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

Air Canada is the most popular carrier operating from Boston Logan Intl to Winnipeg

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.

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 January 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.

$84 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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5:30 am - 10:15 am

BOS

YWG

5h 45m1 stop

8:15 am - 2:52 pm

YWG

BOS

5h 37m1 stop

$399Air Canada

Sun, Feb 15 - Fri, Feb 20

5:30 am - 10:15 am

BOS

YWG

5h 45m1 stop

1:30 pm - 10:37 pm

YWG

BOS

8h 07m1 stop

$402Air Canada

Tue, Feb 10 - Tue, Feb 10

3:50 pm - 10:46 pm

BOS

YWG

7h 56m1 stop

11:45 am - 5:58 pm

YWG

BOS

5h 13m1 stop

$409Porter Airlines

Sun, May 24 - Sun, May 31

3:50 pm - 10:46 pm

BOS

YWG

7h 56m1 stop

11:45 am - 9:31 pm

YWG

BOS

8h 46m2 stops

$413Porter Airlines

Sun, May 24 - Sun, May 31

12:15 pm - 10:46 pm

BOS

YWG

11h 31m2 stops

11:45 am - 9:31 pm

YWG

BOS

8h 46m2 stops

$421Porter Airlines

Sun, May 24 - Sun, May 31

3:30 pm - 11:32 am

BOS

YWG

21h 02m2 stops

8:20 pm - 11:05 am

YWG

BOS

13h 45m1 stop

$451Multiple Airlines

Mon, Feb 16 - Sat, Feb 21

7:05 am - 11:47 pm

BOS

YWG

17h 42m2 stops

8:20 pm - 11:05 am

YWG

BOS

13h 45m1 stop

$483Multiple Airlines

Sun, Feb 15 - Fri, Feb 20

5:30 am - 10:16 am

BOS

YWG

5h 46m1 stop

8:15 am - 2:52 pm

YWG

BOS

5h 37m1 stop

$500Air Canada

Thu, Jan 22 - Mon, Jan 26

10:15 am - 8:28 pm

BOS

YWG

11h 13m2 stops

8:15 am - 2:52 pm

YWG

BOS

5h 37m1 stop

$505Air Canada

Thu, Jan 22 - Mon, Jan 26

10:15 am - 4:35 pm

BOS

YWG

7h 20m1 stop

5:30 am - 2:52 pm

YWG

BOS

8h 22m2 stops

$512Air Canada

Thu, Jan 22 - Mon, Jan 26

Delta flights from Boston to Winnipeg

Our best Delta deals on Boston to Winnipeg flight tickets

Delta

Jun 14

BOS7:10 amBoston Logan Intl

10h 44m

1 stop

YWG4:54 pmWinnipeg

Jun 20

YWG12:40 pmWinnipeg

8h 40m

1 stop

BOS10:20 pmBoston Logan Intl

$615

Find similar

Delta

Jun 26

BOS7:10 amBoston Logan Intl

10h 44m

1 stop

YWG4:54 pmWinnipeg

Jul 5

YWG12:40 pmWinnipeg

10h 12m

1 stop

BOS11:52 pmBoston Logan Intl

$669

Find similar

Delta

May 24

BOS5:40 amBoston Logan Intl

6h 54m

1 stop

YWG11:34 amWinnipeg

May 31

YWG12:40 pmWinnipeg

10h 12m

1 stop

BOS11:52 pmBoston Logan Intl

$691

Find similar

WestJet flights from Boston to Winnipeg

Our best WestJet deals on Boston to Winnipeg flight tickets

WestJet

Jun 14

BOS5:30 amBoston Logan Intl

18h 30m

2 stops

YWG11:00 pmWinnipeg

Jun 20

YWG6:30 amWinnipeg

16h 02m

2 stops

BOS11:32 pmBoston Logan Intl

$735

Find similar

WestJet

Jun 26

BOS5:30 amBoston Logan Intl

18h 30m

2 stops

YWG11:00 pmWinnipeg

Jul 5

YWG6:15 pmWinnipeg

25h 16m

2 stops

BOS8:31 pmBoston Logan Intl

$737

Find similar

WestJet

Jun 26

BOS8:15 amBoston Logan Intl

16h 12m

1 stop

YWG11:27 pmWinnipeg

Jul 5

YWG6:15 pmWinnipeg

25h 16m

2 stops

BOS8:31 pmBoston Logan Intl

$741

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 2/15

5:30 am-10:15 am

1 stop5h 45m

Winnipeg

Fri 2/20

8:15 am-2:52 pm

1 stop5h 37m

$399

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 2/10

5:30 am-10:15 am

1 stop5h 45m

Winnipeg

Tue 2/10

1:30 pm-10:37 pm

1 stop8h 07m

$402

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 5/24

3:50 pm-10:46 pm

1 stop7h 56m

Winnipeg

Sun 5/31

11:45 am-5:58 pm

1 stop5h 13m

$409

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 5/24

3:50 pm-10:46 pm

1 stop7h 56m

Winnipeg

Sun 5/31

11:45 am-9:31 pm

2 stops8h 46m

$413

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 5/24

12:15 pm-10:46 pm

2 stops11h 31m

Winnipeg

Sun 5/31

11:45 am-9:31 pm

2 stops8h 46m

$421

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 2/16

3:30 pm-11:32 am

2 stops21h 02m

Winnipeg

Sat 2/21

8:20 pm-11:05 am

1 stop13h 45m

$451

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 2/15

7:05 am-11:47 pm

2 stops17h 42m

Winnipeg

Fri 2/20

8:20 pm-11:05 am

1 stop13h 45m

$483

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/22

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

Mon 1/26

8:15 am-2:52 pm

1 stop5h 37m

$500

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/22

10:15 am-8:28 pm

2 stops11h 13m

Winnipeg

Mon 1/26

8:15 am-2:52 pm

1 stop5h 37m

$505

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/22

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

Mon 1/26

5:30 am-2:52 pm

2 stops8h 22m

$512

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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.

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 $465 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 January 2026, prices for Boston to Winnipeg flights are approximately 20% 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 45m
Direct flights	None

The fastest flight from Boston to Winnipeg takes 5h 45m

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 45m, 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 January 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 (68% of total bookings). The next most popular airlines are Delta (17%) and United Airlines (15%).

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 10,571 reviews	Search Air Canada flights
Delta	PriceFrom $143	Free Cancellation	Rating 7.9 8,011 reviews	Search Delta flights
United Airlines	PriceFrom $172	Free Cancellation	Rating 7.4 9,125 reviews	Search United Airlines flights

Scanterbury

Portage la Prairie

Selkirk

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.