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 63% 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 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.

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 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 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.

$109 Cheap Flights from Boston to Winnipeg in 2025/26

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Find the cheapest flights from Boston to Winnipeg

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6:00 am - 3:09 pmBOS-YWG

10h 09m1 stop

7:30 am - 9:57 amYWG-BOS

25h 27m1 stop

$271Multiple Airlines

Find Deal

Wed, Mar 18 - Fri, Mar 20

6:00 am - 3:09 pmBOS-YWG

10h 09m1 stop

5:00 am - 6:10 pmYWG-BOS

12h 10m2 stops

$318Multiple Airlines

Find Deal

Wed, Mar 18 - Fri, Mar 20

6:00 am - 3:09 pmBOS-YWG

10h 09m1 stop

8:00 am - 11:57 pmYWG-BOS

14h 57m1 stop

$351Multiple Airlines

Find Deal

Fri, Mar 6 - Mon, Mar 9

6:00 am - 3:09 pmBOS-YWG

10h 09m1 stop

4:25 pm - 11:05 amYWG-BOS

17h 40m2 stops

$358Multiple Airlines

Find Deal

Fri, Mar 6 - Mon, Mar 9

3:30 pm - 11:13 amBOS-YWG

20h 43m1 stop

9:00 pm - 12:05 amYWG-BOS

26h 05m2 stops

$375Multiple Airlines

Find Deal

Mon, Feb 2 - Tue, Feb 17

5:40 am - 11:32 amBOS-YWG

30h 52m2 stops

8:00 am - 12:07 amYWG-BOS

15h 07m1 stop

$441Multiple Airlines

Find Deal

Sat, Apr 11 - Mon, Apr 13

5:27 pm - 12:40 amBOS-YWG

32h 13m3 stops

5:00 am - 11:57 pmYWG-BOS

17h 57m2 stops

$448Multiple Airlines

Find Deal

Mon, Feb 2 - Tue, Feb 17

5:40 am - 11:13 amBOS-YWG

30h 33m3 stops

8:00 am - 12:07 amYWG-BOS

15h 07m1 stop

$456Multiple Airlines

Find Deal

Sat, Apr 11 - Mon, Apr 13

5:30 am - 10:16 amBOS-YWG

5h 46m1 stop

5:30 am - 12:12 pmYWG-BOS

5h 42m1 stop

$460Air Canada

Find Deal

Thu, Jan 8 - Mon, Jan 12

10:15 am - 4:35 pmBOS-YWG

7h 20m1 stop

5:30 am - 2:52 pmYWG-BOS

8h 22m2 stops

$465Air Canada

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Thu, Jan 8 - Mon, Jan 12

Delta flights from Boston to Winnipeg

Our best Delta deals on Boston to Winnipeg flight tickets

Delta

Jan 12

BOS5:50 amBoston Logan Intl

6h 13m

1 stop

YWG11:03 amWinnipeg

Jan 13

YWG5:21 pmWinnipeg

5h 31m

1 stop

BOS11:52 pmBoston Logan Intl

$474

Find similar

Delta

Jan 12

BOS5:50 amBoston Logan Intl

6h 13m

1 stop

YWG11:03 amWinnipeg

Jan 13

YWG5:21 pmWinnipeg

18h 02m

2 stops

BOS12:23 pmBoston Logan Intl

$555

Find similar

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets

Air Canada

Jan 8

BOS5:30 amBoston Logan Intl

5h 46m

1 stop

YWG10:16 amWinnipeg

Jan 12

YWG5:30 amWinnipeg

5h 42m

1 stop

BOS12:12 pmBoston Logan Intl

$460

Find similar

Air Canada

Jan 8

BOS10:15 amBoston Logan Intl

7h 20m

1 stop

YWG4:35 pmWinnipeg

Jan 12

YWG5:30 amWinnipeg

8h 22m

2 stops

BOS2:52 pmBoston Logan Intl

$465

Find similar

Air Canada

Jan 8

BOS10:15 amBoston Logan Intl

11h 13m

2 stops

YWG8:28 pmWinnipeg

Jan 12

YWG5:30 amWinnipeg

8h 22m

2 stops

BOS2:52 pmBoston Logan Intl

$470

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 3/18

6:00 am-3:09 pm

1 stop10h 09m

Winnipeg

Fri 3/20

7:30 am-9:57 am

1 stop25h 27m

$271

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 3/18

6:00 am-3:09 pm

1 stop10h 09m

Winnipeg

Fri 3/20

5:00 am-6:10 pm

2 stops12h 10m

$318

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 3/6

6:00 am-3:09 pm

1 stop10h 09m

Winnipeg

Mon 3/9

8:00 am-11:57 pm

1 stop14h 57m

$351

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 3/6

6:00 am-3:09 pm

1 stop10h 09m

Winnipeg

Mon 3/9

4:25 pm-11:05 am

2 stops17h 40m

$358

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 2/2

3:30 pm-11:13 am

1 stop20h 43m

Winnipeg

Tue 2/17

9:00 pm-12:05 am

2 stops26h 05m

$375

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 4/11

5:40 am-11:32 am

2 stops30h 52m

Winnipeg

Mon 4/13

8:00 am-12:07 am

1 stop15h 07m

$441

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 2/2

5:27 pm-12:40 am

3 stops32h 13m

Winnipeg

Tue 2/17

5:00 am-11:57 pm

2 stops17h 57m

$448

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 4/11

5:40 am-11:13 am

3 stops30h 33m

Winnipeg

Mon 4/13

8:00 am-12:07 am

1 stop15h 07m

$456

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/8

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

Mon 1/12

5:30 am-12:12 pm

1 stop5h 42m

$460

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/8

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

Mon 1/12

5:30 am-2:52 pm

2 stops8h 22m

$465

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 January is your next best option. Flight prices from Boston to Winnipeg during January average around $341.

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 $446 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 0% 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.

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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 46m, 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 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 (63% of total bookings). The next most popular airlines are Delta (17%), United Airlines (13%), and Porter Airlines (7%).

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 10,498 reviews	Search Air Canada flights
United Airlines	PriceFrom $172	Free Cancellation	Rating 7.4 9,065 reviews	Search United Airlines flights
Delta	PriceFrom $228	Free Cancellation	Rating 7.9 8,011 reviews	Search Delta flights
Porter Airlines	PriceFrom $388	Free Cancellation	Rating 8.0 394 reviews	Search Porter Airlines 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.