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

WestJet, 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 August 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.

$155 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.

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

8h 15m1 stop Toronto Pearson Intl

10:05 am - 3:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 14m1 stop Toronto Pearson Intl

$251Porter Airlines

Wed, Sep 23 - Wed, Sep 30

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

8h 15m1 stop Toronto Pearson Intl

10:05 am - 3:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 14m1 stop Toronto Pearson Intl

$251Porter Airlines

Wed, Sep 23 - Tue, Sep 29

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

8h 15m1 stop Toronto Pearson Intl

10:05 am - 3:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 14m1 stop Toronto Pearson Intl

$259Porter Airlines

Wed, Sep 23 - Thu, Oct 1

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

8h 15m1 stop Toronto Pearson Intl

10:05 am - 3:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 14m1 stop Toronto Pearson Intl

$275Porter Airlines

Fri, Oct 2 - Mon, Oct 5

5:44 pm - 11:59 pmYWG Winnipeg-BOS Boston Logan Intl

5h 15m1 stop Minneapolis St Paul

5:55 am - 3:08 pmBOS Boston Logan Intl-YWG Winnipeg

10h 13m1 stop Minneapolis St Paul

$281Delta

Tue, Sep 22 - Fri, Oct 2

12:41 pm - 11:59 pmYWG Winnipeg-BOS Boston Logan Intl

10h 18m1 stop Minneapolis St Paul

5:55 am - 3:08 pmBOS Boston Logan Intl-YWG Winnipeg

10h 13m1 stop Minneapolis St Paul

$281Delta

Wed, Sep 23 - Fri, Oct 2

5:44 pm - 11:59 pmYWG Winnipeg-BOS Boston Logan Intl

5h 15m1 stop Minneapolis St Paul

7:05 am - 3:08 pmBOS Boston Logan Intl-YWG Winnipeg

9h 03m1 stop Minneapolis St Paul

$281Delta

Tue, Sep 22 - Thu, Oct 1

2:05 pm - 10:40 pmYWG Winnipeg-BOS Boston Logan Intl

7h 35m1 stop Toronto Pearson Intl

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

6h 12m1 stop Toronto Pearson Intl

$354Air Canada

Thu, Oct 1 - Sun, Oct 4

3:20 pm - 10:40 pmYWG Winnipeg-BOS Boston Logan Intl

6h 20m1 stop Toronto Pearson Intl

3:35 pm - 9:14 pmBOS Boston Logan Intl-YWG Winnipeg

6h 39m1 stop Montreal Pierre Elliott Trudeau Intl

$356Air Canada

Wed, Oct 7 - Wed, Oct 21

1:30 pm - 9:26 pmYWG Winnipeg-BOS Boston Logan Intl

6h 56m1 stop Montreal Pierre Elliott Trudeau Intl

5:30 am - 11:20 amBOS Boston Logan Intl-YWG Winnipeg

6h 50m1 stop Montreal Pierre Elliott Trudeau Intl

$361Air Canada

Fri, Oct 23 - Sun, Oct 25

Cheap last minute flights

Enter your travel dates to find the best prices.

12:46 pm - 11:58 pmYWG Winnipeg-BOS Boston Logan Intl

10h 12m1 stop Minneapolis St Paul

5:51 am - 3:08 pmBOS Boston Logan Intl-YWG Winnipeg

10h 17m1 stop Minneapolis St Paul

$669Delta

Mon, Aug 17 - Fri, Aug 21

12:15 pm - 6:50 pmYWG Winnipeg-BOS Boston Logan Intl

5h 35m1 stop Toronto Pearson Intl

7:10 am - 5:58 pmBOS Boston Logan Intl-YWG Winnipeg

11h 48m2 stops Toronto Island Ottawa

$684Porter Airlines

Mon, Aug 17 - Fri, Aug 21

7:45 pm - 9:53 amYWG Winnipeg-BOS Boston Logan Intl

13h 08m1 stop Toronto Pearson Intl

10:40 am - 3:14 pmBOS Boston Logan Intl-YWG Winnipeg

5h 34m1 stop Montreal Pierre Elliott Trudeau Intl

$758Air Canada

Mon, Aug 17 - Fri, Aug 21

3:58 pm - 10:01 pmYWG Winnipeg-BOS Boston Logan Intl

5h 03m1 stop Minneapolis St Paul

3:00 pm - 11:30 pmBOS Boston Logan Intl-YWG Winnipeg

9h 30m1 stop Minneapolis St Paul

$859Delta

Mon, Aug 17 - Fri, Aug 21

9:20 am - 8:55 pmYWG Winnipeg-BOS Boston Logan Intl

10h 35m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

7:10 am - 5:58 pmBOS Boston Logan Intl-YWG Winnipeg

11h 48m2 stops Toronto Island Ottawa

$866Porter Airlines

Mon, Aug 17 - Fri, Aug 21

12:15 pm - 6:50 pmYWG Winnipeg-BOS Boston Logan Intl

5h 35m1 stop Toronto Pearson Intl

7:10 am - 5:58 pmBOS Boston Logan Intl-YWG Winnipeg

11h 48m2 stops Toronto Island Ottawa

$872Porter Airlines

Mon, Aug 17 - Fri, Aug 21

12:46 pm - 11:58 pmYWG Winnipeg-BOS Boston Logan Intl

10h 12m1 stop Minneapolis St Paul

7:10 am - 4:52 pmBOS Boston Logan Intl-YWG Winnipeg

10h 42m1 stop Minneapolis St Paul

$876Delta

Mon, Aug 17 - Fri, Aug 21

9:20 am - 6:50 pmYWG Winnipeg-BOS Boston Logan Intl

8h 30m1 stop Toronto Pearson Intl

10:05 am - 3:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 14m1 stop Toronto Pearson Intl

