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: 50% of momondo users choosing 1-stop flights on this route connected there.

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 is the most popular carrier operating from Boston Logan Intl to Winnipeg

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 66% 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 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 July 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.

$164 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 typical for flights on this route. Typical prices usually range from $320 to $634. The lowest price recently found on this route was $333.

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.

11:10 am - 8:40 am

BOS

YWG

22h 30m

1 stop

11:15 am - 10:30 am

YWG

BOS

22h 15m

2 stops

$333Multiple Airlines

Fri, Sep 4 - Sun, Sep 13

11:10 am - 8:40 am

BOS

YWG

22h 30m

1 stop

6:15 am - 4:46 pm

YWG

BOS

9h 31m

1 stop

$337Multiple Airlines

Fri, Sep 4 - Sun, Sep 13

11:10 am - 8:40 am

BOS

YWG

22h 30m

1 stop

11:15 am - 10:30 am

YWG

BOS

22h 15m

2 stops

$339Multiple Airlines

Fri, Sep 4 - Sun, Sep 13

11:10 am - 8:40 am

BOS

YWG

22h 30m

1 stop

7:45 am - 10:30 am

YWG

BOS

25h 45m

1 stop

$343Multiple Airlines

Fri, Sep 4 - Sun, Sep 13

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

11:15 am - 9:05 am

YWG

BOS

20h 50m

2 stops

$351Porter Airlines

Thu, Oct 8 - Sun, Oct 11

7:30 pm - 12:55 am

BOS

YWG

6h 25m

1 stop

8:45 pm - 9:05 am

YWG

BOS

11h 20m

1 stop

$353Multiple Airlines

Thu, Oct 8 - Sun, Oct 11

7:10 am - 5:58 pm

BOS

YWG

11h 48m

2 stops

7:45 am - 6:35 pm

YWG

BOS

9h 50m

1 stop

$357Multiple Airlines

Sat, Aug 22 - Tue, Sep 1

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

12:15 pm - 6:50 pm

YWG

BOS

5h 35m

1 stop

$359Porter Airlines

Thu, Jul 23 - Mon, Jul 27

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

12:15 pm - 6:50 pm

YWG

BOS

5h 35m

1 stop

$364Porter Airlines

Wed, Aug 12 - Thu, Aug 13

4:45 pm - 8:40 am

BOS

YWG

16h 55m

2 stops

4:15 pm - 9:05 am

YWG

BOS

15h 50m

2 stops

$368Multiple Airlines

Fri, Sep 4 - Sun, Sep 13

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Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets

Porter Airlines

Oct 8

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Oct 11

YWG11:15 amWinnipeg

20h 50m

2 stops

BOS9:05 amBoston Logan Intl

$351

Porter Airlines

Jul 23

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Jul 27

YWG12:15 pmWinnipeg

5h 35m

1 stop

BOS6:50 pmBoston Logan Intl

$359

Porter Airlines

Aug 12

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Aug 13

YWG12:15 pmWinnipeg

5h 35m

1 stop

BOS6:50 pmBoston Logan Intl

$364

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets

Air Canada

Jul 22

BOS5:45 amBoston Logan Intl

9h 40m

2 stops

YWG2:25 pmWinnipeg

Jul 26

YWG5:00 amWinnipeg

8h 02m

1 stop

BOS2:02 pmBoston Logan Intl

$381

Air Canada

Jul 22

BOS10:40 amBoston Logan Intl

8h 35m

2 stops

YWG6:15 pmWinnipeg

Jul 26

YWG5:00 amWinnipeg

8h 41m

2 stops

BOS2:41 pmBoston Logan Intl

$403

Air Canada

Oct 7

BOS6:00 amBoston Logan Intl

6h 12m

1 stop

YWG11:12 amWinnipeg

Oct 10

YWG8:10 amWinnipeg

5h 31m

1 stop

BOS2:41 pmBoston Logan Intl

$409

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 9/4

11:10 am-8:40 am

1 stop22h 30m

Winnipeg

Sun 9/13

11:15 am-10:30 am

2 stops22h 15m

$333

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 9/4

11:10 am-8:40 am

1 stop22h 30m

Winnipeg

Sun 9/13

6:15 am-4:46 pm

1 stop9h 31m

$337

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 9/4

11:10 am-8:40 am

1 stop22h 30m

Winnipeg

Sun 9/13

11:15 am-10:30 am

2 stops22h 15m

$339

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 9/4

11:10 am-8:40 am

1 stop22h 30m

Winnipeg

Sun 9/13

7:45 am-10:30 am

1 stop25h 45m

$343

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/8

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Sun 10/11

11:15 am-9:05 am

2 stops20h 50m

$351

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/8

7:30 pm-12:55 am

1 stop6h 25m

Winnipeg

Sun 10/11

8:45 pm-9:05 am

1 stop11h 20m

$353

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 8/22

7:10 am-5:58 pm

2 stops11h 48m

Winnipeg

Tue 9/1

7:45 am-6:35 pm

1 stop9h 50m

$357

Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 7/23

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Mon 7/27

12:15 pm-6:50 pm

1 stop5h 35m

$359

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 8/12

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Thu 8/13

12:15 pm-6:50 pm

1 stop5h 35m

$364

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 9/4

4:45 pm-8:40 am

2 stops16h 55m

Winnipeg

Sun 9/13

4:15 pm-9:05 am

2 stops15h 50m

$368

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 $434. 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 $438.

How have Boston to Winnipeg flight prices changed over time?

As of July 2026, prices for Boston to Winnipeg flights are approximately 14% 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.

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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 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 July 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 (66% of total bookings). The next most popular airlines are Delta (12%), United Airlines (11%), and Porter 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 $149	Free Cancellation	Rating 7.4 9,947 reviews	Search United Airlines flights
Air Canada	PriceFrom $194	Free Cancellation	Rating 7.1 11,321 reviews	Search Air Canada flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.8 8,451 reviews	Search Delta flights
Porter Airlines	PriceFrom $293	Free Cancellation	Rating 7.9 442 reviews	Search Porter Airlines flights

Selkirk

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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.