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Cheap flights from Boston to Winnipeg from $366

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Winnipeg departing on 3/6. 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
9:00 am - 7:35 pm
BOS
-
YWG
11h 35m
1 stop
Multiple Airlines Logo
8:00 am - 5:15 pm
YWG
-
BOS
32h 15m
1 stop
$366Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 12:36 am
BOS
-
YWG
19h 36m
2 stops
Multiple Airlines Logo
8:00 am - 5:15 pm
YWG
-
BOS
32h 15m
1 stop
$367Multiple Airlines
Mon, Mar 2 - Mon, Mar 9
Multiple Airlines Logo
6:35 pm - 9:45 am
BOS
-
YWG
16h 10m
1 stop
Multiple Airlines Logo
6:00 am - 3:50 pm
YWG
-
BOS
8h 50m
1 stop
$368Multiple Airlines
Thu, May 14 - Mon, May 18
Multiple Airlines Logo
6:00 am - 3:09 pm
BOS
-
YWG
10h 09m
1 stop
Multiple Airlines Logo
8:00 am - 5:15 pm
YWG
-
BOS
32h 15m
1 stop
$375Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
6:10 pm - 3:09 pm
BOS
-
YWG
21h 59m
2 stops
Multiple Airlines Logo
8:00 am - 4:45 pm
YWG
-
BOS
31h 45m
3 stops
$381Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
6:10 pm - 3:09 pm
BOS
-
YWG
21h 59m
2 stops
Multiple Airlines Logo
8:00 am - 11:44 pm
YWG
-
BOS
14h 44m
1 stop
$382Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
6:10 pm - 3:09 pm
BOS
-
YWG
21h 59m
2 stops
Multiple Airlines Logo
12:20 pm - 11:44 pm
YWG
-
BOS
34h 24m
2 stops
$385Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
5:27 am - 6:03 pm
BOS
-
YWG
13h 36m
1 stop
Multiple Airlines Logo
8:00 am - 5:15 pm
YWG
-
BOS
32h 15m
1 stop
$389Multiple Airlines
Mon, Mar 2 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 12:40 am
BOS
-
YWG
19h 40m
2 stops
Multiple Airlines Logo
8:20 pm - 11:05 am
YWG
-
BOS
13h 45m
1 stop
$397Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
7:15 am - 5:15 pm
BOS
-
YWG
11h 00m
1 stop
Multiple Airlines Logo
9:05 pm - 12:05 pm
YWG
-
BOS
14h 00m
2 stops
$399Multiple Airlines
Thu, May 14 - Mon, May 18

United Airlines flights from Boston to Winnipeg

Our best United Airlines deals on Boston to Winnipeg flight tickets
United Airlines
Mar 2
BOS6:27 pmBoston Logan Intl
18h 30m
2 stops
YWG11:57 amWinnipeg
Mar 9
YWG5:30 amWinnipeg
8h 46m
2 stops
BOS3:16 pmBoston Logan Intl
$431
United Airlines
Mar 2
BOS7:05 amBoston Logan Intl
13h 29m
2 stops
YWG7:34 pmWinnipeg
Mar 4
YWG7:00 amWinnipeg
7h 55m
1 stop
BOS3:55 pmBoston Logan Intl
$445
United Airlines
Mar 2
BOS5:35 amBoston Logan Intl
12h 44m
2 stops
YWG5:19 pmWinnipeg
Mar 4
YWG5:30 amWinnipeg
8h 42m
2 stops
BOS3:12 pmBoston Logan Intl
$460

WestJet flights from Boston to Winnipeg

Our best WestJet deals on Boston to Winnipeg flight tickets
WestJet
Jun 14
BOS5:30 amBoston Logan Intl
12h 45m
2 stops
YWG5:15 pmWinnipeg
Jun 20
YWG6:15 amWinnipeg
16h 17m
2 stops
BOS11:32 pmBoston Logan Intl
$563
WestJet
Feb 4
BOS5:50 amBoston Logan Intl
6h 13m
1 stop
YWG11:03 amWinnipeg
Feb 4
YWG2:40 pmWinnipeg
20h 00m
2 stops
BOS11:40 amBoston Logan Intl
$1,307

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 February 3, 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

Fri 3/6

9:00 am-7:35 pm

1 stop11h 35m

Winnipeg

Mon 3/9

8:00 am-5:15 pm

1 stop32h 15m

$366

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 3/2

6:00 am-12:36 am

2 stops19h 36m

Winnipeg

Mon 3/9

8:00 am-5:15 pm

1 stop32h 15m

$367

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 5/14

6:35 pm-9:45 am

1 stop16h 10m

Winnipeg

Mon 5/18

6:00 am-3:50 pm

1 stop8h 50m

$368

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 3/6

6:00 am-3:09 pm

1 stop10h 09m

Winnipeg

Mon 3/9

8:00 am-5:15 pm

1 stop32h 15m

$375

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 3/5

6:10 pm-3:09 pm

2 stops21h 59m

Winnipeg

Mon 3/9

8:00 am-4:45 pm

3 stops31h 45m

$381

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 3/5

6:10 pm-3:09 pm

2 stops21h 59m

Winnipeg

Mon 3/9

8:00 am-11:44 pm

1 stop14h 44m

$382

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 3/5

6:10 pm-3:09 pm

2 stops21h 59m

Winnipeg

Mon 3/9

12:20 pm-11:44 pm

2 stops34h 24m

$385

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 3/2

5:27 am-6:03 pm

1 stop13h 36m

Winnipeg

Mon 3/9

8:00 am-5:15 pm

1 stop32h 15m

$389

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 3/6

6:00 am-12:40 am

2 stops19h 40m

Winnipeg

Mon 3/9

8:20 pm-11:05 am

1 stop13h 45m

$397

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 5/14

7:15 am-5:15 pm

1 stop11h 00m

Winnipeg

Mon 5/18

9:05 pm-12:05 pm

2 stops14h 00m

$399

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 $314.

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 $438 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 $199 on momondo.

How have Boston to Winnipeg flight prices changed over time?

As of February 2026, prices for Boston to Winnipeg flights are approximately 12% 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 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

  • 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?

  • 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 $128Free CancellationRating
7.1
10,685 reviews
Search Air Canada flights
DeltaPriceFrom $131Free CancellationRating
7.9
8,139 reviews
Search Delta flights
United AirlinesPriceFrom $172Free CancellationRating
7.4
9,236 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
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.

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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