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Cheap flights from Winnipeg to Boston from C$ 182

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 30/1. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
12:55 p.m. - 1:13 a.m.
YWG
-
BOS
35h 18m2 stops
Multiple Airlines Logo
6:00 a.m. - 3:09 p.m.
BOS
-
YWG
10h 09m1 stop
C$ 400Multiple Airlines
Fri, 30 Jan - Fri, 6 Feb
Multiple Airlines Logo
5:00 a.m. - 11:05 a.m.
YWG
-
BOS
29h 05m1 stop
Multiple Airlines Logo
6:00 a.m. - 12:41 a.m.
BOS
-
YWG
19h 41m2 stops
C$ 424Multiple Airlines
Thu, 15 Jan - Thu, 22 Jan
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$ 438Air Canada
Thu, 15 Jan - Thu, 22 Jan
Air Canada Logo
5:30 a.m. - 12:12 p.m.
YWG
-
BOS
5h 42m1 stop
Air Canada Logo
5:30 a.m. - 10:16 a.m.
BOS
-
YWG
5h 46m1 stop
C$ 442Air Canada
Fri, 9 Jan - Sun, 11 Jan
Air Canada Logo
6:00 a.m. - 2:52 p.m.
YWG
-
BOS
7h 52m2 stops
Air Canada Logo
10:15 a.m. - 4:35 p.m.
BOS
-
YWG
7h 20m1 stop
C$ 445Air Canada
Fri, 9 Jan - Sun, 11 Jan
Air Canada Logo
8:15 a.m. - 2:52 p.m.
YWG
-
BOS
5h 37m1 stop
Air Canada Logo
5:30 a.m. - 10:15 a.m.
BOS
-
YWG
5h 45m1 stop
C$ 453Air Canada
Fri, 13 Feb - Sun, 15 Feb
Air Canada Logo
5:30 p.m. - 10:02 a.m.
YWG
-
BOS
15h 32m1 stop
Air Canada Logo
10:15 a.m. - 4:35 p.m.
BOS
-
YWG
7h 20m1 stop
C$ 475Air Canada
Fri, 30 Jan - Fri, 6 Feb
Multiple Airlines Logo
12:20 p.m. - 4:28 p.m.
YWG
-
BOS
27h 08m3 stops
Multiple Airlines Logo
5:27 p.m. - 3:30 p.m.
BOS
-
YWG
23h 03m2 stops
C$ 484Multiple Airlines
Thu, 15 Jan - Thu, 22 Jan
Multiple Airlines Logo
5:00 a.m. - 6:10 p.m.
YWG
-
BOS
12h 10m2 stops
Multiple Airlines Logo
5:27 p.m. - 3:30 p.m.
BOS
-
YWG
23h 03m2 stops
C$ 497Multiple Airlines
Thu, 15 Jan - Thu, 22 Jan
Multiple Airlines Logo
12:20 p.m. - 4:28 p.m.
YWG
-
BOS
27h 08m3 stops
Multiple Airlines Logo
5:34 a.m. - 12:41 a.m.
BOS
-
YWG
20h 07m3 stops
C$ 510Multiple Airlines
Thu, 15 Jan - Thu, 22 Jan

Air Canada flights from Winnipeg to Boston

Our best Air Canada deals on Winnipeg to Boston flight tickets
Air Canada
15 Jan
YWG8:15 a.m.Winnipeg
5h 37m
1 stop
BOS2:52 p.m.Boston Logan Intl
22 Jan
BOS10:15 a.m.Boston Logan Intl
7h 20m
1 stop
YWG4:35 p.m.Winnipeg
C$ 438
Find similar
Air Canada
9 Jan
YWG5:30 a.m.Winnipeg
5h 42m
1 stop
BOS12:12 p.m.Boston Logan Intl
11 Jan
BOS5:30 a.m.Boston Logan Intl
5h 46m
1 stop
YWG10:16 a.m.Winnipeg
C$ 442
Find similar
Air Canada
9 Jan
YWG6:00 a.m.Winnipeg
7h 52m
2 stops
BOS2:52 p.m.Boston Logan Intl
11 Jan
BOS10:15 a.m.Boston Logan Intl
7h 20m
1 stop
YWG4:35 p.m.Winnipeg
C$ 445
Find similar

United Airlines flights from Winnipeg to Boston

Our best United Airlines deals on Winnipeg to Boston flight tickets
United Airlines
2 Feb
YWG2:20 p.m.Winnipeg
8h 29m
2 stops
BOS11:49 p.m.Boston Logan Intl
3 Feb
BOS6:00 a.m.Boston Logan Intl
6h 57m
1 stop
YWG11:57 a.m.Winnipeg
C$ 620
Find similar
United Airlines
2 Feb
YWG2:20 p.m.Winnipeg
6h 18m
1 stop
BOS9:38 p.m.Boston Logan Intl
3 Feb
BOS6:00 a.m.Boston Logan Intl
6h 57m
1 stop
YWG11:57 a.m.Winnipeg
C$ 630
Find similar
United Airlines
13 Mar
YWG5:30 a.m.Winnipeg
15h 18m
2 stops
BOS9:48 p.m.Boston Logan Intl
15 Mar
BOS6:00 a.m.Boston Logan Intl
6h 57m
1 stop
YWG11:57 a.m.Winnipeg
C$ 681
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 18 December 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

Fri 30/1

12:55 p.m.-1:13 a.m.

2 stops35h 18m

Boston Logan Intl

Fri 6/2

6:00 a.m.-3:09 p.m.

1 stop10h 09m

C$ 400

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 15/1

5:00 a.m.-11:05 a.m.

1 stop29h 05m

Boston Logan Intl

Thu 22/1

6:00 a.m.-12:41 a.m.

2 stops19h 41m

C$ 424

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 15/1

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

1 stop5h 37m

Boston Logan Intl

Thu 22/1

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

1 stop7h 20m

C$ 438

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 9/1

5:30 a.m.-12:12 p.m.

1 stop5h 42m

Boston Logan Intl

Sun 11/1

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

1 stop5h 46m

C$ 442

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 9/1

6:00 a.m.-2:52 p.m.

2 stops7h 52m

Boston Logan Intl

Sun 11/1

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

1 stop7h 20m

C$ 445

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 13/2

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

1 stop5h 37m

Boston Logan Intl

Sun 15/2

5:30 a.m.-10:15 a.m.

1 stop5h 45m

C$ 453

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 30/1

5:30 p.m.-10:02 a.m.

1 stop15h 32m

Boston Logan Intl

Fri 6/2

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

1 stop7h 20m

C$ 475

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 15/1

12:20 p.m.-4:28 p.m.

3 stops27h 08m

Boston Logan Intl

Thu 22/1

5:27 p.m.-3:30 p.m.

2 stops23h 03m

C$ 484

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 15/1

5:00 a.m.-6:10 p.m.

2 stops12h 10m

Boston Logan Intl

Thu 22/1

5:27 p.m.-3:30 p.m.

2 stops23h 03m

C$ 497

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 15/1

12:20 p.m.-4:28 p.m.

3 stops27h 08m

Boston Logan Intl

Thu 22/1

5:34 a.m.-12:41 a.m.

3 stops20h 07m

C$ 510

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 June. Flight prices, which tend to average around C$ 408, are often lower during this time because this is during the off-season. If you are unable to visit Boston during the month of June, then departing from Winnipeg during the month August is also very affordable. Most momondo users find prices during this month for around C$ 441.

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$ 425. 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$ 620. 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$ 535 when looking at flights departing in the morning. Flights in the afternoon are often more expensive with an average ticket price of C$ 647.

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$ 578 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$ 333 on momondo.

Can stopping save me money on Winnipeg to Boston flights?

You could potentially save up to 35% on your flight if you consider stops on a Winnipeg to Boston flight.

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

5h 42m

Direct flights

None
The fastest flight from Winnipeg to Boston takes 5h 42m
There are no direct flights from Winnipeg to Boston. There are no popular flight routes from Winnipeg to Boston.
Search flight deals

  • 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 42m, 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$ 238Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 350Free CancellationRating
7.1
10,532 reviews
Search Air Canada flights
Porter AirlinesPriceFrom C$ 421Free CancellationRating
8.0
399 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 472Free CancellationRating
7.2
3,203 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
Ogunquit
Everett
Wells
Cambridge
Waltham
Dedham
West Yarmouth
Needham
Salem
Saco
Westbrook
Burlington
Sturbridge
Scarborough
Cape Neddick
Quincy
Middletown
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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