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 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.

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 61% 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 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.

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

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

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 September 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.

$107 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

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Cheap round-trip flights

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

6h 15m1 stop Toronto Pearson Intl

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

6h 56m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl

$242Multiple Airlines

Fri, Oct 2 - Sun, Oct 11

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

6h 15m1 stop Toronto Pearson Intl

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

5h 31m1 stop Montreal Pierre Elliott Trudeau Intl

$243Multiple Airlines

Fri, Oct 2 - Sun, Oct 11

3:35 pm - 11:47 pmBOS Boston Logan Intl-YWG Winnipeg

9h 12m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

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

6h 56m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl

$257Air Canada

Fri, Oct 2 - Sun, Oct 11

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

7h 37m1 stop Chicago O'Hare Intl

2:00 pm - 9:59 pmYWG Winnipeg-BOS Boston Logan Intl

6h 59m1 stop Chicago O'Hare Intl

$299United Airlines

Thu, Oct 22 - Sat, Oct 24

10:50 am - 4:27 pmBOS Boston Logan Intl-YWG Winnipeg

6h 37m1 stop Toronto Pearson Intl

8:15 am - 4:05 pmYWG Winnipeg-BOS Boston Logan Intl

6h 50m1 stop Toronto Pearson Intl

$301Air Canada

Thu, Oct 22 - Sat, Oct 24

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

5h 55m1 stop Ottawa

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

8h 52m2 stops Ottawa Toronto Island

$304Porter Airlines

Wed, Nov 11 - Wed, Nov 18

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

11h 10m2 stops Toronto Island Ottawa

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

8h 52m2 stops Ottawa Toronto Island

$313Porter Airlines

Wed, Nov 11 - Wed, Nov 18

6:00 am - 12:23 pmBOS Boston Logan Intl-YWG Winnipeg

7h 23m1 stop Chicago O'Hare Intl

2:15 pm - 11:35 pmYWG Winnipeg-BOS Boston Logan Intl

8h 20m1 stop Chicago O'Hare Intl

$319United Airlines

Wed, Nov 11 - Wed, Nov 18

3:00 pm - 11:34 pmBOS Boston Logan Intl-YWG Winnipeg

9h 34m1 stop Minneapolis St Paul

12:30 pm - 11:53 pmYWG Winnipeg-BOS Boston Logan Intl

10h 23m1 stop Minneapolis St Paul

$338Delta

Mon, Mar 1 - Tue, Mar 9

5:50 am - 11:48 amBOS Boston Logan Intl-YWG Winnipeg

6h 58m1 stop Minneapolis St Paul

5:40 pm - 12:20 amYWG Winnipeg-BOS Boston Logan Intl

5h 40m1 stop Minneapolis St Paul

$350Delta

Thu, Oct 29 - Fri, Nov 6

Cheap last minute flights

Enter your travel dates to find the best prices.

6:00 am - 11:52 amBOS Boston Logan Intl-YWG Winnipeg

6h 52m1 stop Chicago O'Hare Intl

5:00 am - 11:51 amYWG Winnipeg-BOS Boston Logan Intl

5h 51m1 stop Toronto Pearson Intl

$415Multiple Airlines

Wed, Sep 23 - Wed, Sep 30

7:20 am - 8:57 pmBOS Boston Logan Intl-YWG Winnipeg

14h 37m2 stops Los Angeles Denver Intl

5:00 am - 11:51 amYWG Winnipeg-BOS Boston Logan Intl

5h 51m1 stop Toronto Pearson Intl

$420Multiple Airlines

Wed, Sep 23 - Wed, Sep 30

10:38 am - 8:57 pmBOS Boston Logan Intl-YWG Winnipeg

11h 19m2 stops Chicago O'Hare Intl Denver Intl

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

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

$432United Airlines

Wed, Sep 23 - Wed, Sep 30

7:10 pm - 4:25 pmBOS Boston Logan Intl-YWG Winnipeg

22h 15m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl

9:25 am - 6:35 pmYWG Winnipeg-BOS Boston Logan Intl

8h 10m1 stop Toronto Pearson Intl

$663Multiple Airlines

Sat, Sep 19 - Mon, Sep 28

2:20 pm - 10:43 amBOS Boston Logan Intl-YWG Winnipeg

21h 23m1 stop Ottawa

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

14h 55m1 stop Toronto Pearson Intl

$708Multiple Airlines

Sat, Sep 19 - Mon, Sep 28

9:41 am - 6:55 pmBOS Boston Logan Intl-YWG Winnipeg

34h 14m2 stops Mexico City Benito Juarez Cancun

8:10 pm - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

11h 55m1 stop Toronto Pearson Intl

$798Multiple Airlines

Fri, Sep 18 - Fri, Sep 25

10:05 am - 7:25 pmBOS Boston Logan Intl-YWG Winnipeg

10h 20m1 stop Toronto Pearson Intl

8:10 pm - 9:05 amYWG Winnipeg-BOS Boston Logan Intl

11h 55m1 stop Toronto Pearson Intl

$820Multiple Airlines

Fri, Sep 18 - Fri, Sep 25

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

11h 58m2 stops Toronto Island Ottawa

4:15 pm - 1:40 pmYWG Winnipeg-BOS Boston Logan Intl

20h 25m2 stops Ottawa Toronto Island

$958Porter Airlines

Sat, Sep 19 - Mon, Sep 28

2:20 pm - 12:55 amBOS Boston Logan Intl-YWG Winnipeg

11h 35m2 stops Ottawa Toronto Island

7:10 pm - 3:57 pmYWG Winnipeg-BOS Boston Logan Intl

19h 47m3 stops Calgary Edmonton Ottawa

$961Multiple Airlines

Wed, Sep 23 - Wed, Sep 30

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

11h 58m2 stops Toronto Island Ottawa

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

15h 50m2 stops Ottawa Toronto Pearson Intl

$1,007Porter Airlines

Fri, Sep 18 - Fri, Sep 25

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Delta flights from Boston to Winnipeg

