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Cheap flights from Boston to Winnipeg from $107

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 1/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Boston to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
10:15 am - 4:35 pm
BOS
-
YWG
7h 20m
1 stop
Air Canada Logo
8:15 am - 2:52 pm
YWG
-
BOS
5h 37m
1 stop
$234Air Canada
Thu, Feb 26 - Thu, Mar 5
Air Canada Logo
5:30 am - 10:15 am
BOS
-
YWG
5h 45m
1 stop
Air Canada Logo
5:30 am - 2:52 pm
YWG
-
BOS
8h 22m
2 stops
$245Air Canada
Thu, Feb 26 - Thu, Mar 5
Air Canada Logo
6:15 am - 12:39 pm
BOS
-
YWG
7h 24m
1 stop
Air Canada Logo
8:15 am - 2:52 pm
YWG
-
BOS
5h 37m
1 stop
$255Air Canada
Wed, Feb 11 - Wed, Feb 18
Air Canada Logo
6:15 am - 12:39 pm
BOS
-
YWG
7h 24m
1 stop
Air Canada Logo
6:00 am - 2:52 pm
YWG
-
BOS
7h 52m
2 stops
$261Air Canada
Wed, Feb 11 - Wed, Feb 18
Air Canada Logo
3:40 pm - 9:19 pm
BOS
-
YWG
6h 39m
1 stop
Air Canada Logo
5:10 am - 11:46 am
YWG
-
BOS
5h 36m
1 stop
$274Air Canada
Fri, May 1 - Wed, May 6
Air Canada Logo
10:15 am - 4:35 pm
BOS
-
YWG
7h 20m
1 stop
Air Canada Logo
8:15 am - 2:52 pm
YWG
-
BOS
5h 37m
1 stop
$276Air Canada
Thu, Feb 26 - Tue, Mar 3
United Airlines Logo
9:30 am - 10:24 pm
BOS
-
YWG
13h 54m
1 stop
United Airlines Logo
7:00 am - 9:33 pm
YWG
-
BOS
13h 33m
1 stop
$278United Airlines
Tue, Jun 2 - Sat, Jun 6
Air Canada Logo
5:00 pm - 11:13 pm
BOS
-
YWG
7h 13m
1 stop
Air Canada Logo
8:15 am - 4:08 pm
YWG
-
BOS
6h 53m
1 stop
$279Air Canada
Wed, May 27 - Tue, Jun 2
Air Canada Logo
5:30 am - 10:15 am
BOS
-
YWG
5h 45m
1 stop
Air Canada Logo
6:00 am - 2:52 pm
YWG
-
BOS
7h 52m
2 stops
$281Air Canada
Mon, Mar 2 - Wed, Mar 4
United Airlines Logo
6:00 am - 11:57 am
BOS
-
YWG
6h 57m
1 stop
United Airlines Logo
2:20 pm - 9:28 pm
YWG
-
BOS
6h 08m
1 stop
$284United Airlines
Fri, Feb 27 - Fri, Mar 6

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets
Air Canada
Feb 26
BOS10:15 amBoston Logan Intl
7h 20m
1 stop
YWG4:35 pmWinnipeg
Mar 5
YWG8:15 amWinnipeg
5h 37m
1 stop
BOS2:52 pmBoston Logan Intl
$234
Air Canada
Feb 26
BOS5:30 amBoston Logan Intl
5h 45m
1 stop
YWG10:15 amWinnipeg
Mar 5
YWG5:30 amWinnipeg
8h 22m
2 stops
BOS2:52 pmBoston Logan Intl
$245
Air Canada
Feb 11
BOS6:15 amBoston Logan Intl
7h 24m
1 stop
YWG12:39 pmWinnipeg
Feb 18
YWG8:15 amWinnipeg
5h 37m
1 stop
BOS2:52 pmBoston Logan Intl
$255

United Airlines flights from Boston to Winnipeg

Our best United Airlines deals on Boston to Winnipeg flight tickets
United Airlines
Jun 2
BOS9:30 amBoston Logan Intl
13h 54m
1 stop
YWG10:24 pmWinnipeg
Jun 6
YWG7:00 amWinnipeg
13h 33m
1 stop
BOS9:33 pmBoston Logan Intl
$278
United Airlines
Feb 27
BOS6:00 amBoston Logan Intl
6h 57m
1 stop
YWG11:57 amWinnipeg
Mar 6
YWG2:20 pmWinnipeg
6h 08m
1 stop
BOS9:28 pmBoston Logan Intl
$284
United Airlines
May 27
BOS11:55 amBoston Logan Intl
9h 53m
1 stop
YWG8:48 pmWinnipeg
Jun 2
YWG7:00 amWinnipeg
15h 54m
2 stops
BOS11:54 pmBoston Logan Intl
$287

momondo Fare Finder

 
Customize your flight search to find flights from Boston to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated January 15, 2026.
Use the filters below to find and compare flights from Boston to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 2/26

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

Thu 3/5

8:15 am-2:52 pm

1 stop5h 37m

$234

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 2/26

5:30 am-10:15 am

1 stop5h 45m

Winnipeg

Thu 3/5

5:30 am-2:52 pm

2 stops8h 22m

$245

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 2/11

6:15 am-12:39 pm

1 stop7h 24m

Winnipeg

Wed 2/18

8:15 am-2:52 pm

1 stop5h 37m

$255

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 2/11

6:15 am-12:39 pm

1 stop7h 24m

Winnipeg

Wed 2/18

6:00 am-2:52 pm

2 stops7h 52m

$261

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 5/1

3:40 pm-9:19 pm

1 stop6h 39m

Winnipeg

Wed 5/6

5:10 am-11:46 am

1 stop5h 36m

$274

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 2/26

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

Tue 3/3

8:15 am-2:52 pm

1 stop5h 37m

$276

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 6/2

9:30 am-10:24 pm

1 stop13h 54m

Winnipeg

Sat 6/6

7:00 am-9:33 pm

1 stop13h 33m

$278

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 5/27

5:00 pm-11:13 pm

1 stop7h 13m

Winnipeg

Tue 6/2

8:15 am-4:08 pm

1 stop6h 53m

$279

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 3/2

5:30 am-10:15 am

1 stop5h 45m

Winnipeg

Wed 3/4

6:00 am-2:52 pm

2 stops7h 52m

$281

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 2/27

6:00 am-11:57 am

1 stop6h 57m

Winnipeg

Fri 3/6

2:20 pm-9:28 pm

1 stop6h 08m

$284

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

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 March is your next best option. Flight prices from Boston to Winnipeg during March average around $317.

How have Boston to Winnipeg flight prices changed over time?

As of January 2026, prices for Boston to Winnipeg flights are approximately 43% 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 46m

Direct flights

None
The fastest flight from Boston to Winnipeg takes 5h 46m
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 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?

  • 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?

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
DeltaPriceFrom $131Free CancellationRating
7.9
8,049 reviews
Search Delta flights
Air CanadaPriceFrom $134Free CancellationRating
7.1
10,623 reviews
Search Air Canada flights
United AirlinesPriceFrom $172Free CancellationRating
7.4
9,164 reviews
Search United Airlines flights

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
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.

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.
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