Cheap flights from Boston to Winnipeg from C$ 165

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 28/9. 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

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

Find the cheapest flights from Boston to Winnipeg

Cheap round-trip flights

 Logo
6:30 p.m. - 11:41 a.m.BOS-YWG
18h 11m1 stop
 Logo
7:30 a.m. - 10:48 a.m.YWG-BOS
26h 18m1 stop
C$ 364
Find Deal
Fri, 24 Oct - Fri, 31 Oct
 Logo
8:24 p.m. - 4:22 p.m.BOS-YWG
20h 58m2 stops
 Logo
6:30 a.m. - 5:40 p.m.YWG-BOS
10h 10m1 stop
C$ 388
Find Deal
Thu, 16 Oct - Mon, 20 Oct
Air Canada Logo
10:40 a.m. - 11:25 p.m.BOS-YWG
13h 45m1 stop
Air Canada Logo
5:00 a.m. - 11:29 a.m.YWG-BOS
5h 29m1 stop
C$ 429Air Canada
Find Deal
Wed, 1 Oct - Wed, 8 Oct
WestJet Logo
6:30 p.m. - 9:25 p.m.BOS-YWG
27h 55m2 stops
WestJet Logo
12:15 p.m. - 6:10 p.m.YWG-BOS
28h 55m2 stops
C$ 453WestJet
Find Deal
Thu, 2 Oct - Sun, 5 Oct
United Airlines Logo
6:00 a.m. - 3:31 p.m.BOS-YWG
10h 31m2 stops
United Airlines Logo
2:20 p.m. - 11:59 p.m.YWG-BOS
8h 39m2 stops
C$ 469United Airlines
Find Deal
Wed, 1 Oct - Wed, 8 Oct
Air Canada Logo
10:40 a.m. - 4:15 p.m.BOS-YWG
6h 35m1 stop
Air Canada Logo
8:15 a.m. - 2:52 p.m.YWG-BOS
5h 37m1 stop
C$ 476Air Canada
Find Deal
Sat, 25 Oct - Sun, 2 Nov
United Airlines Logo
8:00 a.m. - 10:33 p.m.BOS-YWG
15h 33m1 stop
United Airlines Logo
8:40 a.m. - 11:39 p.m.YWG-BOS
13h 59m1 stop
C$ 487United Airlines
Find Deal
Thu, 23 Oct - Mon, 3 Nov
WestJet Logo
7:00 p.m. - 5:25 p.m.BOS-YWG
23h 25m2 stops
WestJet Logo
6:15 p.m. - 6:10 p.m.YWG-BOS
22h 55m2 stops
C$ 550WestJet
Find Deal
Fri, 26 Sep - Thu, 2 Oct
Delta Logo
10:30 a.m. - 11:27 p.m.BOS-YWG
13h 57m2 stops
Delta Logo
5:40 p.m. - 11:59 p.m.YWG-BOS
5h 19m1 stop
C$ 590Delta
Find Deal
Wed, 29 Oct - Fri, 31 Oct
Delta Logo
10:00 a.m. - 11:27 p.m.BOS-YWG
14h 27m2 stops
Delta Logo
12:20 p.m. - 1:13 a.m.YWG-BOS
11h 53m2 stops
C$ 598Delta
Find Deal
Wed, 29 Oct - Mon, 3 Nov

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets
