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Cheap flights from Boston to Winnipeg from C$ 209

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Winnipeg departing on 15/9. 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

Find the cheapest flights from Boston to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 14m1 stop Toronto Pearson Intl
Porter Airlines Logo
12:15 p.m. - 7:15 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 00m1 stop Toronto Pearson Intl
C$ 413Porter Airlines
Sat, 29 Aug - Sat, 5 Sep
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
7:00 a.m. - 5:40 p.m.YWG  Winnipeg-BOS Boston Logan Intl
9h 40m1 stop Calgary
C$ 424Multiple Airlines
Fri, 9 Oct - Sun, 11 Oct
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 14m1 stop Toronto Pearson Intl
Porter Airlines Logo
9:20 a.m. - 6:35 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 15m1 stop Toronto Pearson Intl
C$ 461Porter Airlines
Sat, 26 Sep - Wed, 30 Sep
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 14m1 stop Toronto Pearson Intl
Porter Airlines Logo
9:20 a.m. - 6:35 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 15m1 stop Toronto Pearson Intl
C$ 482Porter Airlines
Thu, 1 Oct - Mon, 5 Oct
WestJet Logo
6:30 p.m. - 12:15 p.m.BOS  Boston Logan Intl-YWG Winnipeg
18h 45m1 stop Calgary
WestJet Logo
6:00 a.m. - 5:40 p.m.YWG  Winnipeg-BOS Boston Logan Intl
10h 40m1 stop Calgary
C$ 485WestJet
Sat, 3 Oct - Tue, 13 Oct
Multiple Airlines Logo
7:00 a.m. - 4:25 p.m.BOS  Boston Logan Intl-YWG Winnipeg
10h 25m1 stop Toronto Island
Multiple Airlines Logo
11:15 a.m. - 10:30 a.m.YWG  Winnipeg-BOS Boston Logan Intl
22h 15m2 stops Montreal St Hubert Toronto Island
C$ 492Multiple Airlines
Thu, 3 Sep - Wed, 9 Sep
Multiple Airlines Logo
4:30 p.m. - 12:55 a.m.BOS  Boston Logan Intl-YWG Winnipeg
9h 25m1 stop Toronto Island
Multiple Airlines Logo
11:15 a.m. - 10:30 a.m.YWG  Winnipeg-BOS Boston Logan Intl
22h 15m2 stops Montreal St Hubert Toronto Pearson Intl
C$ 495Multiple Airlines
Thu, 10 Sep - Sun, 20 Sep
Multiple Airlines Logo
10:05 a.m. - 8:20 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 15m1 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$ 498Multiple Airlines
Sat, 19 Sep - Mon, 21 Sep
Multiple Airlines Logo
7:00 a.m. - 5:15 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 15m1 stop Toronto Island
Multiple Airlines Logo
6:15 a.m. - 5:25 p.m.YWG  Winnipeg-BOS Boston Logan Intl
10h 10m1 stop Toronto Pearson Intl
C$ 499Multiple Airlines
Thu, 10 Sep - Sun, 20 Sep
Multiple Airlines Logo
10:05 a.m. - 5:15 p.m.BOS  Boston Logan Intl-YWG Winnipeg
8h 10m1 stop Toronto Pearson Intl
Multiple Airlines Logo
11:15 a.m. - 10:30 a.m.YWG  Winnipeg-BOS Boston Logan Intl
22h 15m2 stops Montreal St Hubert Toronto Island
C$ 502Multiple Airlines
Thu, 17 Sep - Mon, 21 Sep

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WestJet flights from Boston to Winnipeg

Our best WestJet deals on Boston to Winnipeg flight tickets
WestJet
3 Oct
BOS6:30 p.m.Boston Logan Intl
18h 45m
1 stop
YWG12:15 p.m.Winnipeg
13 Oct
YWG6:00 a.m.Winnipeg
10h 40m
1 stop
BOS5:40 p.m.Boston Logan Intl
C$ 485
WestJet
1 Sep
BOS7:25 a.m.Boston Logan Intl
26h 55m
2 stops
YWG9:20 a.m.Winnipeg
5 Sep
YWG12:00 p.m.Winnipeg
9h 20m
1 stop
BOS10:20 p.m.Boston Logan Intl
C$ 534
WestJet
9 Oct
BOS6:30 p.m.Boston Logan Intl
21h 10m
2 stops
YWG2:40 p.m.Winnipeg
11 Oct
YWG8:30 p.m.Winnipeg
20h 10m
2 stops
BOS5:40 p.m.Boston Logan Intl
C$ 541

