What airlines fly to Winnipeg?

Air Canada, Porter Airlines and Delta are the top three most popular airlines that fly to Winnipeg from Boston according to our data. Air Canada is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Winnipeg. Keep in mind that there are 4 different airlines that fly to Winnipeg on a routine basis, so you have a few additional options to choose from.

Which airport is the most popular layover for flights between Boston and Winnipeg?

Toronto (YYZ) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest connection time from Boston to Winnipeg?

Montreal (YUL) has the shortest average layover time for this route: 1h 13m.

Which layover airport has the shortest travel time from Boston to Winnipeg?

Flights connecting via Montreal (YUL) have the shortest average one-way travel time: 5h 46m.

Which layover airport offers the lowest fares from Boston to Winnipeg?

Flights via Toronto (YYZ) offer the lowest average round-trip price of $366.

When did momondo last update prices for flights from Boston Logan Intl Airport to Winnipeg Airport?

Prices for flights from Boston Logan Intl Airport to Winnipeg Airport are updated daily.

How many operators does momondo search for flights from Boston Logan Intl Airport to Winnipeg Airport?

As of November 2026, there are 4 operators available to choose from for flights from Boston Logan Intl Airport to Winnipeg Airport.

How old do you have to be to fly from Boston Logan Intl Airport to Winnipeg Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Boston Logan Intl Airport to Winnipeg Airport.

What documentation or ID do you need to fly to Winnipeg Airport?

The travel and health documents required for your trip to Winnipeg Airport 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 Winnipeg Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$203 Cheap Flights from Boston to Winnipeg in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Boston to Winnipeg

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:30 pm - 10:15 amBOS Boston Logan Intl-YWG Winnipeg

