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?

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

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 12m.

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

Delta, Porter Airlines, and WestJet are the most popular carriers operating from Boston Logan Intl to Winnipeg

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

Montreal (YUL) was the most common stop: 57% 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 May 2026, 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.

$198 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 $585 to $374. The lowest price recently found on this route was $397.

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

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

11:40 am - 7:05 pm

YWG

BOS

6h 25m

1 stop

$397Porter Airlines

Tue, Jun 16 - Tue, Jun 23

11:15 am - 7:49 pm

BOS

YWG

9h 34m

1 stop

11:40 am - 7:05 pm

YWG

BOS

6h 25m

1 stop

$405Porter Airlines

Tue, Jun 16 - Wed, Jun 17

11:15 am - 9:45 am

BOS

YWG

23h 30m

1 stop

6:15 am - 4:46 pm

YWG

BOS

9h 31m

1 stop

$411Multiple Airlines

Tue, Jun 16 - Thu, Jun 18

3:25 pm - 9:45 am

BOS

YWG

19h 20m

2 stops

9:20 am - 7:05 pm

YWG

BOS

8h 45m

2 stops

$423Multiple Airlines

Tue, Jun 16 - Tue, Jun 23

10:05 am - 7:49 pm

BOS

YWG

10h 44m

1 stop

6:05 pm - 8:55 pm

YWG

BOS

25h 50m

2 stops

$432Multiple Airlines

Tue, Jun 16 - Thu, Jun 18

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

4:25 pm - 8:55 pm

YWG

BOS

27h 30m

2 stops

$433Multiple Airlines

Tue, Jun 16 - Wed, Jun 17

7:25 am - 11:40 pm

BOS

YWG

17h 15m

1 stop

6:00 am - 5:40 pm

YWG

BOS

10h 40m

1 stop

$435WestJet

Sun, Sep 6 - Sat, Sep 12

10:40 am - 3:09 pm

BOS

YWG

5h 29m

1 stop

8:10 am - 2:41 pm

YWG

BOS

5h 31m

1 stop

$446Air Canada

Tue, Sep 22 - Wed, Sep 23

7:15 pm - 8:40 am

BOS

YWG

14h 25m

1 stop

9:25 am - 7:15 pm

YWG

BOS

8h 50m

1 stop

$448Multiple Airlines

Sat, Jul 11 - Sat, Jul 18

10:05 am - 3:19 pm

BOS

YWG

6h 14m

1 stop

6:05 pm - 10:31 am

YWG

BOS

15h 26m

1 stop

$449Multiple Airlines

Wed, Jun 10 - Sun, Jun 14

Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets

Porter Airlines

Jun 16

BOS10:05 amBoston Logan Intl

6h 14m

1 stop

YWG3:19 pmWinnipeg

Jun 23

YWG11:40 amWinnipeg

6h 25m

1 stop

BOS7:05 pmBoston Logan Intl

$397

Porter Airlines

Jun 16

BOS11:15 amBoston Logan Intl

9h 34m

1 stop

YWG7:49 pmWinnipeg

Jun 17

YWG11:40 amWinnipeg

6h 25m

1 stop

BOS7:05 pmBoston Logan Intl

$405

Porter Airlines

Sep 4

BOS10:05 amBoston Logan Intl

8h 53m

2 stops

YWG5:58 pmWinnipeg

Sep 8

YWG9:20 amWinnipeg

10h 35m

2 stops

BOS8:55 pmBoston Logan Intl

$469

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets

Air Canada

Sep 22

BOS10:40 amBoston Logan Intl

5h 29m

1 stop

YWG3:09 pmWinnipeg

Sep 23

YWG8:10 amWinnipeg

5h 31m

1 stop

BOS2:41 pmBoston Logan Intl

$446

Air Canada

Jun 15

BOS10:45 amBoston Logan Intl

8h 28m

1 stop

YWG6:13 pmWinnipeg

Jun 17

YWG8:10 amWinnipeg

6h 58m

1 stop

BOS4:08 pmBoston Logan Intl

$451

Air Canada

Sep 22

BOS10:40 amBoston Logan Intl

5h 29m

1 stop

YWG3:09 pmWinnipeg

Sep 23

YWG12:20 pmWinnipeg

8h 07m

2 stops

BOS9:27 pmBoston Logan Intl

$460

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 6/16

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Tue 6/23

11:40 am-7:05 pm

1 stop6h 25m

$397

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 6/16

11:15 am-7:49 pm

1 stop9h 34m

Winnipeg

Wed 6/17

11:40 am-7:05 pm

1 stop6h 25m

$405

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 6/16

11:15 am-9:45 am

1 stop23h 30m

Winnipeg

Thu 6/18

6:15 am-4:46 pm

1 stop9h 31m

$411

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 6/16

3:25 pm-9:45 am

2 stops19h 20m

Winnipeg

Tue 6/23

9:20 am-7:05 pm

2 stops8h 45m

$423

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 6/16

10:05 am-7:49 pm

1 stop10h 44m

Winnipeg

Thu 6/18

6:05 pm-8:55 pm

2 stops25h 50m

$432

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 6/16

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Wed 6/17

4:25 pm-8:55 pm

2 stops27h 30m

$433

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 9/6

7:25 am-11:40 pm

1 stop17h 15m

Winnipeg

Sat 9/12

6:00 am-5:40 pm

1 stop10h 40m

$435

Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 9/22

10:40 am-3:09 pm

1 stop5h 29m

Winnipeg

Wed 9/23

8:10 am-2:41 pm

1 stop5h 31m

$446

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 7/11

7:15 pm-8:40 am

1 stop14h 25m

Winnipeg

Sat 7/18

9:25 am-7:15 pm

1 stop8h 50m

$448

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 6/10

10:05 am-3:19 pm

1 stop6h 14m

Winnipeg

Sun 6/14

6:05 pm-10:31 am

1 stop15h 26m

$449

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 typical price of a round-trip flight between Boston and Winnipeg?

What is the cheapest month to fly to Winnipeg?

In general, August 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 $420. If you’re not able to fly to Winnipeg in August, then September is your next best option. Flight prices from Boston to Winnipeg during September average around $438.

How far in advance should I book a flight from Boston 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 $542 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 $366 on momondo.

How have Boston to Winnipeg flight prices changed over time?

As of May 2026, prices for Boston to Winnipeg flights are approximately 151% 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 29m
Direct flights	None

The fastest flight from Boston to Winnipeg takes 5h 29m

There are no direct flights from Boston to Winnipeg. There are no popular flight routes from Boston to Winnipeg.

Search flight deals

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 5h 29m, 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 May 2026, 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 (14%), United Airlines (12%), and Porter Airlines (10%).

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
United Airlines	PriceFrom $149	Free Cancellation	Rating 7.4 9,750 reviews	Search United Airlines flights
Air Canada	PriceFrom $194	Free Cancellation	Rating 7.1 11,092 reviews	Search Air Canada flights
Delta	PriceFrom $228	Free Cancellation	Rating 7.9 8,426 reviews	Search Delta flights
Porter Airlines	PriceFrom $293	Free Cancellation	Rating 8.0 439 reviews	Search Porter Airlines 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.