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Cheap flights from Boston to Winnipeg from C$ 168

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.
Air Canada Logo
3:35 p.m. - 11:47 p.m.BOS  Boston Logan Intl-YWG Winnipeg
9h 12m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
1:30 p.m. - 9:26 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 56m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
C$ 362Air Canada
Fri, 2 Oct - Sun, 11 Oct
Air Canada Logo
6:00 a.m. - 11:12 a.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 12m1 stop Toronto Pearson Intl
Air Canada Logo
1:30 p.m. - 9:26 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 56m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
C$ 363Air Canada
Fri, 2 Oct - Sun, 11 Oct
Air Canada Logo
7:05 p.m. - 11:47 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 42m1 stop Toronto Pearson Intl
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
C$ 369Air Canada
Fri, 2 Oct - Sun, 11 Oct
Multiple Airlines Logo
10:05 a.m. - 3:20 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
6:00 a.m. - 5:40 p.m.YWG  Winnipeg-BOS Boston Logan Intl
10h 40m1 stop Calgary
C$ 381Multiple Airlines
Fri, 16 Oct - Mon, 19 Oct
Multiple Airlines Logo
1:15 p.m. - 6:10 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 55m1 stop Ottawa
Multiple Airlines Logo
6:55 p.m. - 9:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
13h 15m1 stop Toronto Pearson Intl
C$ 393Multiple Airlines
Wed, 28 Oct - Sun, 1 Nov
Multiple Airlines Logo
10:05 a.m. - 3:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 14m1 stop Toronto Pearson Intl
Multiple Airlines Logo
7:45 a.m. - 6:35 p.m.YWG  Winnipeg-BOS Boston Logan Intl
9h 50m1 stop Toronto Pearson Intl
C$ 399Multiple Airlines
Wed, 30 Sep - Wed, 7 Oct
Air Canada Logo
12:45 p.m. - 6:12 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 27m1 stop Toronto Pearson Intl
Air Canada Logo
1:30 p.m. - 9:27 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 57m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 409Air Canada
Thu, 22 Oct - Sat, 24 Oct
United Airlines Logo
6:00 a.m. - 12:37 p.m.BOS  Boston Logan Intl-YWG Winnipeg
7h 37m1 stop Chicago O'Hare Intl
United Airlines Logo
7:00 a.m. - 12:54 a.m.YWG  Winnipeg-BOS Boston Logan Intl
16h 54m1 stop Chicago O'Hare Intl
C$ 413United Airlines
Fri, 16 Oct - Fri, 23 Oct
Air Canada Logo
4:55 p.m. - 11:27 p.m.BOS  Boston Logan Intl-YWG Winnipeg
7h 32m1 stop Toronto Pearson Intl
Air Canada Logo
5:00 a.m. - 11:51 a.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 51m1 stop Toronto Pearson Intl
C$ 416Air Canada
Tue, 15 Sep - Sat, 19 Sep
Multiple Airlines Logo
3:13 p.m. - 10:33 p.m.BOS  Boston Logan Intl-YWG Winnipeg
8h 20m1 stop Chicago O'Hare Intl
Multiple Airlines Logo
1:30 p.m. - 9:26 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 56m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
C$ 418Multiple Airlines
Tue, 15 Sep - Sat, 19 Sep

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Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets
Porter Airlines
30 Oct
BOS1:15 p.m.Boston Logan Intl
5h 55m
1 stop
YWG6:10 p.m.Winnipeg
2 Nov
YWG11:40 a.m.Winnipeg
8h 52m
2 stops
BOS9:32 p.m.Boston Logan Intl
C$ 490
Porter Airlines
30 Oct
BOS8:00 a.m.Boston Logan Intl
11h 10m
2 stops
YWG6:10 p.m.Winnipeg
2 Nov
YWG11:40 a.m.Winnipeg
8h 52m
2 stops
BOS9:32 p.m.Boston Logan Intl
C$ 501
Porter Airlines
30 Oct
BOS8:00 a.m.Boston Logan Intl
11h 10m
2 stops
YWG6:10 p.m.Winnipeg
2 Nov
YWG11:40 a.m.Winnipeg
8h 52m
2 stops
BOS9:32 p.m.Boston Logan Intl
C$ 526