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets
Air Canada
2 Oct
BOS10:40 a.m.Boston Logan Intl
5h 29m
1 stop
YWG3:09 p.m.Winnipeg
4 Oct
YWG8:10 a.m.Winnipeg
5h 31m
1 stop
BOS2:41 p.m.Boston Logan Intl
C$ 609
Air Canada
3 Oct
BOS3:35 p.m.Boston Logan Intl
6h 39m
1 stop
YWG9:14 p.m.Winnipeg
11 Oct
YWG10:50 a.m.Winnipeg
6h 17m
1 stop
BOS6:07 p.m.Boston Logan Intl
C$ 613
Air Canada
28 Aug
BOS10:50 a.m.Boston Logan Intl
6h 30m
1 stop
YWG4:20 p.m.Winnipeg
30 Aug
YWG5:00 a.m.Winnipeg
5h 52m
1 stop
BOS11:52 a.m.Boston Logan Intl
C$ 1,004

momondo Fare Finder

 
Customize your flight search to find flights from Boston to Winnipeg 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 14 August 2026.
Use the filters below to find and compare flights from Boston to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 29/8

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

1 stop6h 14m

Winnipeg

Sat 5/9

12:15 p.m.-7:15 p.m.

1 stop6h 00m

C$ 413

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 9/10

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

1 stop6h 14m

Winnipeg

Sun 11/10

7:00 a.m.-5:40 p.m.

1 stop9h 40m

C$ 424

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 26/9

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

1 stop6h 14m

Winnipeg

Wed 30/9

9:20 a.m.-6:35 p.m.

1 stop8h 15m

C$ 461

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 1/10

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

1 stop6h 14m

Winnipeg

Mon 5/10

9:20 a.m.-6:35 p.m.

1 stop8h 15m

C$ 482

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 3/10

6:30 p.m.-12:15 p.m.

1 stop18h 45m

Winnipeg

Tue 13/10

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

1 stop10h 40m

C$ 485

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 3/9

7:00 a.m.-4:25 p.m.

1 stop10h 25m

Winnipeg

Wed 9/9

11:15 a.m.-10:30 a.m.

2 stops22h 15m

C$ 492

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 10/9

4:30 p.m.-12:55 a.m.

1 stop9h 25m

Winnipeg

Sun 20/9

11:15 a.m.-10:30 a.m.

2 stops22h 15m

C$ 495

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 19/9

10:05 a.m.-8:20 p.m.

1 stop11h 15m

Winnipeg

Mon 21/9

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

1 stop9h 50m

C$ 498

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 10/9

7:00 a.m.-5:15 p.m.

1 stop11h 15m

Winnipeg

Sun 20/9

6:15 a.m.-5:25 p.m.

1 stop10h 10m

C$ 499

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 17/9

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

1 stop8h 10m

Winnipeg

Mon 21/9

11:15 a.m.-10:30 a.m.

2 stops22h 15m

C$ 502

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$ 573 to C$ 954.
The lowest price recently found on this route was C$ 413.

What is the cheapest month to fly to Winnipeg?

The cheapest month to fly to Winnipeg from Boston is in May. Flight prices, which tend to average around C$ 721, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of May, then departing from Boston during the month October is also very affordable. Most momondo users find prices during this month for around C$ 724.

Can stopping save me money on Boston to Winnipeg flights?

You could potentially save up to 35% 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 August 2026, prices for Boston to Winnipeg flights are approximately 27% cheaper 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

Fastest flight time

5h 35m

Direct flights

None
The fastest flight from Boston to Winnipeg takes 5h 35m
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 35m 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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