Which airport is the most popular layover for flights between Boston and Winnipeg?

Montreal (YUL) was the most common stop: 60% of momondo users choosing 1-stop flights on this route connected there.

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 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 connection time from Boston to Winnipeg?

Toronto (YYZ) has the shortest average layover time for this route: 1h 17m.

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 travel time from Boston to Winnipeg?

Flights connecting via Toronto (YYZ) have the shortest average one-way travel time: 6h 08m.

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

Porter Airlines, Air Canada, and United Airlines 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 August 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.

$196 Cheap Flights from Boston to Winnipeg (BOS-YWG) in 2025

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Boston to Winnipeg (BOS-YWG)

Round-trip

One-way

Last minute

Cheap round-trip flights

5:50 am - 11:10 pmBOS-YWG

18h 20m2 stops

9:15 pm - 6:10 pmYWG-BOS

19h 55m1 stop

$327

Find Deal

Sat, Sep 20 - Sat, Oct 11

6:00 am - 1:56 pmBOS-YWG

8h 56m2 stops

5:00 am - 11:29 amYWG-BOS

5h 29m1 stop

$333Air Canada

Find Deal

Thu, Sep 18 - Wed, Sep 24

6:49 pm - 4:22 pmBOS-YWG

22h 33m2 stops

12:30 pm - 9:30 amYWG-BOS

20h 00m2 stops

$339

Find Deal

Thu, Sep 18 - Wed, Sep 24

6:00 am - 9:01 amBOS-YWG

28h 01m3 stops

3:15 pm - 9:30 amYWG-BOS

17h 15m2 stops

$344

Find Deal

Thu, Sep 18 - Wed, Sep 24

7:00 pm - 7:23 pmBOS-YWG

25h 23m1 stop

8:15 pm - 6:10 pmYWG-BOS

20h 55m1 stop

$361WestJet

Find Deal

Sun, Sep 14 - Sun, Sep 21

7:00 pm - 7:23 pmBOS-YWG

25h 23m1 stop

5:30 pm - 6:10 pmYWG-BOS

23h 40m2 stops

$397WestJet

Find Deal

Sun, Sep 14 - Sun, Sep 21

3:30 pm - 10:25 amBOS-YWG

19h 55m1 stop

11:20 am - 6:28 pmYWG-BOS

6h 08m1 stop

$441Porter Airlines

Find Deal

Fri, Oct 10 - Tue, Oct 14

6:00 am - 3:31 pmBOS-YWG

10h 31m2 stops

2:20 pm - 11:57 pmYWG-BOS

8h 37m2 stops

$455United Airlines

Find Deal

Thu, Sep 18 - Mon, Sep 22

6:00 am - 11:57 amBOS-YWG

6h 57m1 stop

2:20 pm - 9:49 pmYWG-BOS

6h 29m1 stop

$517United Airlines

Find Deal

Wed, Jan 14 - Wed, Jan 21

3:30 pm - 11:13 amBOS-YWG

20h 43m1 stop

4:25 pm - 6:10 pmYWG-BOS

24h 45m1 stop

$562Porter Airlines

Find Deal

Wed, Nov 26 - Sun, Nov 30

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets

Air Canada

Sep 18

BOS6:00 amBoston Logan Intl

8h 56m

2 stops

YWG1:56 pmWinnipeg

Sep 24

YWG5:00 amWinnipeg

5h 29m

1 stop

BOS11:29 amBoston Logan Intl

$333

Find similar

Air Canada

Sep 25

BOS6:00 amBoston Logan Intl

10h 31m

2 stops

YWG3:31 pmWinnipeg

Oct 1

YWG7:55 amWinnipeg

5h 35m

1 stop

BOS2:30 pmBoston Logan Intl

$373

Find similar

Air Canada

Sep 25

BOS8:00 amBoston Logan Intl

8h 31m

2 stops

YWG3:31 pmWinnipeg

Oct 1

YWG5:00 amWinnipeg

11h 55m

2 stops

BOS5:55 pmBoston Logan Intl

$380

Find similar

Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets

Porter Airlines

Oct 10

BOS3:30 pmBoston Logan Intl

19h 55m

1 stop

YWG10:25 amWinnipeg

Oct 14

YWG11:20 amWinnipeg

6h 08m

1 stop

BOS6:28 pmBoston Logan Intl

$441

Find similar

Porter Airlines

Nov 26

BOS3:30 pmBoston Logan Intl

20h 43m

1 stop

YWG11:13 amWinnipeg

Nov 30

YWG4:25 pmWinnipeg

24h 45m

1 stop

BOS6:10 pmBoston Logan Intl

$562

Find similar

Porter Airlines

Nov 26

BOS1:25 pmBoston Logan Intl

22h 48m

2 stops

YWG11:13 amWinnipeg

Nov 30

YWG4:25 pmWinnipeg

16h 10m

2 stops

BOS9:35 amBoston Logan Intl

$672

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 9/20

5:50 am-11:10 pm

2 stops18h 20m

Winnipeg

Sat 10/11

9:15 pm-6:10 pm

1 stop19h 55m

$327

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/18

6:00 am-1:56 pm

2 stops8h 56m

Winnipeg

Wed 9/24

5:00 am-11:29 am

1 stop5h 29m

$333

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/18

6:49 pm-4:22 pm

2 stops22h 33m

Winnipeg

Wed 9/24

12:30 pm-9:30 am

2 stops20h 00m

$339

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/18

6:00 am-9:01 am

3 stops28h 01m

Winnipeg

Wed 9/24

3:15 pm-9:30 am

2 stops17h 15m

$344

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 9/14

7:00 pm-7:23 pm

1 stop25h 23m

Winnipeg

Sun 9/21

8:15 pm-6:10 pm

1 stop20h 55m

$361

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 9/14

7:00 pm-7:23 pm

1 stop25h 23m

Winnipeg

Sun 9/21

5:30 pm-6:10 pm

2 stops23h 40m

$397

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 10/10

3:30 pm-10:25 am

1 stop19h 55m

Winnipeg

Tue 10/14

11:20 am-6:28 pm

1 stop6h 08m

$441

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/18

6:00 am-3:31 pm

2 stops10h 31m

Winnipeg

Mon 9/22

2:20 pm-11:57 pm

2 stops8h 37m

$455

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 1/14

6:00 am-11:57 am

1 stop6h 57m

Winnipeg

Wed 1/21

2:20 pm-9:49 pm

1 stop6h 29m

$517

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 11/26

3:30 pm-11:13 am

1 stop20h 43m

Winnipeg

Sun 11/30

4:25 pm-6:10 pm

1 stop24h 45m

$562

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 May is your next best option. Flight prices from Boston to Winnipeg during May average around $328.

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 $444 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 $336 on momondo.

How have Boston to Winnipeg flight prices changed over time?

As of August 2025, prices for Boston to Winnipeg flights are approximately 19% 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

Direct flights	None

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 40m, 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 August 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 (64% of total bookings). The next most popular airlines are Delta (17%), United Airlines (11%), and Porter Airlines (9%).

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 10,000 reviews	Search Air Canada flights
United Airlines	PriceFrom $172	Free Cancellation	Rating 7.4 8,943 reviews	Search United Airlines flights
Delta	PriceFrom $274	Free Cancellation	Rating 7.9 7,979 reviews	Search Delta flights
Porter Airlines	PriceFrom $283	Free Cancellation	Rating 7.9 346 reviews	Search Porter Airlines flights

Scanterbury

Selkirk

Morden

Portage la Prairie

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.

An easier way to manage your Winnipeg trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Sun 8/31

Sun 9/7

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada

Airports servicing Manitoba

Lac Brochet Airport

South Indian Lake Airport

Brandon Airport

Brochet Airport

Berens River Airport

Cross Island Cross Lake Airport

Popular cities in Canada

Flights to Torontofrom $88

Flights to Vancouverfrom $74

Flights to Montrealfrom $170

Flights to Calgaryfrom $142

Flights to Ottawafrom $215

Flights to Halifaxfrom $134

Flights to Québec Cityfrom $143

Flights to Saskatoonfrom $123

Flights to Kelownafrom $180

Flights to St. John'sfrom $289

Flights to Reginafrom $211

Flights to Monctonfrom $364

Cheap flights from Boston to Winnipeg from $234

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Winnipeg departing on 11/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Boston to Winnipeg (BOS-YWG)

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets

Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Boston to Winnipeg that are best for you.

See travel insights to Winnipeg from

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

What is the cheapest month to fly to Winnipeg?

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

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

How far in advance should I book a flight to Winnipeg?

How have Boston to Winnipeg flight prices changed over time?

As of August 2025, prices for Boston to Winnipeg flights are approximately 19% cheaper when compared to flights at the same time last year.

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

Porter Airlines, Air Canada, and United Airlines are the most popular carriers operating from Boston Logan Intl to Winnipeg

What airlines fly to Winnipeg?

Which airport is the most popular layover for flights between Boston and Winnipeg?

Montreal (YUL) was the most common stop: 60% 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.

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 08m.

Which layover airport has the shortest connection time from Boston to Winnipeg?

Toronto (YYZ) has the shortest average layover time for this route: 1h 17m.

When to book flights from Boston to Winnipeg

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

Direct flights

How far is Boston Logan Intl to Winnipeg by plane?

When did momondo last update prices for flights from Boston Logan Intl Airport to Winnipeg Airport?

How many operators does momondo search 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?

What documentation or ID do you need to fly to Winnipeg Airport?

What is the most popular airline from Boston to Winnipeg?

Best airlines flying from Boston to Winnipeg

Compare and see reviews for airlines that fly from Boston to Winnipeg with momondo

Traveling to a place near Winnipeg?

Why use momondo?

Why should I use momondo to find a flight deal from Boston to Winnipeg?

Can I find flights from Boston to Winnipeg with flexible booking policies on momondo?

How can momondo help me find flights from Boston to Winnipeg?

I’m not ready to book a flight from Boston to Winnipeg right now. Can momondo alert me if prices change?

An easier way to manage your Winnipeg trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Canada

Airports servicing Manitoba