Our best Delta deals on Boston to Winnipeg flight tickets

Delta

Oct 29

BOS5:50 amBoston Logan Intl

6h 58m

1 stop

YWG11:48 amWinnipeg

Nov 6

YWG5:40 pmWinnipeg

5h 40m

1 stop

BOS12:20 amBoston Logan Intl

$350

Delta

Mar 1

BOS3:00 pmBoston Logan Intl

9h 34m

1 stop

YWG11:34 pmWinnipeg

Mar 9

YWG12:30 pmWinnipeg

10h 23m

1 stop

BOS11:53 pmBoston Logan Intl

$355

Delta

Mar 1

BOS3:00 pmBoston Logan Intl

9h 34m

1 stop

YWG11:34 pmWinnipeg

Mar 9

YWG12:30 pmWinnipeg

10h 23m

1 stop

BOS11:53 pmBoston Logan Intl

$381

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets

Air Canada

Oct 2

BOS3:35 pmBoston Logan Intl

9h 12m

2 stops

YWG11:47 pmWinnipeg

Oct 11

YWG1:30 pmWinnipeg

6h 56m

2 stops

BOS9:26 pmBoston Logan Intl

$257

Air Canada

Oct 22

BOS10:50 amBoston Logan Intl

6h 37m

1 stop

YWG4:27 pmWinnipeg

Oct 24

YWG8:15 amWinnipeg

6h 50m

1 stop

BOS4:05 pmBoston Logan Intl

$301

Air Canada

Oct 22

BOS5:50 amBoston Logan Intl

11h 37m

2 stops

YWG4:27 pmWinnipeg

Oct 24

YWG5:00 amWinnipeg

5h 50m

1 stop

BOS11:50 amBoston Logan Intl

$310

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 10/2

10:05 am-3:20 pm

1 stop6h 15m

Winnipeg

Sun 10/11

1:30 pm-9:26 pm

2 stops6h 56m

$242

Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 10/2

10:05 am-3:20 pm

1 stop6h 15m

Winnipeg

Sun 10/11

8:10 am-2:41 pm

1 stop5h 31m

$243

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 10/2

3:35 pm-11:47 pm

2 stops9h 12m

Winnipeg

Sun 10/11

1:30 pm-9:26 pm

2 stops6h 56m

$257

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 10/22

6:00 am-12:37 pm

1 stop7h 37m

Winnipeg

Sat 10/24

2:00 pm-9:59 pm

1 stop6h 59m

$299

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 10/22

10:50 am-4:27 pm

1 stop6h 37m

Winnipeg

Sat 10/24

8:15 am-4:05 pm

1 stop6h 50m

$301

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 11/11

1:15 pm-6:10 pm

1 stop5h 55m

Winnipeg

Wed 11/18

11:40 am-9:32 pm

2 stops8h 52m

$304

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 11/11

8:00 am-6:10 pm

2 stops11h 10m

Winnipeg

Wed 11/18

11:40 am-9:32 pm

2 stops8h 52m

$313

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 11/11

6:00 am-12:23 pm

1 stop7h 23m

Winnipeg

Wed 11/18

2:15 pm-11:35 pm

1 stop8h 20m

$319

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 3/1

3:00 pm-11:34 pm

1 stop9h 34m

Winnipeg

Tue 3/9

12:30 pm-11:53 pm

1 stop10h 23m

$338

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 10/29

5:50 am-11:48 am

1 stop6h 58m

Winnipeg

Fri 11/6

5:40 pm-12:20 am

1 stop5h 40m

$350

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 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 August is your next best option. Flight prices from Boston to Winnipeg during August average around $437.

How have Boston to Winnipeg flight prices changed over time?

As of September 2026, prices for Boston to Winnipeg flights are approximately 18% 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	$107
Fastest flight time	5h 55m
Direct flights	None

The best one-way flight to Winnipeg from Boston in the past 72 hours is $107. The best round-trip flight deal from Boston to Winnipeg found on momondo in the last 72 hours is $242.

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 September 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 (61% of total bookings). The next most popular airlines are Porter Airlines (16%), Delta (13%), 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 7.4 10,214 reviews	Search United Airlines flights
Air Canada	PriceFrom $204	Free Cancellation	Rating 7.1 11,641 reviews	Search Air Canada flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.8 8,579 reviews	Search Delta flights
Porter Airlines	PriceFrom $352	Free Cancellation	Rating 8.0 462 reviews	Search Porter Airlines flights

Selkirk

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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.