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Cheap flights from Winnipeg to Boston from C$ 201

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 25/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Winnipeg to Boston

Cheap round-trip flights

Delta Logo
5:40 p.m. - 11:59 p.m.YWG-BOS
5h 19m1 stop
Delta Logo
5:45 a.m. - 11:30 a.m.BOS-YWG
6h 45m1 stop
C$ 346Delta
Find Deal
Tue, 7 Oct - Wed, 15 Oct
Logo
7:30 a.m. - 1:04 a.m.YWG-BOS
16h 34m1 stop
Logo
6:00 a.m. - 3:07 p.m.BOS-YWG
10h 07m1 stop
C$ 408
Find Deal
Fri, 23 Jan - Sun, 25 Jan
Air Canada Logo
8:15 a.m. - 2:52 p.m.YWG-BOS
5h 37m1 stop
Air Canada Logo
5:30 a.m. - 10:16 a.m.BOS-YWG
5h 46m1 stop
C$ 453Air Canada
Find Deal
Tue, 25 Nov - Sun, 30 Nov
Air Canada Logo
8:15 a.m. - 2:52 p.m.YWG-BOS
5h 37m1 stop
Air Canada Logo
10:15 a.m. - 4:35 p.m.BOS-YWG
7h 20m1 stop
C$ 464Air Canada
Find Deal
Fri, 6 Mar - Sun, 8 Mar
United Airlines Logo
2:20 p.m. - 12:45 a.m.YWG-BOS
9h 25m1 stop
United Airlines Logo
8:30 p.m. - 11:57 a.m.BOS-YWG
16h 27m1 stop
C$ 471United Airlines
Find Deal
Fri, 14 Nov - Sun, 16 Nov
United Airlines Logo
2:20 p.m. - 11:49 p.m.YWG-BOS
8h 29m2 stops
United Airlines Logo
6:17 p.m. - 11:57 a.m.BOS-YWG
18h 40m2 stops
C$ 472United Airlines
Find Deal
Fri, 23 Jan - Sun, 25 Jan
Air Canada Logo
5:00 a.m. - 11:29 a.m.YWG-BOS
5h 29m1 stop
Air Canada Logo
6:00 a.m. - 4:15 p.m.BOS-YWG
11h 15m2 stops
C$ 502Air Canada
Find Deal
Tue, 7 Oct - Wed, 15 Oct
Air Canada Logo
7:05 p.m. - 9:32 a.m.YWG-BOS
13h 27m2 stops
Air Canada Logo
5:30 a.m. - 10:16 a.m.BOS-YWG
5h 46m1 stop
C$ 512Air Canada
Find Deal
Fri, 14 Nov - Sun, 16 Nov
WestJet Logo
6:30 a.m. - 11:59 p.m.YWG-BOS
16h 29m2 stops
WestJet Logo
8:10 a.m. - 9:25 p.m.BOS-YWG
14h 15m2 stops
C$ 880WestJet
Find Deal
Tue, 7 Oct - Wed, 15 Oct
WestJet Logo
6:30 a.m. - 4:05 p.m.YWG-BOS
8h 35m2 stops
WestJet Logo
1:05 p.m. - 11:10 p.m.BOS-YWG
11h 05m2 stops
C$ 932WestJet
Find Deal
Tue, 7 Oct - Wed, 15 Oct

Air Canada flights from Winnipeg to Boston

Our best Air Canada deals on Winnipeg to Boston flight tickets
Air Canada
25 Nov
YWG8:15 a.m.Winnipeg
5h 37m
1 stop
BOS2:52 p.m.Boston Logan Intl
30 Nov
BOS5:30 a.m.Boston Logan Intl
5h 46m
1 stop
YWG10:16 a.m.Winnipeg
C$ 453
Find similar
Air Canada
6 Mar
YWG8:15 a.m.Winnipeg
5h 37m
1 stop
BOS2:52 p.m.Boston Logan Intl
8 Mar
BOS10:15 a.m.Boston Logan Intl
7h 20m
1 stop
YWG4:35 p.m.Winnipeg
C$ 464
Find similar
Air Canada
7 Oct
YWG5:00 a.m.Winnipeg
5h 29m
1 stop
BOS11:29 a.m.Boston Logan Intl
15 Oct
BOS6:00 a.m.Boston Logan Intl
11h 15m
2 stops
YWG4:15 p.m.Winnipeg
C$ 502
Find similar

United Airlines flights from Winnipeg to Boston

Our best United Airlines deals on Winnipeg to Boston flight tickets
United Airlines
14 Nov
YWG2:20 p.m.Winnipeg
9h 25m
1 stop
BOS12:45 a.m.Boston Logan Intl
16 Nov
BOS8:30 p.m.Boston Logan Intl
16h 27m
1 stop
YWG11:57 a.m.Winnipeg
C$ 471
Find similar
United Airlines
23 Jan
YWG2:20 p.m.Winnipeg
8h 29m
2 stops
BOS11:49 p.m.Boston Logan Intl
25 Jan
BOS6:17 p.m.Boston Logan Intl
18h 40m
2 stops
YWG11:57 a.m.Winnipeg
C$ 472
Find similar
United Airlines
12 Oct
YWG5:00 a.m.Winnipeg
5h 29m
1 stop
BOS11:29 a.m.Boston Logan Intl
19 Oct
BOS6:00 a.m.Boston Logan Intl
17h 33m
1 stop
YWG10:33 p.m.Winnipeg
C$ 639
Find similar

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 96,600 searches. Data last updated 15 September 2025.
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

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 7/10

5:40 p.m.-11:59 p.m.

