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Cheap flights from Boston to Winnipeg from C$ 241

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 15/7. 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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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
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 a.m. - 7:15 p.m.
YWG
-
BOS
8h 55m
1 stop
C$ 462Porter Airlines
Thu, 17 Sep - Tue, 29 Sep
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 a.m. - 7:15 p.m.
YWG
-
BOS
8h 55m
1 stop
C$ 486Porter Airlines
Thu, 15 Oct - Wed, 21 Oct
Porter Airlines Logo
7:10 a.m. - 5:58 p.m.
BOS
-
YWG
11h 48m
2 stops
Porter Airlines Logo
9:20 a.m. - 7:15 p.m.
YWG
-
BOS
8h 55m
1 stop
C$ 490Porter Airlines
Thu, 17 Sep - Tue, 29 Sep
Air Canada Logo
10:40 a.m. - 3:09 p.m.
BOS
-
YWG
5h 29m
1 stop
Air Canada Logo
5:10 a.m. - 11:55 a.m.
YWG
-
BOS
5h 45m
1 stop
C$ 497Air Canada
Thu, 17 Sep - Sat, 19 Sep
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
12:15 p.m. - 7:15 p.m.
YWG
-
BOS
6h 00m
1 stop
C$ 501Porter Airlines
Thu, 13 Aug - Sat, 15 Aug
Air Canada Logo
6:00 a.m. - 11:15 a.m.
BOS
-
YWG
6h 15m
1 stop
Air Canada Logo
3:20 p.m. - 10:40 p.m.
YWG
-
BOS
6h 20m
1 stop
C$ 503Air Canada
Fri, 4 Sep - Tue, 8 Sep
Air Canada Logo
10:40 a.m. - 3:09 p.m.
BOS
-
YWG
5h 29m
1 stop
Air Canada Logo
5:10 a.m. - 2:41 p.m.
YWG
-
BOS
8h 31m
2 stops
C$ 509Air Canada
Thu, 17 Sep - Sat, 19 Sep
Porter Airlines Logo
7:10 a.m. - 5:58 p.m.
BOS
-
YWG
11h 48m
2 stops
Porter Airlines Logo
9:20 a.m. - 5:35 p.m.
YWG
-
BOS
7h 15m
1 stop
C$ 510Porter Airlines
Sat, 11 Jul - Tue, 14 Jul
United Airlines Logo
6:00 a.m. - 11:52 a.m.
BOS
-
YWG
6h 52m
1 stop
United Airlines Logo
7:00 a.m. - 11:59 p.m.
YWG
-
BOS
15h 59m
2 stops
C$ 514United Airlines
Sun, 6 Sep - Sat, 12 Sep
Air Canada Logo
5:50 a.m. - 2:22 p.m.
BOS
-
YWG
9h 32m
2 stops
Air Canada Logo
5:10 a.m. - 2:41 p.m.
YWG
-
BOS
8h 31m
2 stops
C$ 527Air Canada
Thu, 17 Sep - Sat, 19 Sep

Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets
Porter Airlines
17 Sep
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
29 Sep
YWG9:20 a.m.Winnipeg
8h 55m
1 stop
BOS7:15 p.m.Boston Logan Intl
C$ 462
Porter Airlines
15 Oct
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
21 Oct
YWG9:20 a.m.Winnipeg
8h 55m
1 stop
BOS7:15 p.m.Boston Logan Intl
C$ 486
Porter Airlines
17 Sep
BOS7:10 a.m.Boston Logan Intl
11h 48m
2 stops
YWG5:58 p.m.Winnipeg
29 Sep
YWG9:20 a.m.Winnipeg
8h 55m
1 stop
BOS7:15 p.m.Boston Logan Intl
C$ 490

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets
Air Canada
17 Sep
BOS10:40 a.m.Boston Logan Intl
5h 29m
1 stop
YWG3:09 p.m.Winnipeg
19 Sep
YWG5:10 a.m.Winnipeg
5h 45m
1 stop
BOS11:55 a.m.Boston Logan Intl
C$ 497
Air Canada
4 Sep
BOS6:00 a.m.Boston Logan Intl
6h 15m
1 stop
YWG11:15 a.m.Winnipeg
8 Sep
YWG3:20 p.m.Winnipeg
6h 20m
1 stop
BOS10:40 p.m.Boston Logan Intl
C$ 503
Air Canada
17 Sep
BOS10:40 a.m.Boston Logan Intl
5h 29m
1 stop
YWG3:09 p.m.Winnipeg
19 Sep
YWG5:10 a.m.Winnipeg
8h 31m
2 stops
BOS2:41 p.m.Boston Logan Intl
C$ 509

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 21 May 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

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 17/9

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

1 stop6h 14m

Winnipeg

Tue 29/9

9:20 a.m.-7:15 p.m.

1 stop8h 55m

C$ 462

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 15/10

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

1 stop6h 14m

Winnipeg

Wed 21/10

9:20 a.m.-7:15 p.m.

1 stop8h 55m

C$ 486

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 17/9

7:10 a.m.-5:58 p.m.

2 stops11h 48m

Winnipeg

Tue 29/9

9:20 a.m.-7:15 p.m.

1 stop8h 55m

C$ 490
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 17/9

10:40 a.m.-3:09 p.m.

1 stop5h 29m

Winnipeg

Sat 19/9

5:10 a.m.-11:55 a.m.

1 stop5h 45m

C$ 497

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 13/8

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

1 stop6h 14m

Winnipeg

Sat 15/8

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

1 stop6h 00m

C$ 501

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 4/9

6:00 a.m.-11:15 a.m.

1 stop6h 15m

Winnipeg

Tue 8/9

3:20 p.m.-10:40 p.m.

1 stop6h 20m

C$ 503

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 17/9

10:40 a.m.-3:09 p.m.

1 stop5h 29m

Winnipeg

Sat 19/9

5:10 a.m.-2:41 p.m.

2 stops8h 31m

C$ 509

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 11/7

7:10 a.m.-5:58 p.m.

2 stops11h 48m

Winnipeg

Tue 14/7

9:20 a.m.-5:35 p.m.

1 stop7h 15m

C$ 510

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 6/9

6:00 a.m.-11:52 a.m.

1 stop6h 52m

Winnipeg

Sat 12/9

7:00 a.m.-11:59 p.m.

2 stops15h 59m

C$ 514

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 17/9

5:50 a.m.-2:22 p.m.

2 stops9h 32m

Winnipeg

Sat 19/9

5:10 a.m.-2:41 p.m.

2 stops8h 31m

C$ 527

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 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?

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$ 578, 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 September is also very affordable. Most momondo users find prices during this month for around C$ 596.

How far in advance should I book a flight from Boston to Winnipeg?

You are more likely to see cheaper flights to Winnipeg from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Winnipeg for around C$ 745 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Winnipeg from Boston for as low as C$ 503 on momondo.

Can stopping save me money on Boston to Winnipeg flights?

You could potentially save up to 11% 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 May 2026, prices for Boston to Winnipeg flights are approximately 151% 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

Fastest flight time

5h 29m

Direct flights

None
The fastest flight from Boston to Winnipeg takes 5h 29m
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 29m 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
Morden
Selkirk
Portage la Prairie

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.

An easier way to manage your Winnipeg trip

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