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

Flights via Chicago (ORD) offer the lowest average round-trip price of $354.

What is the cheapest airline that flies from Boston Logan Intl to Winnipeg?

WestJet, Porter Airlines, and United Airlines are the most popular carriers operating from Boston Logan Intl to Winnipeg

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

Montreal (YUL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

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 62% 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 layover airport has the shortest connection time from Boston to Winnipeg?

Chicago (ORD) has the shortest average layover time for this route: 1h 21m.

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

Flights connecting via Toronto (YYZ) have the shortest average one-way travel time: 6h 12m.

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 August 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.

$135 Cheap Flights from Boston to Winnipeg in 2026

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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.

6:30 pm - 12:15 pmBOS Boston Logan Intl-YWG Winnipeg

18h 45m1 stop Calgary

9:05 pm - 5:40 pmYWG Winnipeg-BOS Boston Logan Intl

19h 35m1 stop Calgary

$331WestJet

Sat, Oct 3 - Mon, Oct 12

6:30 pm - 12:15 pmBOS Boston Logan Intl-YWG Winnipeg

18h 45m1 stop Calgary

4:25 pm - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

15h 40m1 stop Toronto Pearson Intl

$334Multiple Airlines

Fri, Oct 2 - Sun, Oct 4

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

6h 14m1 stop Toronto Pearson Intl

12:15 pm - 6:35 pmYWG Winnipeg-BOS Boston Logan Intl

5h 20m1 stop Toronto Pearson Intl

$338Porter Airlines

Mon, Aug 31 - Wed, Sep 2

10:05 am - 8:20 pmBOS Boston Logan Intl-YWG Winnipeg

11h 15m1 stop Toronto Pearson Intl

11:15 am - 3:15 pmYWG Winnipeg-BOS Boston Logan Intl

27h 00m2 stops Montreal St Hubert Toronto Island

$338Multiple Airlines

Sat, Oct 3 - Mon, Oct 12

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

11h 48m2 stops Toronto Island Ottawa

12:15 pm - 6:35 pmYWG Winnipeg-BOS Boston Logan Intl

5h 20m1 stop Toronto Pearson Intl

$341Porter Airlines

Mon, Aug 31 - Wed, Sep 2

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

6h 14m1 stop Toronto Pearson Intl

11:15 am - 10:30 amYWG Winnipeg-BOS Boston Logan Intl

22h 15m2 stops Montreal St Hubert Toronto Island

$343Porter Airlines

Thu, Sep 10 - Mon, Sep 14

10:35 am - 4:38 pmBOS Boston Logan Intl-YWG Winnipeg

7h 03m1 stop Montreal Pierre Elliott Trudeau Intl

8:05 am - 2:53 pmYWG Winnipeg-BOS Boston Logan Intl

5h 48m1 stop Montreal Pierre Elliott Trudeau Intl

$344Air Canada

Fri, Nov 6 - Fri, Nov 13

5:00 pm - 11:07 pmBOS Boston Logan Intl-YWG Winnipeg

7h 07m1 stop Toronto Pearson Intl

8:10 am - 2:41 pmYWG Winnipeg-BOS Boston Logan Intl

5h 31m1 stop Montreal Pierre Elliott Trudeau Intl

$349Air Canada

Fri, Oct 2 - Sun, Oct 4

6:01 am - 11:52 amBOS Boston Logan Intl-YWG Winnipeg

6h 51m1 stop Chicago O'Hare Intl

2:00 pm - 1:11 amYWG Winnipeg-BOS Boston Logan Intl

10h 11m1 stop Chicago O'Hare Intl

$415United Airlines

Fri, Aug 28 - Sun, Aug 30

3:13 pm - 10:33 pmBOS Boston Logan Intl-YWG Winnipeg

8h 20m1 stop Chicago O'Hare Intl

2:00 pm - 11:59 pmYWG Winnipeg-BOS Boston Logan Intl

8h 59m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

$424United Airlines

Thu, Sep 10 - Mon, Sep 14

Cheap last minute flights

Enter your travel dates to find the best prices.

