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Cheap flights from Winnipeg to Boston from C$ 250

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 9/9. 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
1 adult, Economy, 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
12:15 p.m. - 6:35 p.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 20m1 stop Toronto Pearson Intl
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 14m1 stop Toronto Pearson Intl
C$ 447Porter Airlines
Tue, 1 Sep - Tue, 8 Sep
Porter Airlines Logo
12:15 p.m. - 6:35 p.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 20m1 stop Toronto Pearson Intl
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 14m1 stop Toronto Pearson Intl
C$ 455Porter Airlines
Mon, 7 Sep - Thu, 17 Sep
Porter Airlines Logo
12:15 p.m. - 6:35 p.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 20m1 stop Toronto Pearson Intl
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 14m1 stop Toronto Pearson Intl
C$ 455Porter Airlines
Thu, 3 Sep - Tue, 8 Sep
Air Canada Logo
8:10 a.m. - 2:41 p.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 31m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
5:30 a.m. - 11:20 a.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 50m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 462Air Canada
Thu, 22 Oct - Sun, 25 Oct
Multiple Airlines Logo
7:45 a.m. - 6:35 p.m.YWG  Winnipeg-BOS Boston Logan Intl
9h 50m1 stop Toronto Pearson Intl
Multiple Airlines Logo
10:05 a.m. - 5:15 p.m.BOS  Boston Logan Intl-YWG Winnipeg
8h 10m1 stop Toronto Pearson Intl
C$ 466Multiple Airlines
Wed, 16 Sep - Wed, 23 Sep
United Airlines Logo
7:00 a.m. - 12:54 a.m.YWG  Winnipeg-BOS Boston Logan Intl
16h 54m1 stop Chicago O'Hare Intl
United Airlines Logo
7:01 a.m. - 10:33 p.m.BOS  Boston Logan Intl-YWG Winnipeg
16h 32m1 stop Chicago O'Hare Intl
C$ 473United Airlines
Fri, 2 Oct - Mon, 5 Oct
United Airlines Logo
2:00 p.m. - 1:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
10h 10m1 stop Chicago O'Hare Intl
United Airlines Logo
8:21 p.m. - 11:52 a.m.BOS  Boston Logan Intl-YWG Winnipeg
16h 31m1 stop Chicago O'Hare Intl
C$ 473United Airlines
Thu, 17 Sep - Sat, 19 Sep
Air Canada Logo
1:25 p.m. - 9:26 p.m.YWG  Winnipeg-BOS Boston Logan Intl
7h 01m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
5:50 a.m. - 12:29 p.m.BOS  Boston Logan Intl-YWG Winnipeg
7h 39m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 475Air Canada
Fri, 16 Oct - Fri, 23 Oct
Multiple Airlines Logo
6:15 a.m. - 6:35 p.m.YWG  Winnipeg-BOS Boston Logan Intl
11h 20m1 stop Toronto Pearson Intl
Multiple Airlines Logo
2:20 p.m. - 9:45 a.m.BOS  Boston Logan Intl-YWG Winnipeg
20h 25m2 stops Ottawa Toronto Pearson Intl
C$ 475Multiple Airlines
Wed, 16 Sep - Wed, 23 Sep
Air Canada Logo
1:25 p.m. - 9:26 p.m.YWG  Winnipeg-BOS Boston Logan Intl
7h 01m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
6:00 a.m. - 11:12 a.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 12m1 stop Toronto Pearson Intl
C$ 482Air Canada
Sat, 10 Oct - Mon, 12 Oct

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Porter Airlines flights from Winnipeg to Boston

Our best Porter Airlines deals on Winnipeg to Boston flight tickets
Porter Airlines
1 Sep
YWG12:15 p.m.Winnipeg
5h 20m
1 stop
BOS6:35 p.m.Boston Logan Intl
8 Sep
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
C$ 447
Porter Airlines
3 Sep
YWG12:15 p.m.Winnipeg
5h 20m
1 stop
BOS6:35 p.m.Boston Logan Intl
8 Sep
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
C$ 455
Porter Airlines
3 Dec
YWG11:35 a.m.Winnipeg
9h 42m
2 stops
BOS10:17 p.m.Boston Logan Intl
8 Dec
BOS1:15 p.m.Boston Logan Intl
5h 55m
1 stop
YWG6:10 p.m.Winnipeg
C$ 463

