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.

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 airlines fly to Winnipeg?

Air Canada, Delta and United Airlines 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 airport is the most popular layover for flights between Boston and Winnipeg?

Montreal (YUL) was the most common stop: 57% of momondo users choosing 1-stop flights on this route connected there.

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

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

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.

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 May 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.

$155 Cheap Flights from Boston to Winnipeg in 2026

Q: 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 $607 to $391. The lowest price recently found on this route was $277.

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Find the cheapest flights from Boston to Winnipeg

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10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$277Porter Airlines

Thu, Sep 17 - Thu, Sep 24

7:10 am - 5:58 pm

BOS

YWG

11h 48m

2 stops

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$280Porter Airlines

Thu, Sep 17 - Thu, Sep 24

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$302Porter Airlines

Thu, Oct 15 - Tue, Oct 20

10:20 am - 4:36 pm

BOS

YWG

7h 16m

1 stop

8:15 am - 4:57 pm

YWG

BOS

7h 42m

1 stop

$317Air Canada

Thu, Nov 5 - Wed, Nov 11

5:30 am - 10:16 am

BOS

YWG

5h 46m

1 stop

1:45 pm - 8:17 pm

YWG

BOS

5h 32m

1 stop

$318Air Canada

Fri, Oct 30 - Mon, Nov 2

10:50 am - 4:17 pm

BOS

YWG

6h 27m

1 stop

8:10 am - 2:41 pm

YWG

BOS

5h 31m

1 stop

$322Air Canada

Wed, Sep 9 - Sat, Sep 12

10:20 am - 4:36 pm

BOS

YWG

7h 16m

1 stop

6:00 am - 2:37 pm

YWG

BOS

7h 37m

2 stops

$323Air Canada

Thu, Nov 5 - Wed, Nov 11

7:45 am - 8:57 pm

BOS

YWG

14h 12m

1 stop

7:00 am - 2:07 pm

YWG

BOS

6h 07m

1 stop

$325United Airlines

Wed, Sep 9 - Sat, Sep 12

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$330Porter Airlines

Tue, Oct 13 - Wed, Oct 21

10:40 am - 3:09 pm

BOS

YWG

5h 29m

1 stop

12:20 pm - 9:27 pm

YWG

BOS

8h 07m

2 stops

$331Air Canada

Thu, Oct 15 - Wed, Oct 21

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets

Air Canada

Nov 5

BOS10:20 amBoston Logan Intl

7h 16m

1 stop

YWG4:36 pmWinnipeg

Nov 11

YWG8:15 amWinnipeg

7h 42m

1 stop

BOS4:57 pmBoston Logan Intl

$317

Air Canada

Oct 30

BOS5:30 amBoston Logan Intl

5h 46m

1 stop

YWG10:16 amWinnipeg

Nov 2

YWG1:45 pmWinnipeg

5h 32m

1 stop

BOS8:17 pmBoston Logan Intl

$318

Air Canada

Sep 9

BOS10:50 amBoston Logan Intl

6h 27m

1 stop

YWG4:17 pmWinnipeg

Sep 12

YWG8:10 amWinnipeg

5h 31m

1 stop

BOS2:41 pmBoston Logan Intl

$322

Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets

Porter Airlines

Sep 17

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Sep 24

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$277

Porter Airlines

Sep 17

BOS7:10 amBoston Logan Intl

11h 48m

2 stops

YWG5:58 pmWinnipeg

Sep 24

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$280

Porter Airlines

Oct 15

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Oct 20

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$302

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/17

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Thu 9/24

9:20 am-5:35 pm

1 stop7h 15m

$277

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/17

7:10 am-5:58 pm

2 stops11h 48m

Winnipeg

Thu 9/24

9:20 am-5:35 pm

1 stop7h 15m

$280

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/15

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Tue 10/20

9:20 am-5:35 pm

1 stop7h 15m

$302

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 11/5

10:20 am-4:36 pm

1 stop7h 16m

Winnipeg

Wed 11/11

8:15 am-4:57 pm

1 stop7h 42m

$317

Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 10/30

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

Mon 11/2

1:45 pm-8:17 pm

1 stop5h 32m

$318

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/9

10:50 am-4:17 pm

1 stop6h 27m

Winnipeg

Sat 9/12

8:10 am-2:41 pm

1 stop5h 31m

$322

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 11/5

10:20 am-4:36 pm

1 stop7h 16m

Winnipeg

Wed 11/11

6:00 am-2:37 pm

2 stops7h 37m

$323

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/9

7:45 am-8:57 pm

1 stop14h 12m

Winnipeg

Sat 9/12

7:00 am-2:07 pm

1 stop6h 07m

$325

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 10/13

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Wed 10/21

9:20 am-5:35 pm

1 stop7h 15m

$330

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/15

10:40 am-3:09 pm

1 stop5h 29m

Winnipeg

Wed 10/21

12:20 pm-9:27 pm

2 stops8h 07m

$331

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?

What is the cheapest month to fly to Winnipeg?

In general, August 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 $420. If you’re not able to fly to Winnipeg in August, then September is your next best option. Flight prices from Boston to Winnipeg during September average around $433.

How far in advance should I book a flight from Boston to Winnipeg?

You are more likely to see cheaper flights to Winnipeg from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Winnipeg for around $542 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Winnipeg from Boston for as low as $366 on momondo.

How have Boston to Winnipeg flight prices changed over time?

As of May 2026, prices for Boston to Winnipeg flights are approximately 151% 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	5h 34m
Direct flights	None

The fastest flight from Boston to Winnipeg takes 5h 34m

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

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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 34m, 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 May 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 Delta (16%), United Airlines (12%), and Porter 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
Delta	PriceFrom $143	Free Cancellation	Rating 7.9 8,454 reviews	Search Delta flights
United Airlines	PriceFrom $149	Free Cancellation	Rating 7.4 9,729 reviews	Search United Airlines flights
Air Canada	PriceFrom $194	Free Cancellation	Rating 7.1 11,047 reviews	Search Air Canada flights
Porter Airlines	PriceFrom $293	Free Cancellation	Rating 8.0 439 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.