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Cheap flights from Boston to Winnipeg from $186

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 2/23. 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.
Multiple Airlines Logo
12:35 pm - 3:09 pm
BOS
-
YWG
27h 34m1 stop
Multiple Airlines Logo
7:30 am - 1:04 am
YWG
-
BOS
16h 34m1 stop
$244Multiple Airlines
Tue, Mar 31 - Sun, Apr 5
United Airlines Logo
6:00 am - 11:57 am
BOS
-
YWG
6h 57m1 stop
United Airlines Logo
2:00 pm - 12:59 am
YWG
-
BOS
9h 59m1 stop
$284United Airlines
Fri, Mar 27 - Mon, Mar 30
Air Canada Logo
5:30 am - 10:16 am
BOS
-
YWG
5h 46m1 stop
Air Canada Logo
5:30 am - 12:12 pm
YWG
-
BOS
5h 42m1 stop
$290Air Canada
Thu, Jan 22 - Mon, Jan 26
Delta Logo
5:50 am - 12:00 pm
BOS
-
YWG
7h 10m1 stop
Delta Logo
12:50 pm - 11:49 pm
YWG
-
BOS
9h 59m1 stop
$294Delta
Fri, Mar 27 - Mon, Mar 30
Air Canada Logo
5:30 am - 10:16 am
BOS
-
YWG
5h 46m1 stop
Air Canada Logo
5:30 am - 2:52 pm
YWG
-
BOS
8h 22m2 stops
$299Air Canada
Thu, Jan 22 - Mon, Jan 26
Air Canada Logo
5:30 am - 10:16 am
BOS
-
YWG
5h 46m1 stop
Air Canada Logo
7:05 pm - 12:12 pm
YWG
-
BOS
16h 07m1 stop
$315Air Canada
Thu, Jan 22 - Mon, Jan 26
Air Canada Logo
5:30 am - 10:15 am
BOS
-
YWG
5h 45m1 stop
Air Canada Logo
5:30 pm - 10:02 am
YWG
-
BOS
15h 32m1 stop
$316Air Canada
Fri, Feb 20 - Fri, Feb 27
Multiple Airlines Logo
3:30 pm - 11:32 am
BOS
-
YWG
21h 02m2 stops
Multiple Airlines Logo
7:30 am - 1:13 am
YWG
-
BOS
16h 43m1 stop
$327Multiple Airlines
Fri, Feb 20 - Fri, Feb 27
Multiple Airlines Logo
3:30 pm - 11:35 pm
BOS
-
YWG
9h 05m2 stops
Multiple Airlines Logo
7:30 am - 1:04 am
YWG
-
BOS
16h 34m1 stop
$360Multiple Airlines
Tue, Mar 31 - Sun, Apr 5
Multiple Airlines Logo
5:34 am - 6:03 pm
BOS
-
YWG
13h 29m1 stop
Multiple Airlines Logo
9:00 pm - 1:13 am
YWG
-
BOS
27h 13m2 stops
$377Multiple Airlines
Mon, Jan 19 - Sat, Jan 24

American Airlines flights from Boston to Winnipeg

Our best American Airlines deals on Boston to Winnipeg flight tickets
American Airlines
Feb 20
BOS7:00 amBoston Logan Intl
17h 35m
3 stops
YWG11:35 pmWinnipeg
Feb 27
YWG12:10 pmWinnipeg
23h 19m
2 stops
BOS12:29 pmBoston Logan Intl
$773
American Airlines
Mar 31
BOS9:15 amBoston Logan Intl
15h 20m
3 stops
YWG11:35 pmWinnipeg
Apr 5
YWG12:10 pmWinnipeg
10h 13m
2 stops
BOS11:23 pmBoston Logan Intl
$810
American Airlines
Mar 27
BOS11:00 amBoston Logan Intl
13h 35m
2 stops
YWG11:35 pmWinnipeg
Mar 30
YWG6:00 amWinnipeg
12h 02m
3 stops
BOS7:02 pmBoston Logan Intl
$843

United Airlines flights from Boston to Winnipeg

Our best United Airlines deals on Boston to Winnipeg flight tickets
United Airlines
Mar 27
BOS6:00 amBoston Logan Intl
6h 57m
1 stop
YWG11:57 amWinnipeg
Mar 30
YWG2:00 pmWinnipeg
9h 59m
1 stop
BOS12:59 amBoston Logan Intl
$284
United Airlines
Jan 22
BOS1:30 pmBoston Logan Intl
11h 24m
2 stops
YWG11:54 pmWinnipeg
Jan 26
YWG5:30 amWinnipeg
12h 02m
2 stops
BOS6:32 pmBoston Logan Intl
$406
United Airlines
Feb 20
BOS1:55 pmBoston Logan Intl
10h 59m
2 stops
YWG11:54 pmWinnipeg
Feb 27
YWG2:20 pmWinnipeg
8h 37m
2 stops
BOS11:57 pmBoston Logan Intl
$572

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 8, 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

Tue 3/31

12:35 pm-3:09 pm

1 stop27h 34m

Winnipeg

Sun 4/5

7:30 am-1:04 am

1 stop16h 34m

$244

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 3/27

6:00 am-11:57 am

1 stop6h 57m

Winnipeg

Mon 3/30

2:00 pm-12:59 am

1 stop9h 59m

$284

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/22

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

Mon 1/26

5:30 am-12:12 pm

1 stop5h 42m

$290

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 3/27

5:50 am-12:00 pm

1 stop7h 10m

Winnipeg

Mon 3/30

12:50 pm-11:49 pm

1 stop9h 59m

$294

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/22

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

Mon 1/26

5:30 am-2:52 pm

2 stops8h 22m

$299

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/22

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

Mon 1/26

7:05 pm-12:12 pm

1 stop16h 07m

$315

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 2/20

5:30 am-10:15 am

1 stop5h 45m

Winnipeg

Fri 2/27

5:30 pm-10:02 am

1 stop15h 32m

$316

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 2/20

3:30 pm-11:32 am

2 stops21h 02m

Winnipeg

Fri 2/27

7:30 am-1:13 am

1 stop16h 43m

$327

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 3/31

3:30 pm-11:35 pm

2 stops9h 05m

Winnipeg

Sun 4/5

7:30 am-1:04 am

1 stop16h 34m

$360

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 1/19

5:34 am-6:03 pm

1 stop13h 29m

Winnipeg

Sat 1/24

9:00 pm-1:13 am

2 stops27h 13m

$377

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
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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

6h 11m

Direct flights

None
The fastest flight from Boston to Winnipeg takes 6h 11m
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 6h 11m, 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
Air CanadaPriceFrom $134Free CancellationRating
7.1
10,603 reviews
Search Air Canada flights
DeltaPriceFrom $143Free CancellationRating
7.9
8,029 reviews
Search Delta flights
United AirlinesPriceFrom $172Free CancellationRating
7.4
9,141 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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