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Cheap flights from Boston to Winnipeg from C$ 287

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Boston to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
1:15 p.m. - 7:06 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 51m1 stop Ottawa
Multiple Airlines Logo
7:55 p.m. - 9:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
13h 15m1 stop Toronto Pearson Intl
C$ 534Multiple Airlines
Sat, 21 Nov - Mon, 30 Nov
Multiple Airlines Logo
1:15 p.m. - 7:06 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 51m1 stop Ottawa
Multiple Airlines Logo
7:55 p.m. - 4:46 p.m.YWG  Winnipeg-BOS Boston Logan Intl
20h 51m2 stops Toronto Pearson Intl Ottawa
C$ 541Multiple Airlines
Sat, 21 Nov - Mon, 30 Nov
Porter Airlines Logo
8:00 a.m. - 7:10 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 10m2 stops Toronto Island Ottawa
Porter Airlines Logo
11:40 a.m. - 9:42 p.m.YWG  Winnipeg-BOS Boston Logan Intl
10h 02m2 stops Ottawa Toronto Island
C$ 542Porter Airlines
Thu, 4 Feb - Tue, 9 Feb
Porter Airlines Logo
1:15 p.m. - 7:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 04m1 stop Ottawa
Porter Airlines Logo
12:40 p.m. - 9:34 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 54m2 stops Ottawa Toronto Island
C$ 565Porter Airlines
Tue, 2 Mar - Fri, 5 Mar
Porter Airlines Logo
1:15 p.m. - 7:10 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 55m1 stop Ottawa
Porter Airlines Logo
11:40 a.m. - 9:42 p.m.YWG  Winnipeg-BOS Boston Logan Intl
10h 02m2 stops Ottawa Toronto Island
C$ 580Porter Airlines
Thu, 4 Feb - Tue, 9 Feb
Multiple Airlines Logo
5:25 p.m. - 10:15 a.m.BOS  Boston Logan Intl-YWG Winnipeg
16h 50m1 stop Toronto Pearson Intl
Multiple Airlines Logo
7:55 p.m. - 9:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
13h 15m1 stop Toronto Pearson Intl
C$ 622Multiple Airlines
Thu, 26 Nov - Mon, 30 Nov
Porter Airlines Logo
1:15 p.m. - 7:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 04m1 stop Ottawa
Porter Airlines Logo
12:40 p.m. - 9:34 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 54m2 stops Ottawa Toronto Island
C$ 646Porter Airlines
Mon, 1 Mar - Tue, 9 Mar
Multiple Airlines Logo
8:00 a.m. - 10:15 a.m.BOS  Boston Logan Intl-YWG Winnipeg
26h 15m1 stop Toronto Island
Multiple Airlines Logo
11:00 a.m. - 4:46 p.m.YWG  Winnipeg-BOS Boston Logan Intl
29h 46m2 stops Toronto Pearson Intl Ottawa
C$ 657Multiple Airlines
Sun, 29 Nov - Thu, 3 Dec
Multiple Airlines Logo
8:00 a.m. - 10:15 a.m.BOS  Boston Logan Intl-YWG Winnipeg
26h 15m1 stop Toronto Island
Multiple Airlines Logo
11:00 a.m. - 7:10 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 10m1 stop Toronto Pearson Intl
C$ 660Multiple Airlines
Sun, 29 Nov - Thu, 3 Dec
Porter Airlines Logo
1:15 p.m. - 7:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 04m1 stop Ottawa
Porter Airlines Logo
12:40 p.m. - 9:44 p.m.YWG  Winnipeg-BOS Boston Logan Intl
9h 04m2 stops Ottawa Toronto Island
C$ 665Porter Airlines
Mon, 1 Mar - Tue, 9 Mar

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Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets
Porter Airlines
1 Mar
BOS1:15 p.m.Boston Logan Intl
6h 04m
1 stop
YWG7:19 p.m.Winnipeg
9 Mar
YWG12:40 p.m.Winnipeg
8h 54m
2 stops
BOS9:34 p.m.Boston Logan Intl
C$ 562
Porter Airlines
2 Mar
BOS1:15 p.m.Boston Logan Intl
6h 04m
1 stop
YWG7:19 p.m.Winnipeg
5 Mar
YWG12:40 p.m.Winnipeg
8h 54m
2 stops
BOS9:34 p.m.Boston Logan Intl
C$ 565
Porter Airlines
1 Mar
BOS8:00 a.m.Boston Logan Intl
11h 19m
2 stops
YWG7:19 p.m.Winnipeg
9 Mar
YWG12:40 p.m.Winnipeg
8h 54m
2 stops
BOS9:34 p.m.Boston Logan Intl
C$ 577

momondo Fare Finder

 
Use the filters below to find and compare flights from Boston to Winnipeg that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 21/11

1:15 p.m.-7:06 p.m.

