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.

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

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

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.

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 68% 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 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.

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 December 2025, 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.

$102 Cheap Flights from Boston to Winnipeg in 2025/26

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6:00 am - 3:07 pm

BOS

YWG

10h 07m1 stop

2:40 pm - 1:13 am

YWG

BOS

33h 33m2 stops

$264Multiple Airlines

Fri, Jan 23 - Fri, Jan 30

6:00 am - 3:07 pm

BOS

YWG

10h 07m1 stop

7:30 am - 1:13 am

YWG

BOS

16h 43m1 stop

$270Multiple Airlines

Fri, Jan 23 - Fri, Jan 30

3:43 pm - 12:44 pm

BOS

YWG

22h 01m3 stops

7:30 am - 11:19 pm

YWG

BOS

14h 49m2 stops

$330Multiple Airlines

Fri, Jan 23 - Fri, Jan 30

3:43 pm - 12:44 pm

BOS

YWG

22h 01m3 stops

12:55 pm - 4:19 pm

YWG

BOS

26h 24m3 stops

$363Multiple Airlines

Fri, Jan 23 - Fri, Jan 30

5:34 am - 8:28 pm

BOS

YWG

15h 54m2 stops

7:30 am - 11:19 pm

YWG

BOS

14h 49m2 stops

$370Multiple Airlines

Fri, Jan 23 - Fri, Jan 30

10:15 am - 4:35 pm

BOS

YWG

7h 20m1 stop

8:15 am - 2:52 pm

YWG

BOS

5h 37m1 stop

$559Air Canada

Mon, Jan 12 - Tue, Jan 13

5:30 am - 10:16 am

BOS

YWG

5h 46m1 stop

8:15 am - 2:52 pm

YWG

BOS

5h 37m1 stop

$560Air Canada

Mon, Jan 12 - Tue, Jan 13

10:15 am - 4:35 pm

BOS

YWG

7h 20m1 stop

6:00 am - 2:52 pm

YWG

BOS

7h 52m2 stops

$564Air Canada

Mon, Jan 12 - Tue, Jan 13

5:30 am - 10:16 am

BOS

YWG

5h 46m1 stop

6:00 am - 2:52 pm

YWG

BOS

7h 52m2 stops

$565Air Canada

Mon, Jan 12 - Tue, Jan 13

10:15 am - 8:28 pm

BOS

YWG

11h 13m2 stops

6:00 am - 2:52 pm

YWG

BOS

7h 52m2 stops

$570Air Canada

Mon, Jan 12 - Tue, Jan 13

United Airlines flights from Boston to Winnipeg

Our best United Airlines deals on Boston to Winnipeg flight tickets

United Airlines

Feb 3

BOS6:00 amBoston Logan Intl

6h 57m

1 stop

YWG11:57 amWinnipeg

Feb 7

YWG2:20 pmWinnipeg

8h 29m

2 stops

BOS11:49 pmBoston Logan Intl

$577

Find similar

United Airlines

Feb 3

BOS9:30 amBoston Logan Intl

27h 27m

2 stops

YWG11:57 amWinnipeg

Feb 7

YWG2:20 pmWinnipeg

19h 16m

2 stops

BOS10:36 amBoston Logan Intl

$582

Find similar

United Airlines

Dec 23

BOS6:01 amBoston Logan Intl

6h 56m

1 stop

YWG11:57 amWinnipeg

Dec 30

YWG8:40 amWinnipeg

12h 35m

1 stop

BOS10:15 pmBoston Logan Intl

$675

Find similar

American Airlines flights from Boston to Winnipeg

Our best American Airlines deals on Boston to Winnipeg flight tickets

American Airlines

Dec 23

BOS10:55 amBoston Logan Intl

13h 40m

2 stops

YWG11:35 pmWinnipeg

Dec 30

YWG6:00 amWinnipeg

12h 56m

3 stops

BOS7:56 pmBoston Logan Intl

$1,260

Find similar

American Airlines

Dec 23

BOS2:04 pmBoston Logan Intl

10h 31m

2 stops

YWG11:35 pmWinnipeg

Dec 30

YWG6:00 amWinnipeg

14h 11m

3 stops

BOS9:11 pmBoston Logan Intl

$1,413

Find similar

American Airlines

Dec 19

BOS6:00 amBoston Logan Intl

18h 35m

3 stops

YWG11:35 pmWinnipeg

Dec 22

YWG6:00 amWinnipeg

13h 26m

2 stops

BOS8:26 pmBoston Logan Intl

$1,464

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 1/23

6:00 am-3:07 pm

1 stop10h 07m

Winnipeg

Fri 1/30

2:40 pm-1:13 am

2 stops33h 33m

$264

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 1/23

6:00 am-3:07 pm

1 stop10h 07m

Winnipeg

Fri 1/30

7:30 am-1:13 am

1 stop16h 43m

$270

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 1/23

3:43 pm-12:44 pm

3 stops22h 01m

Winnipeg

Fri 1/30

7:30 am-11:19 pm

2 stops14h 49m

$330

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 1/23

3:43 pm-12:44 pm

3 stops22h 01m

Winnipeg

Fri 1/30

12:55 pm-4:19 pm

3 stops26h 24m

$363

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 1/23

5:34 am-8:28 pm

2 stops15h 54m

Winnipeg

Fri 1/30

7:30 am-11:19 pm

2 stops14h 49m

$370

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 1/12

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

Tue 1/13

8:15 am-2:52 pm

1 stop5h 37m

$559

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 1/12

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

Tue 1/13

8:15 am-2:52 pm

1 stop5h 37m

$560

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 1/12

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

Tue 1/13

6:00 am-2:52 pm

2 stops7h 52m

$564

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 1/12

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

Tue 1/13

6:00 am-2:52 pm

2 stops7h 52m

$565

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 1/12

10:15 am-8:28 pm

2 stops11h 13m

Winnipeg

Tue 1/13

6:00 am-2:52 pm

2 stops7h 52m

$570

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 $233. If you’re not able to fly to Winnipeg in July, then August is your next best option. Flight prices from Boston to Winnipeg during August average around $399.

What is the cheapest day to depart on your flight to Winnipeg?

The cheapest day to depart on your flight to Winnipeg is on a Sunday when prices can be found for as low as $354. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Boston because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $789.

What is the cheapest time of day to depart on your flight to Winnipeg?

The cheapest time of day to fly to Winnipeg is at noon when flights can be purchased for as low as $405. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $552 on average. Flights to Winnipeg from Boston in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

How far in advance should I book a flight 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 $463 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 $303 on momondo.

How have Boston to Winnipeg flight prices changed over time?

As of December 2025, prices for Boston to Winnipeg flights are approximately 2% 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 37m
Direct flights	None

The fastest flight from Boston to Winnipeg takes 5h 37m

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 5h 37m, 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 December 2025, 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 (68% of total bookings). The next most popular airlines are Delta (18%) and United Airlines (14%).

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 $134	Free Cancellation	Rating 7.1 10,513 reviews	Search Air Canada flights
United Airlines	PriceFrom $172	Free Cancellation	Rating 7.4 9,092 reviews	Search United Airlines flights
Delta	PriceFrom $228	Free Cancellation	Rating 7.9 8,007 reviews	Search Delta 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.