8:30 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

13h 10m1 stop Toronto Island

5:10 pm - 10:30 amYWG Winnipeg-BOS Boston Logan Intl

16h 20m1 stop Toronto Pearson Intl

$602Multiple Airlines

Wed, Aug 12 - Thu, Aug 13

3:55 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

17h 45m2 stops Ottawa Toronto Pearson Intl

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

14h 55m1 stop Toronto Pearson Intl

$616Multiple Airlines

Wed, Aug 12 - Thu, Aug 13

3:55 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

17h 45m2 stops Ottawa Toronto Island

8:10 pm - 10:30 amYWG Winnipeg-BOS Boston Logan Intl

13h 20m1 stop Toronto Pearson Intl

$624Multiple Airlines

Mon, Aug 10 - Wed, Aug 12

3:55 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

17h 45m2 stops Ottawa Toronto Pearson Intl

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

14h 55m1 stop Toronto Pearson Intl

$627Multiple Airlines

Tue, Aug 11 - Thu, Aug 13

7:45 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

13h 55m1 stop Toronto Pearson Intl

8:10 pm - 10:30 amYWG Winnipeg-BOS Boston Logan Intl

13h 20m1 stop Toronto Pearson Intl

$628Multiple Airlines

Mon, Aug 10 - Wed, Aug 12

8:30 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

13h 10m1 stop Toronto Island

9:25 am - 7:50 pmYWG Winnipeg-BOS Boston Logan Intl

9h 25m1 stop Toronto Pearson Intl

$629Multiple Airlines

Tue, Aug 11 - Thu, Aug 13

8:30 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

13h 10m1 stop Toronto Island

8:10 pm - 10:30 amYWG Winnipeg-BOS Boston Logan Intl

13h 20m1 stop Toronto Pearson Intl

$632Multiple Airlines

Tue, Aug 11 - Wed, Aug 12

3:55 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

17h 45m2 stops Ottawa Toronto Pearson Intl

8:10 pm - 10:30 amYWG Winnipeg-BOS Boston Logan Intl

13h 20m1 stop Toronto Pearson Intl

$635Multiple Airlines

Tue, Aug 11 - Wed, Aug 12

3:55 pm - 8:40 amBOS Boston Logan Intl-YWG Winnipeg

17h 45m2 stops Ottawa Toronto Pearson Intl

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

8h 30m1 stop Toronto Pearson Intl

$635Multiple Airlines

Mon, Aug 10 - Thu, Aug 20

3:55 pm - 10:20 amBOS Boston Logan Intl-YWG Winnipeg

19h 25m3 stops Ottawa Toronto Pearson Intl Montreal St Hubert

4:15 pm - 10:30 amYWG Winnipeg-BOS Boston Logan Intl

17h 15m2 stops Ottawa Toronto Island

$774Porter Airlines

Tue, Aug 11 - Wed, Aug 12

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Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets

Porter Airlines

Aug 31

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Sep 2

YWG12:15 pmWinnipeg

5h 20m

1 stop

BOS6:35 pmBoston Logan Intl

$338

Porter Airlines

Aug 31

BOS7:10 amBoston Logan Intl

11h 48m

2 stops

YWG5:58 pmWinnipeg

Sep 2

YWG12:15 pmWinnipeg

5h 20m

1 stop

BOS6:35 pmBoston Logan Intl

$341

Porter Airlines

Sep 10

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Sep 14

YWG11:15 amWinnipeg

22h 15m

2 stops

BOS10:30 amBoston Logan Intl

$343

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets

Air Canada

Nov 6

BOS10:35 amBoston Logan Intl

7h 03m

1 stop

YWG4:38 pmWinnipeg

Nov 13

YWG8:05 amWinnipeg

5h 48m

1 stop

BOS2:53 pmBoston Logan Intl

$344

Air Canada

Aug 29

BOS10:50 amBoston Logan Intl

6h 30m

1 stop

YWG4:20 pmWinnipeg

Sep 5

YWG10:55 amWinnipeg

6h 12m

1 stop

BOS6:07 pmBoston Logan Intl

$349

Air Canada

Oct 3

BOS10:40 amBoston Logan Intl

5h 29m

1 stop

YWG3:09 pmWinnipeg

Oct 4

YWG8:10 amWinnipeg

5h 31m

1 stop

BOS2:41 pmBoston Logan Intl

$407

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 10/3

6:30 pm-12:15 pm

1 stop18h 45m

Winnipeg

Mon 10/12

9:05 pm-5:40 pm

1 stop19h 35m

$331

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 10/2

6:30 pm-12:15 pm

1 stop18h 45m

Winnipeg

Sun 10/4

4:25 pm-9:05 am

1 stop15h 40m

$334

Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 8/31

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Wed 9/2

12:15 pm-6:35 pm

1 stop5h 20m

$338

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 10/3

10:05 am-8:20 pm

1 stop11h 15m

Winnipeg

Mon 10/12

11:15 am-3:15 pm

2 stops27h 00m

$338

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 8/31

7:10 am-5:58 pm

2 stops11h 48m

Winnipeg

Wed 9/2

12:15 pm-6:35 pm

1 stop5h 20m

$341

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 9/10

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Mon 9/14

11:15 am-10:30 am

2 stops22h 15m

$343

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 11/6

10:35 am-4:38 pm

1 stop7h 03m

Winnipeg

Fri 11/13

8:05 am-2:53 pm

1 stop5h 48m

$344

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 10/2

5:00 pm-11:07 pm

1 stop7h 07m

Winnipeg

Sun 10/4

8:10 am-2:41 pm

1 stop5h 31m

$349

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 8/28

6:01 am-11:52 am

1 stop6h 51m

Winnipeg

Sun 8/30

2:00 pm-1:11 am

1 stop10h 11m

$415

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 9/10

3:13 pm-10:33 pm

1 stop8h 20m

Winnipeg

Mon 9/14

2:00 pm-11:59 pm

2 stops8h 59m

$424

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 $411 to $706.
The lowest price recently found on this route was $331.

What is the cheapest month to fly to Winnipeg?

In general, May 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 $517. If you’re not able to fly to Winnipeg in May, then October is your next best option. Flight prices from Boston to Winnipeg during October average around $519.

How have Boston to Winnipeg flight prices changed over time?

As of August 2026, prices for Boston to Winnipeg flights are approximately 27% cheaper 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

Fastest flight time	5h 55m
Direct flights	None

The fastest flight from Boston to Winnipeg takes 5h 55m

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 5h 55m, 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 August 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 (62% of total bookings). The next most popular airlines are Porter Airlines (14%), Delta (12%), and United Airlines (11%).

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 7.4 10,080 reviews	Search United Airlines flights
Air Canada	PriceFrom $204	Free Cancellation	Rating 7.1 11,434 reviews	Search Air Canada flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.8 8,499 reviews	Search Delta flights
Porter Airlines	PriceFrom $352	Free Cancellation	Rating 8.0 450 reviews	Search Porter Airlines flights

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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.