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 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 62% 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 has the shortest connection time from Boston to Winnipeg?

Chicago (ORD) has the shortest average layover time for this route: 1h 21m.

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.

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

Delta and WestJet 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 March 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.

$128 Cheap Flights from Boston to Winnipeg in 2026

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Find the cheapest flights from Boston to Winnipeg

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One-way

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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

$260Porter Airlines

Wed, May 27 - Tue, Jun 2

5:30 am - 8:17 pm

BOS

YWG

15h 47m

2 stops

5:30 am - 12:11 pm

YWG

BOS

5h 41m

1 stop

$283Air Canada

Mon, Apr 13 - Mon, Apr 20

6:40 pm - 10:09 am

BOS

YWG

16h 29m

1 stop

5:30 am - 12:11 pm

YWG

BOS

5h 41m

1 stop

$286Air Canada

Mon, Apr 13 - Mon, Apr 20

10:05 am - 5:58 pm

BOS

YWG

8h 53m

2 stops

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$288Porter Airlines

Wed, May 27 - Tue, Jun 2

5:30 am - 8:17 pm

BOS

YWG

15h 47m

2 stops

5:30 am - 2:52 pm

YWG

BOS

8h 22m

2 stops

$293Air Canada

Mon, Apr 13 - Mon, Apr 20

10:05 am - 5:58 pm

BOS

YWG

8h 53m

2 stops

9:20 am - 8:55 pm

YWG

BOS

10h 35m

2 stops

$304Porter Airlines

Wed, May 27 - Tue, Jun 2

5:10 am - 11:08 am

BOS

YWG

6h 58m

1 stop

8:00 am - 2:47 pm

YWG

BOS

5h 47m

1 stop

$307Air Canada

Sun, May 3 - Sat, May 9

5:50 am - 11:01 am

BOS

YWG

6h 11m

1 stop

11:55 am - 7:35 pm

YWG

BOS

6h 40m

1 stop

$310Delta

Fri, Apr 10 - Tue, Apr 14

6:15 am - 12:33 pm

BOS

YWG

7h 18m

1 stop

5:30 am - 12:11 pm

YWG

BOS

5h 41m

1 stop

$312Air Canada

Mon, Apr 13 - Mon, Apr 20

5:25 pm - 11:52 am

BOS

YWG

19h 27m

2 stops

2:00 pm - 9:59 pm

YWG

BOS

6h 59m

1 stop

$320United Airlines

Mon, Apr 13 - Mon, Apr 20

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

6h 14m

1 stop

YWG3:19 pmWinnipeg

Jun 2

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$260

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

$288

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

$304

Delta flights from Boston to Winnipeg

Our best Delta deals on Boston to Winnipeg flight tickets

Delta

Apr 10

BOS5:50 amBoston Logan Intl

6h 11m

1 stop

YWG11:01 amWinnipeg

Apr 14

YWG11:55 amWinnipeg

6h 40m

1 stop

BOS7:35 pmBoston Logan Intl

$310

Delta

Mar 25

BOS8:05 amBoston Logan Intl

9h 18m

1 stop

YWG4:23 pmWinnipeg

Mar 27

YWG6:40 amWinnipeg

9h 24m

1 stop

BOS5:04 pmBoston Logan Intl

$515

Delta

Mar 13

BOS5:50 amBoston Logan Intl

6h 11m

1 stop

YWG11:01 amWinnipeg

Mar 17

YWG6:40 amWinnipeg

9h 24m

1 stop

BOS5:04 pmBoston Logan Intl

$638

Fly from

Fly to

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/27

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Tue 6/2

9:20 am-5:35 pm

1 stop7h 15m

$260

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 4/13

5:30 am-8:17 pm

2 stops15h 47m

Winnipeg

Mon 4/20

5:30 am-12:11 pm

1 stop5h 41m

$283

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 4/13

6:40 pm-10:09 am

1 stop16h 29m

Winnipeg

Mon 4/20

5:30 am-12:11 pm

1 stop5h 41m

$286

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

$288

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 4/13

5:30 am-8:17 pm

2 stops15h 47m

Winnipeg

Mon 4/20

5:30 am-2:52 pm

2 stops8h 22m

$293

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

$304

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 5/3

5:10 am-11:08 am

1 stop6h 58m

Winnipeg

Sat 5/9

8:00 am-2:47 pm

1 stop5h 47m

$307

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 4/10

5:50 am-11:01 am

1 stop6h 11m

Winnipeg

Tue 4/14

11:55 am-7:35 pm

1 stop6h 40m

$310

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 4/13

6:15 am-12:33 pm

1 stop7h 18m

Winnipeg

Mon 4/20

5:30 am-12:11 pm

1 stop5h 41m

$312

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 4/13

5:25 pm-11:52 am

2 stops19h 27m

Winnipeg

Mon 4/20

2:00 pm-9:59 pm

1 stop6h 59m

$320

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, May 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 $261. If you’re not able to fly to Winnipeg in May, then July is your next best option. Flight prices from Boston to Winnipeg during July average around $294.

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 $493 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 $302 on momondo.

How have Boston to Winnipeg flight prices changed over time?

As of March 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 39m
Direct flights	None

The fastest flight from Boston to Winnipeg takes 5h 39m

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 39m, 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 March 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 10,775 reviews	Search Air Canada flights
Delta	PriceFrom $131	Free Cancellation	Rating 7.9 8,245 reviews	Search Delta flights
United Airlines	PriceFrom $172	Free Cancellation	Rating 7.4 9,382 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.