16h 45m1 stop Toronto Pearson Intl

11:00 am - 7:10 pmYWG Winnipeg-BOS Boston Logan Intl

8h 10m1 stop Toronto Pearson Intl

$409Multiple Airlines

Sat, Dec 5 - Mon, Dec 14

4:35 pm - 10:15 amBOS Boston Logan Intl-YWG Winnipeg

17h 40m1 stop Toronto Island

11:00 am - 7:10 pmYWG Winnipeg-BOS Boston Logan Intl

8h 10m1 stop Toronto Pearson Intl

$413Multiple Airlines

Tue, Dec 8 - Sat, Dec 12

1:15 pm - 7:19 pmBOS Boston Logan Intl-YWG Winnipeg

6h 04m1 stop Ottawa

12:40 pm - 9:34 pmYWG Winnipeg-BOS Boston Logan Intl

8h 54m2 stops Ottawa Toronto Island

$445Porter Airlines

Mon, Mar 1 - Tue, Mar 9

8:00 am - 7:19 pmBOS Boston Logan Intl-YWG Winnipeg

11h 19m2 stops Toronto Island Ottawa

12:40 pm - 9:34 pmYWG Winnipeg-BOS Boston Logan Intl

8h 54m2 stops Ottawa Toronto Island

$455Porter Airlines

Mon, Mar 1 - Tue, Mar 9

5:30 am - 11:18 amBOS Boston Logan Intl-YWG Winnipeg

5h 48m1 stop Montreal Pierre Elliott Trudeau Intl

9:05 am - 2:53 pmYWG Winnipeg-BOS Boston Logan Intl

5h 48m1 stop Montreal Pierre Elliott Trudeau Intl

$698Air Canada

Tue, Dec 8 - Sat, Dec 12

5:30 am - 11:18 amBOS Boston Logan Intl-YWG Winnipeg

5h 48m1 stop Montreal Pierre Elliott Trudeau Intl

3:05 pm - 9:28 pmYWG Winnipeg-BOS Boston Logan Intl

6h 23m1 stop Montreal Pierre Elliott Trudeau Intl

$698Air Canada

Wed, Dec 23 - Wed, Dec 30

6:00 am - 11:39 amBOS Boston Logan Intl-YWG Winnipeg

6h 39m1 stop Chicago O'Hare Intl

2:15 pm - 9:33 pmYWG Winnipeg-BOS Boston Logan Intl

6h 18m1 stop Chicago O'Hare Intl

$933United Airlines

Sun, Apr 4 - Sun, Apr 4

6:00 am - 11:39 amBOS Boston Logan Intl-YWG Winnipeg

6h 39m1 stop Chicago O'Hare Intl

2:15 pm - 11:16 pmYWG Winnipeg-BOS Boston Logan Intl

8h 01m1 stop Chicago O'Hare Intl

$933United Airlines

Sat, Apr 3 - Sat, Apr 3

8:15 am - 12:44 amBOS Boston Logan Intl-YWG Winnipeg

16h 29m2 stops Cincinnati Cinci./N. Kentucky Minneapolis St Paul

6:25 am - 11:00 pmYWG Winnipeg-BOS Boston Logan Intl

16h 35m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

$1,153Delta

Sat, Dec 26 - Wed, Dec 30

5:30 am - 11:31 amBOS Boston Logan Intl-YWG Winnipeg

6h 01m1 stop Minneapolis St Paul

10:35 am - 11:59 pmYWG Winnipeg-BOS Boston Logan Intl

13h 24m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

$1,173Delta

Sat, Dec 26 - Mon, Dec 28

Cheap last minute flights

Enter your travel dates to find the best prices.