WestJet flights from Winnipeg to Boston

Our best WestJet deals on Winnipeg to Boston flight tickets
WestJet
16 Oct
YWG9:05 p.m.Winnipeg
19h 35m
1 stop
BOS5:40 p.m.Boston Logan Intl
23 Oct
BOS6:30 p.m.Boston Logan Intl
20h 35m
1 stop
YWG2:05 p.m.Winnipeg
C$ 480
WestJet
2 Oct
YWG7:10 p.m.Winnipeg
21h 30m
1 stop
BOS5:40 p.m.Boston Logan Intl
5 Oct
BOS6:30 p.m.Boston Logan Intl
18h 45m
1 stop
YWG12:15 p.m.Winnipeg
C$ 549

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 5 August 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 Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 1/9

12:15 p.m.-6:35 p.m.

1 stop5h 20m

Boston Logan Intl

Tue 8/9

10:05 a.m.-3:19 p.m.

1 stop6h 14m

C$ 447

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Mon 7/9

12:15 p.m.-6:35 p.m.

1 stop5h 20m

Boston Logan Intl

Thu 17/9

10:05 a.m.-3:19 p.m.

1 stop6h 14m

C$ 455

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 3/9

12:15 p.m.-6:35 p.m.

1 stop5h 20m

Boston Logan Intl

Tue 8/9

10:05 a.m.-3:19 p.m.

1 stop6h 14m

C$ 455

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 22/10

8:10 a.m.-2:41 p.m.

1 stop5h 31m

Boston Logan Intl

Sun 25/10

5:30 a.m.-11:20 a.m.

1 stop6h 50m

C$ 462

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 16/9

7:45 a.m.-6:35 p.m.

1 stop9h 50m

Boston Logan Intl

Wed 23/9

10:05 a.m.-5:15 p.m.

1 stop8h 10m

C$ 466

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 2/10

7:00 a.m.-12:54 a.m.

1 stop16h 54m

Boston Logan Intl

Mon 5/10

7:01 a.m.-10:33 p.m.

1 stop16h 32m

C$ 473

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 17/9

2:00 p.m.-1:10 a.m.

1 stop10h 10m

Boston Logan Intl

Sat 19/9

8:21 p.m.-11:52 a.m.

1 stop16h 31m

C$ 473

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 16/10

1:25 p.m.-9:26 p.m.

2 stops7h 01m

Boston Logan Intl

Fri 23/10

5:50 a.m.-12:29 p.m.

1 stop7h 39m

C$ 475

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 16/9

6:15 a.m.-6:35 p.m.

1 stop11h 20m

Boston Logan Intl

Wed 23/9

2:20 p.m.-9:45 a.m.

2 stops20h 25m

C$ 475

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 10/10

1:25 p.m.-9:26 p.m.

2 stops7h 01m

Boston Logan Intl

Mon 12/10

6:00 a.m.-11:12 a.m.

1 stop6h 12m

C$ 482

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

Prices are currently low for flights on this route.

Typical prices usually range from C$ 451 to C$ 608.
The lowest price recently found on this route was C$ 447.

What is the cheapest month to fly to Boston?

The cheapest month to fly to Boston from Winnipeg is in August. Flight prices, which tend to average around C$ 483, are often lower during this time because this is during the off-season. If you are unable to visit Boston during the month of August, then departing from Winnipeg during the month June is also very affordable. Most momondo users find prices during this month for around C$ 531.

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.

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

5h 20m

Direct flights

None
The fastest flight from Winnipeg to Boston takes 5h 20m
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 2161.4 km. Flights usually cover this in 5h 20m, 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$ 163Free CancellationRating
7.4
10,064 reviews
Search United Airlines flights
Porter AirlinesPriceFrom C$ 329Free CancellationRating
8.0
450 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 399Free CancellationRating
7.1
11,429 reviews
Search Air Canada flights

Travelling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Old Orchard Beach
Hampton Beach
Ogunquit
Chelsea
Kennebunkport
Needham
Everett
Wells
Warwick
Foxborough
Burlington
Scarborough
Salem
Waltham
Westbrook
Saco
Seabrook
Watertown
Woburn
Brookline

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

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