1 stop5h 51m

Winnipeg

Mon 30/11

7:55 p.m.-9:10 a.m.

1 stop13h 15m

C$ 534

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 21/11

1:15 p.m.-7:06 p.m.

1 stop5h 51m

Winnipeg

Mon 30/11

7:55 p.m.-4:46 p.m.

2 stops20h 51m

C$ 541

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 4/2

8:00 a.m.-7:10 p.m.

2 stops11h 10m

Winnipeg

Tue 9/2

11:40 a.m.-9:42 p.m.

2 stops10h 02m

C$ 542
Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 2/3

1:15 p.m.-7:19 p.m.

1 stop6h 04m

Winnipeg

Fri 5/3

12:40 p.m.-9:34 p.m.

2 stops8h 54m

C$ 565

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 4/2

1:15 p.m.-7:10 p.m.

1 stop5h 55m

Winnipeg

Tue 9/2

11:40 a.m.-9:42 p.m.

2 stops10h 02m

C$ 580

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 26/11

5:25 p.m.-10:15 a.m.

1 stop16h 50m

Winnipeg

Mon 30/11

7:55 p.m.-9:10 a.m.

1 stop13h 15m

C$ 622

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 1/3

1:15 p.m.-7:19 p.m.

1 stop6h 04m

Winnipeg

Tue 9/3

12:40 p.m.-9:34 p.m.

2 stops8h 54m

C$ 646

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sun 29/11

8:00 a.m.-10:15 a.m.

1 stop26h 15m

Winnipeg

Thu 3/12

11:00 a.m.-4:46 p.m.

2 stops29h 46m

C$ 657

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sun 29/11

8:00 a.m.-10:15 a.m.

1 stop26h 15m

Winnipeg

Thu 3/12

11:00 a.m.-7:10 p.m.

1 stop8h 10m

C$ 660

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 1/3

1:15 p.m.-7:19 p.m.

1 stop6h 04m

Winnipeg

Tue 9/3

12:40 p.m.-9:44 p.m.

2 stops9h 04m

C$ 665

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

Prices are currently low for flights on this route.

Typical prices usually range from C$ 738 to C$ 1,099.
The lowest price recently found on this route was C$ 534.

What is the cheapest month to fly to Winnipeg?

The cheapest month to fly to Winnipeg from Boston is in September. Flight prices, which tend to average around C$ 509, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of September, then departing from Boston during the month October is also very affordable. Most momondo users find prices during this month for around C$ 512.

Can stopping save me money on Boston to Winnipeg flights?

You could potentially save up to 27% on your flight if you consider stops on a Boston to Winnipeg flight.

How have Boston to Winnipeg flight prices changed over time?

As of November 2026, prices for Boston to Winnipeg flights are approximately 218% more expensive 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

Best price found

C$ 287

Fastest flight time

5h 51m

Direct flights

None
The best one-way flight to Winnipeg from Boston in the past 72 hours is C$ 287. The best round-trip flight deal from Boston to Winnipeg found on momondo in the last 72 hours is C$ 534.
The fastest flight from Boston to Winnipeg takes 5h 51m
There are no direct flights from Boston to Winnipeg. There are no popular flight routes from Boston to Winnipeg.
Search flight deals

Frequently asked questions about flying from Boston to Winnipeg

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

    The straight-line distance from Boston Logan Intl to Winnipeg is 2161.4 km. 5h 51m is a normal flight duration for this route.

  • 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 refreshed on a daily basis.

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

  • What documentation or ID do you need to fly to Winnipeg Airport?

    The travel and health documents you'll need for your trip to Winnipeg Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Winnipeg Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie
Morden
Selkirk

Why use momondo?

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

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

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

All flight searches from Boston to Winnipeg on momondo can be filtered to show those which offer flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Boston to Winnipeg.

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

If you are not ready to book a flight from Boston to Winnipeg now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Winnipeg and let you know when they change.

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