$879Porter Airlines

Mon, Aug 17 - Fri, Aug 21

8:15 am - 4:03 pmYWG Winnipeg-BOS Boston Logan Intl

6h 48m1 stop Toronto Pearson Intl

3:40 pm - 9:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 39m1 stop Montreal Pierre Elliott Trudeau Intl

$983Air Canada

Sat, Aug 15 - Mon, Aug 17

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

22h 45m1 stop Toronto Pearson Intl

3:55 pm - 4:25 pmBOS Boston Logan Intl-YWG Winnipeg

25h 30m2 stops Ottawa Toronto Pearson Intl

$1,097Multiple Airlines

Sat, Aug 15 - Mon, Aug 17

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Porter Airlines flights from Winnipeg to Massachusetts

Our best Porter Airlines deals on Winnipeg to Massachusetts flight tickets

Porter Airlines

Sep 23

YWG9:20 amWinnipeg

8h 15m

1 stop

BOS6:35 pmBoston Logan Intl

Sep 30

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

$251

Porter Airlines

Sep 23

YWG9:20 amWinnipeg

8h 15m

1 stop

BOS6:35 pmBoston Logan Intl

Oct 1

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

$259

Porter Airlines

Oct 2

YWG9:20 amWinnipeg

8h 15m

1 stop

BOS6:35 pmBoston Logan Intl

Oct 5

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

$275

Delta flights from Winnipeg to Massachusetts

Our best Delta deals on Winnipeg to Massachusetts flight tickets

Delta

Sep 22

YWG5:44 pmWinnipeg

5h 15m

1 stop

BOS11:59 pmBoston Logan Intl

Oct 2

BOS5:55 amBoston Logan Intl

10h 13m

1 stop

YWG3:08 pmWinnipeg

$281

Delta

Sep 26

YWG6:40 amWinnipeg

9h 45m

1 stop

BOS5:25 pmBoston Logan Intl

Sep 29

BOS5:55 amBoston Logan Intl

6h 56m

1 stop

YWG11:51 amWinnipeg

$366

Delta

Aug 24

YWG5:42 pmWinnipeg

5h 16m

1 stop

BOS11:58 pmBoston Logan Intl

Aug 30

BOS8:15 amBoston Logan Intl

9h 37m

1 stop

YWG4:52 pmWinnipeg

$411

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 9/23

9:20 am-6:35 pm

1 stop8h 15m

Boston Logan Intl

Wed 9/30

10:05 am-3:19 pm

1 stop6h 14m

$251

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 9/23

9:20 am-6:35 pm

1 stop8h 15m

Boston Logan Intl

Tue 9/29

10:05 am-3:19 pm

1 stop6h 14m

$251

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 9/23

9:20 am-6:35 pm

1 stop8h 15m

Boston Logan Intl

Thu 10/1

10:05 am-3:19 pm

1 stop6h 14m

$259

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 10/2

9:20 am-6:35 pm

1 stop8h 15m

Boston Logan Intl

Mon 10/5

10:05 am-3:19 pm

1 stop6h 14m

$275

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 9/22

5:44 pm-11:59 pm

1 stop5h 15m

Boston Logan Intl

Fri 10/2

5:55 am-3:08 pm

1 stop10h 13m

$281

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 9/23

12:41 pm-11:59 pm

1 stop10h 18m

Boston Logan Intl

Fri 10/2

5:55 am-3:08 pm

1 stop10h 13m

$281

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 9/22

5:44 pm-11:59 pm

1 stop5h 15m

Boston Logan Intl

Thu 10/1

7:05 am-3:08 pm

1 stop9h 03m

$281

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 10/1

2:05 pm-10:40 pm

1 stop7h 35m

Boston Logan Intl

Sun 10/4

6:00 am-11:12 am

1 stop6h 12m

$354

Quickest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 10/7

3:20 pm-10:40 pm

1 stop6h 20m

Boston Logan Intl

Wed 10/21

3:35 pm-9:14 pm

1 stop6h 39m

$356

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 10/23

1:30 pm-9:26 pm

1 stop6h 56m

Boston Logan Intl

Sun 10/25

5:30 am-11:20 am

1 stop6h 50m

$361

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 June is also cheap. Prices for this month can be found on momondo for an average of $378.

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 2 as of August 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 11,470 reviews		Search Air Canada flights
Porter Airlines	PriceFrom $282	Free Cancellation	Rating 8.0 456 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.