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Cheap flights from Winnipeg to Boston from $158

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Boston departing on 9/28. 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 Winnipeg to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$261Porter Airlines
Fri, Sep 25 - Wed, Sep 30
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
$270Porter Airlines
Fri, Sep 25 - Wed, Sep 30
Delta Logo
8:50 am - 7:13 pm
YWG
-
BOS
9h 23m
1 stop
Delta Logo
3:05 pm - 11:27 pm
BOS
-
YWG
9h 22m
1 stop
$272Delta
Sat, Sep 12 - Tue, Sep 15
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$275Porter Airlines
Tue, Aug 11 - Tue, Aug 18
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
7:10 am - 5:58 pm
BOS
-
YWG
11h 48m
2 stops
$280Porter Airlines
Sat, Aug 8 - Mon, Aug 10
Air Canada Logo
5:10 am - 2:41 pm
YWG
-
BOS
8h 31m
2 stops
Air Canada Logo
6:00 am - 11:15 am
BOS
-
YWG
6h 15m
1 stop
$283Air Canada
Tue, Aug 11 - Tue, Aug 18
Air Canada Logo
12:20 pm - 9:27 pm
YWG
-
BOS
8h 07m
2 stops
Air Canada Logo
6:00 am - 11:12 am
BOS
-
YWG
6h 12m
1 stop
$286Air Canada
Sat, Sep 12 - Tue, Sep 15
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
$290Porter Airlines
Tue, Aug 4 - Mon, Aug 10
Porter Airlines Logo
9:20 am - 8:55 pm
YWG
-
BOS
10h 35m
2 stops
Porter Airlines Logo
10:05 am - 5:58 pm
BOS
-
YWG
8h 53m
2 stops
$292Porter Airlines
Mon, Aug 10 - Tue, Aug 18
Air Canada Logo
7:10 pm - 9:53 am
YWG
-
BOS
13h 43m
1 stop
Air Canada Logo
6:00 am - 11:15 am
BOS
-
YWG
6h 15m
1 stop
$299Air Canada
Mon, Aug 10 - Fri, Aug 14

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Air Canada flights from Winnipeg to Boston

Our best Air Canada deals on Winnipeg to Boston flight tickets
Air Canada
Aug 11
YWG5:10 amWinnipeg
8h 31m
2 stops
BOS2:41 pmBoston Logan Intl
Aug 18
BOS6:00 amBoston Logan Intl
6h 15m
1 stop
YWG11:15 amWinnipeg
$283
Air Canada
Sep 12
YWG12:20 pmWinnipeg
8h 07m
2 stops
BOS9:27 pmBoston Logan Intl
Sep 15
BOS6:00 amBoston Logan Intl
6h 12m
1 stop
YWG11:12 amWinnipeg
$286
Air Canada
Aug 10
YWG7:10 pmWinnipeg
13h 43m
1 stop
BOS9:53 amBoston Logan Intl
Aug 14
BOS6:00 amBoston Logan Intl
6h 15m
1 stop
YWG11:15 amWinnipeg
$299

Porter Airlines flights from Winnipeg to Boston

Our best Porter Airlines deals on Winnipeg to Boston flight tickets
Porter Airlines
Sep 25
YWG9:20 amWinnipeg
7h 15m
1 stop
BOS5:35 pmBoston Logan Intl
Sep 30
BOS10:05 amBoston Logan Intl
6h 14m
1 stop
YWG3:19 pmWinnipeg
$261
Porter Airlines
Sep 25
YWG9:20 amWinnipeg
7h 15m
1 stop
BOS5:35 pmBoston Logan Intl
Sep 30
BOS7:10 amBoston Logan Intl
11h 48m
2 stops
YWG5:58 pmWinnipeg
$270
Porter Airlines
Aug 11
YWG9:20 amWinnipeg
7h 15m
1 stop
BOS5:35 pmBoston Logan Intl
Aug 18
BOS10:05 amBoston Logan Intl
6h 14m
1 stop
YWG3:19 pmWinnipeg
$275