1 stop5h 19m

Boston Logan Intl

Wed 15/10

5:45 a.m.-11:30 a.m.

1 stop6h 45m

C$ 346

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 23/1

7:30 a.m.-1:04 a.m.

1 stop16h 34m

Boston Logan Intl

Sun 25/1

6:00 a.m.-3:07 p.m.

1 stop10h 07m

C$ 408

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 25/11

8:15 a.m.-2:52 p.m.

1 stop5h 37m

Boston Logan Intl

Sun 30/11

5:30 a.m.-10:16 a.m.

1 stop5h 46m

C$ 453

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 6/3

8:15 a.m.-2:52 p.m.

1 stop5h 37m

Boston Logan Intl

Sun 8/3

10:15 a.m.-4:35 p.m.

1 stop7h 20m

C$ 464

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 14/11

2:20 p.m.-12:45 a.m.

1 stop9h 25m

Boston Logan Intl

Sun 16/11

8:30 p.m.-11:57 a.m.

1 stop16h 27m

C$ 471

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 23/1

2:20 p.m.-11:49 p.m.

2 stops8h 29m

Boston Logan Intl

Sun 25/1

6:17 p.m.-11:57 a.m.

2 stops18h 40m

C$ 472

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 7/10

5:00 a.m.-11:29 a.m.

1 stop5h 29m

Boston Logan Intl

Wed 15/10

6:00 a.m.-4:15 p.m.

2 stops11h 15m

C$ 502

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 14/11

7:05 p.m.-9:32 a.m.

2 stops13h 27m

Boston Logan Intl

Sun 16/11

5:30 a.m.-10:16 a.m.

1 stop5h 46m

C$ 512

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 7/10

6:30 a.m.-11:59 p.m.

2 stops16h 29m

Boston Logan Intl

Wed 15/10

8:10 a.m.-9:25 p.m.

2 stops14h 15m

C$ 880

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 7/10

6:30 a.m.-4:05 p.m.

2 stops8h 35m

Boston Logan Intl

Wed 15/10

1:05 p.m.-11:10 p.m.

2 stops11h 05m

C$ 932

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 Boston from

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 cheapest month to fly to Boston?

The cheapest month to fly to Boston from Winnipeg is in October. Flight prices, which tend to average around C$ 424, are often lower during this time because this is during the off-season. If you are unable to visit Boston during the month of October, then departing from Winnipeg during the month August is also very affordable. Most momondo users find prices during this month for around C$ 451.

What is the cheapest day to depart on your flight to Boston?

On average, the least expensive day to fly to Boston from Winnipeg is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as C$ 427. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Winnipeg to Boston on a Sunday will generally be more expensive and average around C$ 622. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Boston?

Flying to Boston from Winnipeg in the morning is the least expensive time of day to depart. momondo users have found prices as low as C$ 538 when looking at flights departing in the morning. Flights in the afternoon are often more expensive with an average ticket price of C$ 650.

How far in advance should I book a flight 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 C$ 557 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 C$ 335 on momondo.

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

Direct flights

None
There are no direct flights from Winnipeg to Boston. There are no popular flight routes from Winnipeg to Boston.
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  • How far is Winnipeg to Boston Logan Intl by plane?

    The straight-line distance from Winnipeg to Boston Logan Intl is 2161.4 km. Flights usually cover this in 5h 19m, depending on flying conditions and air traffic around both airports.

  • 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 for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for 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 C$ 239Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
Porter AirlinesPriceFrom C$ 290Free CancellationRating
7.9
363 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 323Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
DeltaPriceFrom C$ 368Free CancellationRating
7.9
7,954 reviews
Search Delta flights
WestJetPriceFrom C$ 474Free CancellationRating
7.2
3,091 reviews
Search WestJet flights

Travelling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Hampton Beach
Old Orchard Beach
Salem
Ogunquit
Wells
Cambridge
Everett
Needham
Newton
West Yarmouth
Saco
Middletown
Westbrook
Burlington
Sturbridge
Scarborough
Cape Neddick
Waltham
Quincy
Peabody

Why use momondo?

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

It is quick and easy to find Winnipeg to Boston 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 Boston that suits you.

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

Yes. momondo enables you to select and highlight flights to Boston from Winnipeg with this policy.

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?

If you are simply researching potential flights to Boston, momondo offers a useful price alert feature which will track prices for flights to Boston from Winnipeg and alert you when they change.

An easier way to manage your Boston 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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