8:00 am - 1:44 amBOS Boston Logan Intl-YWG Winnipeg

17h 44m1 stop Toronto Island

9:35 pm - 11:44 amYWG Winnipeg-BOS Boston Logan Intl

14h 09m2 stops Calgary Atlanta Hartsfield-Jackson

$865Multiple Airlines

Fri, Nov 13 - Tue, Nov 17

8:00 am - 1:44 amBOS Boston Logan Intl-YWG Winnipeg

17h 44m1 stop Toronto Island

9:35 pm - 11:44 amYWG Winnipeg-BOS Boston Logan Intl

14h 09m2 stops Calgary Atlanta Hartsfield-Jackson

$872Multiple Airlines

Fri, Nov 13 - Tue, Nov 17

8:00 am - 1:44 amBOS Boston Logan Intl-YWG Winnipeg

17h 44m1 stop Toronto Island

9:35 pm - 11:44 amYWG Winnipeg-BOS Boston Logan Intl

14h 09m2 stops Calgary Atlanta Hartsfield-Jackson

$873Multiple Airlines

Fri, Nov 13 - Wed, Nov 18

8:00 am - 1:44 amBOS Boston Logan Intl-YWG Winnipeg

17h 44m1 stop Toronto Island

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

12h 05m1 stop Toronto Pearson Intl

$884Multiple Airlines

Fri, Nov 13 - Wed, Nov 18

8:00 am - 1:44 amBOS Boston Logan Intl-YWG Winnipeg

17h 44m1 stop Toronto Island

6:00 am - 7:10 pmYWG Winnipeg-BOS Boston Logan Intl

13h 10m1 stop Toronto Pearson Intl

$888Multiple Airlines

Fri, Nov 13 - Tue, Nov 17

8:00 am - 1:44 amBOS Boston Logan Intl-YWG Winnipeg

17h 44m1 stop Toronto Island

6:00 am - 7:10 pmYWG Winnipeg-BOS Boston Logan Intl

13h 10m1 stop Toronto Pearson Intl

$895Multiple Airlines

Fri, Nov 13 - Tue, Nov 17

5:30 am - 7:55 pmBOS Boston Logan Intl-YWG Winnipeg

14h 25m2 stops Detroit Metropolitan Wayne County Cancun

9:05 pm - 3:55 pmYWG Winnipeg-BOS Boston Logan Intl

18h 50m1 stop Toronto Pearson Intl

$955Multiple Airlines

Fri, Nov 13 - Wed, Nov 18

8:00 am - 7:06 pmBOS Boston Logan Intl-YWG Winnipeg

11h 06m2 stops Toronto Island Ottawa

12:35 pm - 9:35 pmYWG Winnipeg-BOS Boston Logan Intl

9h 00m2 stops Ottawa Toronto Island

$1,196Porter Airlines

Fri, Nov 13 - Tue, Nov 17

8:00 am - 7:06 pmBOS Boston Logan Intl-YWG Winnipeg

11h 06m2 stops Toronto Island Ottawa

12:35 pm - 12:35 pmYWG Winnipeg-BOS Boston Logan Intl

24h 00m2 stops Ottawa Toronto Island

$1,244Porter Airlines

Fri, Nov 13 - Wed, Nov 18

8:00 am - 7:06 pmBOS Boston Logan Intl-YWG Winnipeg

11h 06m2 stops Toronto Island Ottawa

12:35 pm - 3:55 pmYWG Winnipeg-BOS Boston Logan Intl

27h 20m2 stops Ottawa Toronto Island

$1,244Porter Airlines

Fri, Nov 13 - Tue, Nov 17

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Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets