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Boston 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 May 1, 2026.
Use the filters below to find and compare flights from Winnipeg to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 9/25

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Wed 9/30

10:05 am-3:19 pm

1 stop6h 14m

$261

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 9/25

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Wed 9/30

7:10 am-5:58 pm

2 stops11h 48m

$270

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 9/12

8:50 am-7:13 pm

1 stop9h 23m

Boston Logan Intl

Tue 9/15

3:05 pm-11:27 pm

1 stop9h 22m

$272

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 8/11

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Tue 8/18

10:05 am-3:19 pm

1 stop6h 14m

$275

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 8/8

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Mon 8/10

7:10 am-5:58 pm

2 stops11h 48m

$280

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 8/11

5:10 am-2:41 pm

2 stops8h 31m

Boston Logan Intl

Tue 8/18

6:00 am-11:15 am

1 stop6h 15m

$283

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 9/12

12:20 pm-9:27 pm

2 stops8h 07m

Boston Logan Intl

Tue 9/15

6:00 am-11:12 am

1 stop6h 12m

$286

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 8/4

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Mon 8/10

10:05 am-3:19 pm

1 stop6h 14m

$290

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 8/10

9:20 am-8:55 pm

2 stops10h 35m

Boston Logan Intl

Tue 8/18

10:05 am-5:58 pm

2 stops8h 53m

$292

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 8/10

7:10 pm-9:53 am

1 stop13h 43m

Boston Logan Intl

Fri 8/14

6:00 am-11:15 am

1 stop6h 15m

$299

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Winnipeg to Boston

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

What is the cheapest month to fly to Boston?

In general, June is the cheapest month to fly from Winnipeg to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $290. If you aren’t able to travel during the month of June, then book flights to Boston from Winnipeg during August instead. Flights to Boston in August, while not as cheap as those in June, still average around $320.

How far in advance should I book a flight from Winnipeg to Boston?

You are more likely to see cheaper flights to Boston from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $505 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Winnipeg for as low as $246 on momondo.

How have Winnipeg to Boston flight prices changed over time?

When to book flights from Winnipeg to Boston

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Boston according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Winnipeg to Boston (YWG to BOS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Boston

Fastest flight time

7h 15m

Direct flights

None
The fastest flight from Winnipeg to Boston takes 7h 15m
There are no direct flights from Winnipeg to Boston. There are no popular flight routes from Winnipeg to Boston.
Search flight deals

Frequently asked questions about flying from Winnipeg to Boston

  • How far is Winnipeg to Boston Logan Intl by plane?

    The straight-line distance from Winnipeg to Boston Logan Intl is 1343.0 mi. 7h 15m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Winnipeg Airport to Boston Logan Intl Airport?

    Prices for flights from Winnipeg Airport to Boston Logan Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Winnipeg Airport to Boston Logan Intl Airport?

  • How old do you have to be to fly from Winnipeg Airport to Boston Logan Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Winnipeg Airport to Boston Logan Intl Airport.

  • What documentation or ID do you need to fly to Boston Logan Intl Airport?

    The necessary travel and health documents for your Boston Logan Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Winnipeg to Boston?

Best airlines flying from Winnipeg to Boston

Compare and see reviews for airlines that fly from Winnipeg to Boston with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $168Free CancellationRating
7.4
9,675 reviews
Search United Airlines flights
Air CanadaPriceFrom $215Free CancellationRating
7.1
10,983 reviews
Search Air Canada flights

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Hampton Beach
Salem
Ogunquit
Old Orchard Beach
Hampton
York Beach
Kennebunkport
Plymouth
Cambridge
South Yarmouth
Gloucester
Narragansett
Brockton
Falmouth
Chatham
Warwick
Sturbridge
Laconia
Dennis Port
Nashua

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Boston?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Winnipeg to Boston. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Winnipeg to Boston with flexible booking policies on momondo?

Yes. All flights to Boston from Winnipeg on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Winnipeg to Boston?

Once you have performed a search for Winnipeg to Boston flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Winnipeg to Boston right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Winnipeg to Boston flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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