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?

Delta and United Airlines are the most popular carriers 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 64% 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 travel time from Boston to Winnipeg?

Flights connecting via Montreal (YUL) have the shortest average one-way travel time: 6h 52m.

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.

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 April 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.

$168 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 $725 to $465. The lowest price recently found on this route was $360.

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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

$360Porter Airlines

Sat, May 23 - Sun, May 24

6:30 pm - 8:15 pm

BOS

YWG

26h 45m

1 stop

6:00 am - 5:40 pm

YWG

BOS

10h 40m

1 stop

$378WestJet

Fri, May 1 - Fri, May 8

10:35 am - 3:14 pm

BOS

YWG

5h 39m

1 stop

5:10 am - 11:46 am

YWG

BOS

5h 36m

1 stop

$386Air Canada

Thu, May 7 - Mon, May 11

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$391Porter Airlines

Sat, Jul 4 - Sat, Jul 11

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$392Porter Airlines

Fri, Jul 10 - Sat, Jul 18

10:35 am - 3:14 pm

BOS

YWG

5h 39m

1 stop

8:10 am - 9:27 pm

YWG

BOS

12h 17m

2 stops

$395Air Canada

Thu, May 7 - Mon, May 11

6:30 pm - 11:10 am

BOS

YWG

17h 40m

1 stop

7:00 am - 5:40 pm

YWG

BOS

9h 40m

1 stop

$398WestJet

Mon, May 25 - Wed, Jun 3

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$402Porter Airlines

Wed, May 27 - Wed, Jun 3

5:30 am - 10:09 am

BOS

YWG

5h 39m

1 stop

11:00 am - 6:07 pm

YWG

BOS

6h 07m

1 stop

$403Air Canada

Thu, Apr 30 - Sat, May 9

7:10 am - 5:58 pm

BOS

YWG

11h 48m

2 stops

9:20 am - 5:35 pm

YWG

BOS

7h 15m

1 stop

$404Porter Airlines

Wed, May 27 - Wed, Jun 3

Delta flights from Boston to Winnipeg

Our best Delta deals on Boston to Winnipeg flight tickets

Delta

May 2

BOS3:10 pmBoston Logan Intl

9h 20m

1 stop

YWG11:30 pmWinnipeg

May 8

YWG5:41 pmWinnipeg

5h 13m

1 stop

BOS11:54 pmBoston Logan Intl

$411

Delta

May 25

BOS5:51 amBoston Logan Intl

10h 04m

1 stop

YWG2:55 pmWinnipeg

Jun 1

YWG3:50 pmWinnipeg

7h 04m

1 stop

BOS11:54 pmBoston Logan Intl

$450

Delta

May 25

BOS5:51 amBoston Logan Intl

10h 04m

1 stop

YWG2:55 pmWinnipeg

Jun 3

YWG5:41 pmWinnipeg

5h 13m

1 stop

BOS11:54 pmBoston Logan Intl

$493

Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets

Porter Airlines

May 23

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

May 24

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$360

Porter Airlines

Jul 4

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Jul 11

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$391

Porter Airlines

Jul 10

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Jul 17

YWG9:20 amWinnipeg

7h 15m

1 stop

BOS5:35 pmBoston Logan Intl

$392

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 5/23

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Sun 5/24

9:20 am-5:35 pm

1 stop7h 15m

$360

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 5/1

6:30 pm-8:15 pm

1 stop26h 45m

Winnipeg

Fri 5/8

6:00 am-5:40 pm

1 stop10h 40m

$378

Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 5/7

10:35 am-3:14 pm

1 stop5h 39m

Winnipeg

Mon 5/11

5:10 am-11:46 am

1 stop5h 36m

$386

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 7/4

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Sat 7/11

9:20 am-5:35 pm

1 stop7h 15m

$391

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 7/10

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Sat 7/18

9:20 am-5:35 pm

1 stop7h 15m

$392

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 5/7

10:35 am-3:14 pm

1 stop5h 39m

Winnipeg

Mon 5/11

8:10 am-9:27 pm

2 stops12h 17m

$395

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 5/25

6:30 pm-11:10 am

1 stop17h 40m

Winnipeg

Wed 6/3

7:00 am-5:40 pm

1 stop9h 40m

$398

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/27

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Wed 6/3

9:20 am-5:35 pm

1 stop7h 15m

$402

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 4/30

5:30 am-10:09 am

1 stop5h 39m

Winnipeg

Sat 5/9

11:00 am-6:07 pm

1 stop6h 07m

$403

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/27

7:10 am-5:58 pm

2 stops11h 48m

Winnipeg

Wed 6/3

9:20 am-5:35 pm

1 stop7h 15m

$404

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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, 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 August is your next best option. Flight prices from Boston to Winnipeg during August average around $420.

How have Boston to Winnipeg flight prices changed over time?

As of April 2026, prices for Boston to Winnipeg flights are approximately 39% 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 14m
Direct flights	None

The fastest flight from Boston to Winnipeg takes 6h 14m

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 6h 14m, 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 April 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 (63% of total bookings). The next most popular airlines are Delta (21%) and United Airlines (16%).

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 $131	Free Cancellation	Rating 7.9 8,409 reviews	Search Delta flights
United Airlines	PriceFrom $149	Free Cancellation	Rating 7.4 9,579 reviews	Search United Airlines flights
Air Canada	PriceFrom $194	Free Cancellation	Rating 7.1 10,917 reviews	Search Air Canada 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.