winnipeg

11h 58m2 stops Toronto Island Ottawa

$823Porter Airlines

Fri, Oct 2 - Mon, Oct 5

9:20 am - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

22h 45m1 stop Toronto Pearson Intl

7:30 pm - 3:20 pmBOS Boston Logan Intl-YWG Winnipeg

20h 50m1 stop Toronto Pearson Intl

$860Porter Airlines

Fri, Oct 2 - Mon, Oct 5

9:20 am - 10:40 pmYWG Winnipeg-BOS Boston Logan Intl

12h 20m2 stops Toronto Pearson Intl New York LaGuardia

3:55 pm - 3:20 pmBOS Boston Logan Intl-YWG Winnipeg

24h 25m2 stops Ottawa Toronto Pearson Intl

$867Porter Airlines

Sun, Oct 4 - Mon, Oct 5

11:40 am - 3:14 pmYWG Winnipeg-BOS Boston Logan Intl

26h 34m2 stops Ottawa Toronto Island

7:00 am - 5:58 pmBOS Boston Logan Intl-YWG Winnipeg

11h 58m2 stops Toronto Island Ottawa

$902Porter Airlines

Fri, Oct 2 - Mon, Oct 5

8:45 pm - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

11h 20m1 stop Toronto Pearson Intl

7:00 am - 5:58 pmBOS Boston Logan Intl-YWG Winnipeg

11h 58m2 stops Toronto Island Ottawa

$904Porter Airlines

Fri, Oct 2 - Mon, Oct 5

8:45 pm - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

11h 20m1 stop Toronto Pearson Intl

10:05 am - 3:20 pmBOS Boston Logan Intl-YWG Winnipeg

6h 15m1 stop Toronto Pearson Intl

$912Porter Airlines

Fri, Oct 2 - Mon, Oct 5

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Air Canada flights from Winnipeg to Massachusetts

Our best Air Canada deals on Winnipeg to Massachusetts flight tickets

Air Canada

Oct 21

YWG5:00 amWinnipeg

5h 50m

1 stop

BOS11:50 amBoston Logan Intl

Oct 22

BOS6:00 amBoston Logan Intl

6h 12m

1 stop

YWG11:12 amWinnipeg

$288

Air Canada

Oct 16

YWG7:10 pmWinnipeg

13h 45m

1 stop

BOS9:55 amBoston Logan Intl

Oct 20

BOS5:05 pmBoston Logan Intl

7h 42m

1 stop

YWG11:47 pmWinnipeg

$299

Porter Airlines flights from Winnipeg to Massachusetts

Our best Porter Airlines deals on Winnipeg to Massachusetts flight tickets

Porter Airlines

Oct 29

YWG11:40 amWinnipeg

8h 52m

2 stops

BOS9:32 pmBoston Logan Intl

Nov 5

BOS1:15 pmBoston Logan Intl

5h 55m

1 stop

YWG6:10 pmWinnipeg

$291

Porter Airlines

Oct 29

YWG11:40 amWinnipeg

8h 52m

2 stops

BOS9:32 pmBoston Logan Intl

Nov 5

BOS8:00 amBoston Logan Intl

11h 10m

2 stops

YWG6:10 pmWinnipeg

$292

Porter Airlines

Nov 24

YWG11:40 amWinnipeg

8h 52m

2 stops

BOS9:32 pmBoston Logan Intl

Nov 29

BOS8:00 amBoston Logan Intl

11h 10m

2 stops

YWG6:10 pmWinnipeg

$294

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 10/21

2:00 pm-11:24 pm

1 stop8h 24m

Boston Logan Intl

Thu 10/22

6:00 am-12:37 pm

1 stop7h 37m

$277

Quickest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 10/21

5:00 am-11:50 am

1 stop5h 50m

Boston Logan Intl

Thu 10/22

6:00 am-11:12 am

1 stop6h 12m

$288

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 10/29

11:40 am-9:32 pm

2 stops8h 52m

Boston Logan Intl

Thu 11/5

1:15 pm-6:10 pm

1 stop5h 55m

$291

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 10/29

11:40 am-9:32 pm

2 stops8h 52m

Boston Logan Intl

Thu 11/5

8:00 am-6:10 pm

2 stops11h 10m

$292

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 11/24

11:40 am-9:32 pm

2 stops8h 52m

Boston Logan Intl

Sun 11/29

8:00 am-6:10 pm

2 stops11h 10m

$294

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 10/16

7:10 pm-9:55 am

1 stop13h 45m

Boston Logan Intl

Tue 10/20

5:05 pm-11:47 pm

1 stop7h 42m

$299

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 11/25

6:35 am-4:44 pm

1 stop9h 09m

Boston Logan Intl

Mon 11/30

2:59 pm-11:33 pm

1 stop9h 34m

$308

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 11/25

5:32 pm-11:44 pm

1 stop5h 12m

Boston Logan Intl

Mon 11/30

2:59 pm-11:33 pm

1 stop9h 34m

$317

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 11/25

6:35 am-4:44 pm

1 stop9h 09m

Boston Logan Intl

Mon 11/30

2:59 pm-11:33 pm

1 stop9h 34m

$317

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 11/25

2:05 pm-9:28 pm

1 stop6h 23m

Boston Logan Intl

Mon 11/30

10:25 am-4:38 pm

1 stop7h 13m

$582

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, August 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 $348. If you aren’t able to travel to Massachusetts during the month of August, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $357.

Cheap Winnipeg to Massachusetts flight deals and tips

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

Best Price Found	$163
Fastest flight time	8h 35m
Direct flights	None

The best one-way flight to Massachusetts from Winnipeg in the past 72 hours is $163. The best round-trip flight deal from Winnipeg to Massachusetts found on momondo in the last 72 hours is $277.

The fastest flight from Winnipeg to Massachusetts takes 8h 35m

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 September 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 11,706 reviews		Search Air Canada flights
Porter Airlines	PriceFrom $282	Free Cancellation	Rating 8.0 465 reviews		Search Porter 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.