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets
Air Canada
2 Oct
BOS3:35 p.m.Boston Logan Intl
9h 12m
2 stops
YWG11:47 p.m.Winnipeg
11 Oct
YWG1:30 p.m.Winnipeg
6h 56m
2 stops
BOS9:26 p.m.Boston Logan Intl
C$ 362
Air Canada
2 Oct
BOS6:00 a.m.Boston Logan Intl
6h 12m
1 stop
YWG11:12 a.m.Winnipeg
11 Oct
YWG1:30 p.m.Winnipeg
6h 56m
2 stops
BOS9:26 p.m.Boston Logan Intl
C$ 363
Air Canada
2 Oct
BOS7:05 p.m.Boston Logan Intl
5h 42m
1 stop
YWG11:47 p.m.Winnipeg
11 Oct
YWG8:10 a.m.Winnipeg
5h 31m
1 stop
BOS2:41 p.m.Boston Logan Intl
C$ 369

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

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Price

Cheapest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 2/10

3:35 p.m.-11:47 p.m.

2 stops9h 12m

Winnipeg

Sun 11/10

1:30 p.m.-9:26 p.m.

2 stops6h 56m

C$ 362

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 2/10

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

1 stop6h 12m

Winnipeg

Sun 11/10

1:30 p.m.-9:26 p.m.

2 stops6h 56m

C$ 363
Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 2/10

7:05 p.m.-11:47 p.m.

1 stop5h 42m

Winnipeg

Sun 11/10

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

1 stop5h 31m

C$ 369

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 16/10

10:05 a.m.-3:20 p.m.

1 stop6h 15m

Winnipeg

Mon 19/10

6:00 a.m.-5:40 p.m.

1 stop10h 40m

C$ 381

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 28/10

1:15 p.m.-6:10 p.m.

1 stop5h 55m

Winnipeg

Sun 1/11

6:55 p.m.-9:10 a.m.

1 stop13h 15m

C$ 393

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 30/9

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

1 stop6h 14m

Winnipeg

Wed 7/10

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

1 stop9h 50m

C$ 399

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 22/10

12:45 p.m.-6:12 p.m.

1 stop6h 27m

Winnipeg

Sat 24/10

1:30 p.m.-9:27 p.m.

1 stop6h 57m

C$ 409

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 16/10

6:00 a.m.-12:37 p.m.

1 stop7h 37m

Winnipeg

Fri 23/10

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

1 stop16h 54m

C$ 413

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 15/9

4:55 p.m.-11:27 p.m.

1 stop7h 32m

Winnipeg

Sat 19/9

5:00 a.m.-11:51 a.m.

1 stop5h 51m

C$ 416

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 15/9

3:13 p.m.-10:33 p.m.

1 stop8h 20m

Winnipeg

Sat 19/9

1:30 p.m.-9:26 p.m.

2 stops6h 56m

C$ 418

Flights are sorted by cheapest round-trip flights 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$ 605 to C$ 844.
The lowest price recently found on this route was C$ 362.

What is the cheapest month to fly to Winnipeg?

The cheapest month to fly to Winnipeg from Boston is in August. Flight prices, which tend to average around C$ 603, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of August, then departing from Boston during the month May is also very affordable. Most momondo users find prices during this month for around C$ 714.

Can stopping save me money on Boston to Winnipeg flights?

You could potentially save up to 20% 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 September 2026, prices for Boston to Winnipeg flights are approximately 19% 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$ 168

Fastest flight time

5h 55m

Direct flights

None
The best one-way flight to Winnipeg from Boston in the past 72 hours is C$ 168. The best round-trip flight deal from Boston to Winnipeg found on momondo in the last 72 hours is C$ 362.
The fastest flight from Boston to Winnipeg takes 5h 55m
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 55m 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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