Porter Airlines

Mar 1

BOS1:15 pmBoston Logan Intl

6h 04m

1 stop

YWG7:19 pmWinnipeg

Mar 9

YWG12:40 pmWinnipeg

8h 54m

2 stops

BOS9:34 pmBoston Logan Intl

$465

Porter Airlines

Mar 1

BOS1:15 pmBoston Logan Intl

6h 04m

1 stop

YWG7:19 pmWinnipeg

Mar 9

YWG12:40 pmWinnipeg

8h 54m

2 stops

BOS9:34 pmBoston Logan Intl

$469

Porter Airlines

Mar 1

BOS8:00 amBoston Logan Intl

11h 19m

2 stops

YWG7:19 pmWinnipeg

Mar 9

YWG12:40 pmWinnipeg

8h 54m

2 stops

BOS9:34 pmBoston Logan Intl

$477

American Airlines flights from Boston to Winnipeg

Our best American Airlines deals on Boston to Winnipeg flight tickets

American Airlines

Nov 20

BOS11:08 amBoston Logan Intl

11h 44m

2 stops

YWG10:52 pmWinnipeg

Nov 26

YWG7:00 amWinnipeg

26h 21m

3 stops

BOS9:21 amBoston Logan Intl

$1,150

American Airlines

Nov 25

BOS11:08 amBoston Logan Intl

11h 44m

2 stops

YWG10:52 pmWinnipeg

Nov 26

YWG7:00 amWinnipeg

26h 21m

3 stops

BOS9:21 amBoston Logan Intl

$1,429

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 12/5

5:30 pm-10:15 am

1 stop16h 45m

Winnipeg

Mon 12/14

11:00 am-7:10 pm

1 stop8h 10m

$409

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 12/8

4:35 pm-10:15 am

1 stop17h 40m

Winnipeg

Sat 12/12

11:00 am-7:10 pm

1 stop8h 10m

$413

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 3/1

1:15 pm-7:19 pm

1 stop6h 04m

Winnipeg

Tue 3/9

12:40 pm-9:34 pm

2 stops8h 54m

$445

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 3/1

8:00 am-7:19 pm

2 stops11h 19m

Winnipeg

Tue 3/9

12:40 pm-9:34 pm

2 stops8h 54m

$455

Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 12/8

5:30 am-11:18 am

1 stop5h 48m

Winnipeg

Sat 12/12

9:05 am-2:53 pm

1 stop5h 48m

$698

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 12/23

5:30 am-11:18 am

1 stop5h 48m

Winnipeg

Wed 12/30

3:05 pm-9:28 pm

1 stop6h 23m

$698

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sun 4/4

6:00 am-11:39 am

1 stop6h 39m

Winnipeg

Sun 4/4

2:15 pm-9:33 pm

1 stop6h 18m

$933

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 4/3

6:00 am-11:39 am

1 stop6h 39m

Winnipeg

Sat 4/3

2:15 pm-11:16 pm

1 stop8h 01m

$933

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 12/26

8:15 am-12:44 am

2 stops16h 29m

Winnipeg

Wed 12/30

6:25 am-11:00 pm

2 stops16h 35m

$1,153

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 12/26

5:30 am-11:31 am

1 stop6h 01m

Winnipeg

Mon 12/28

10:35 am-11:59 pm

2 stops13h 24m

$1,173

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 Boston to Winnipeg

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

Layovers

What is the typical price of a round-trip flight between Boston and Winnipeg?

Prices are currently low for flights on this route.

Typical prices usually range from $528 to $786.
The lowest price recently found on this route was $396.

What is the cheapest month to fly to Winnipeg?

In general, September is the cheapest month to fly from Boston to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $364. If you’re not able to fly to Winnipeg in September, then October is your next best option. Flight prices from Boston to Winnipeg during October average around $366.

How have Boston to Winnipeg flight prices changed over time?

As of November 2026, prices for Boston to Winnipeg flights are approximately 218% more expensive when compared to flights at the same time last year.

When to book flights from Boston to Winnipeg

Are you open to changing your travel dates? Check out the ideal times to fly from Boston to Winnipeg according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Boston to Winnipeg (BOS to YWG) flight deals and tips

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

Best Price Found	$203
Fastest flight time	6h 00m
Direct flights	None

The best one-way flight to Winnipeg from Boston in the past 72 hours is $203. The best round-trip flight deal from Boston to Winnipeg found on momondo in the last 72 hours is $409.

The fastest flight from Boston to Winnipeg takes 6h 00m

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

Search flight deals

Frequently asked questions about flying from Boston to Winnipeg

How far is Boston Logan Intl to Winnipeg by plane?
The straight-line distance from Boston Logan Intl to Winnipeg is 1343.0 mi. Flights usually cover this in 6h 00m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Boston Logan Intl Airport to Winnipeg Airport?
Prices for flights from Boston Logan Intl Airport to Winnipeg Airport are updated daily.
How many operators does momondo search for flights from Boston Logan Intl Airport to Winnipeg Airport?
As of November 2026, there are 4 operators available to choose from for flights from Boston Logan Intl Airport to Winnipeg Airport.
How old do you have to be to fly from Boston Logan Intl Airport to Winnipeg Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Boston Logan Intl Airport to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The travel and health documents required for your trip to Winnipeg Airport 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 Winnipeg Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Boston to Winnipeg?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Boston to Winnipeg is Air Canada (57% of total bookings). The next most popular airlines are Porter Airlines (20%), Delta (14%), and United Airlines (10%).

Best airlines flying from Boston to Winnipeg

Compare and see reviews for airlines that fly from Boston to Winnipeg with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $111	Free Cancellation	Rating 7.3 10,487 reviews	Search United Airlines flights
Air Canada	PriceFrom $204	Free Cancellation	Rating 7.1 11,894 reviews	Search Air Canada flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.8 8,721 reviews	Search Delta flights
Porter Airlines	PriceFrom $352	Free Cancellation	Rating 8.0 468 reviews	Search Porter Airlines flights

Selkirk

Portage la Prairie

Morden

Why use momondo?

Why should I use momondo to find a flight deal from Boston to Winnipeg?

It is quick and easy to find Boston to Winnipeg flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Winnipeg that suits you.

Can I find flights from Boston to Winnipeg with flexible booking policies on momondo?

Flights from Boston to Winnipeg with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Boston to Winnipeg?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Winnipeg from Boston.

I’m not ready to book a flight from Boston to Winnipeg right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Winnipeg, momondo offers a useful price alert feature which will track prices for flights to Winnipeg from Boston and alert you when they change.