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

Montreal (YUL) was the most common stop: 80% of momondo users choosing 1-stop flights on this route connected there.

What airlines fly to Winnipeg?

Air Canada, United 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 63% of people opting to fly with this airline when traveling to Winnipeg. Keep in mind that there are 3 different airlines that fly to Winnipeg on a routine basis, so you have a few additional options to choose from.

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?

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

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: 6h 52m.

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 February 2026, there are 3 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.

$132 Cheap Flights from Boston to Winnipeg in 2026

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Find the cheapest flights from Boston to Winnipeg

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

5:10 am - 10:03 am

BOS

YWG

5h 53m

1 stop

8:00 am - 2:47 pm

YWG

BOS

5h 47m

1 stop

$307Air Canada

Wed, May 27 - Tue, Jun 2

5:30 am - 10:09 am

BOS

YWG

5h 39m

1 stop

5:30 am - 12:11 pm

YWG

BOS

5h 41m

1 stop

$329Air Canada

Sun, Apr 26 - Tue, Apr 28

10:05 am - 5:58 pm

BOS

YWG

8h 53m

2 stops

9:20 am - 8:55 pm

YWG

BOS

10h 35m

2 stops

$341Porter Airlines

Wed, May 27 - Tue, Jun 2

10:05 am - 5:58 pm

BOS

YWG

8h 53m

2 stops

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$343Porter Airlines

Wed, May 27 - Tue, Jun 2

3:30 pm - 7:35 pm

BOS

YWG

29h 05m

2 stops

7:30 am - 1:31 am

YWG

BOS

17h 01m

1 stop

$344Multiple Airlines

Wed, Apr 8 - Wed, Apr 15

5:30 am - 10:15 am

BOS

YWG

5h 45m

1 stop

5:30 am - 12:14 pm

YWG

BOS

5h 44m

1 stop

$415Air Canada

Fri, Mar 27 - Mon, Mar 30

3:30 pm - 11:13 am

BOS

YWG

20h 43m

1 stop

7:30 am - 1:31 am

YWG

BOS

17h 01m

1 stop

$421Multiple Airlines

Wed, Apr 8 - Wed, Apr 15

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$438Porter Airlines

Wed, Jul 1 - Sun, Jul 5

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$442Porter Airlines

Thu, Jul 2 - Mon, Jul 6

5:30 am - 10:15 am

BOS

YWG

5h 45m

1 stop

7:05 pm - 12:11 pm

YWG

BOS

16h 06m

1 stop

$455Air Canada

Tue, Mar 24 - Tue, Mar 31

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets

Air Canada

May 27

BOS5:10 amBoston Logan Intl

5h 53m

1 stop

YWG10:03 amWinnipeg

Jun 2

YWG8:00 amWinnipeg

5h 47m

1 stop

BOS2:47 pmBoston Logan Intl

$307

Air Canada

Apr 26

BOS5:30 amBoston Logan Intl

5h 39m

1 stop

YWG10:09 amWinnipeg

Apr 28

YWG5:30 amWinnipeg

5h 41m

1 stop

BOS12:11 pmBoston Logan Intl

$329

Air Canada

Mar 27

BOS5:30 amBoston Logan Intl

5h 45m

1 stop

YWG10:15 amWinnipeg

Mar 30

YWG5:30 amWinnipeg

5h 44m

1 stop

BOS12:14 pmBoston Logan Intl

$415

Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets

Porter Airlines

May 27

BOS10:05 amBoston Logan Intl

8h 53m

2 stops

YWG5:58 pmWinnipeg

Jun 2

YWG9:20 amWinnipeg

10h 35m

2 stops

BOS8:55 pmBoston Logan Intl

$341

Porter Airlines

May 27

BOS10:05 amBoston Logan Intl

8h 53m

2 stops

YWG5:58 pmWinnipeg

Jun 2

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$343

Porter Airlines

Jul 1

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Jul 5

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$438

Fly from

Fly to

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/27

5:10 am-10:03 am

1 stop5h 53m

Winnipeg

Tue 6/2

8:00 am-2:47 pm

1 stop5h 47m

$307

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 4/26

5:30 am-10:09 am

1 stop5h 39m

Winnipeg

Tue 4/28

5:30 am-12:11 pm

1 stop5h 41m

$329

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/27

10:05 am-5:58 pm

2 stops8h 53m

Winnipeg

Tue 6/2

9:20 am-8:55 pm

2 stops10h 35m

$341

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/27

10:05 am-5:58 pm

2 stops8h 53m

Winnipeg

Tue 6/2

9:20 am-5:35 pm

1 stop7h 15m

$343

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 4/8

3:30 pm-7:35 pm

2 stops29h 05m

Winnipeg

Wed 4/15

7:30 am-1:31 am

1 stop17h 01m

$344

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 3/27

5:30 am-10:15 am

1 stop5h 45m

Winnipeg

Mon 3/30

5:30 am-12:14 pm

1 stop5h 44m

$415

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 4/8

3:30 pm-11:13 am

1 stop20h 43m

Winnipeg

Wed 4/15

7:30 am-1:31 am

1 stop17h 01m

$421

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 7/1

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Sun 7/5

9:20 am-5:35 pm

1 stop7h 15m

$438

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 7/2

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Mon 7/6

9:20 am-5:35 pm

1 stop7h 15m

$442

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 3/24

5:30 am-10:15 am

1 stop5h 45m

Winnipeg

Tue 3/31

7:05 pm-12:11 pm

1 stop16h 06m

$455

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, July 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 $172. If you’re not able to fly to Winnipeg in July, then May is your next best option. Flight prices from Boston to Winnipeg during May average around $261.

How have Boston to Winnipeg flight prices changed over time?

As of February 2026, prices for Boston to Winnipeg flights are approximately 30% 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

Fastest flight time	6h 11m
Direct flights	None

The fastest flight from Boston to Winnipeg takes 6h 11m

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

Search flight deals

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 11m, 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 February 2026, there are 3 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 United Airlines (20%) and Delta (17%).

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
Air Canada	PriceFrom $128	Free Cancellation	Rating 7.1 10,742 reviews	Search Air Canada flights
Delta	PriceFrom $131	Free Cancellation	Rating 7.9 8,239 reviews	Search Delta flights
United Airlines	PriceFrom $172	Free Cancellation	Rating 7.4 9,344 reviews	Search United Airlines flights

Selkirk

Scanterbury

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.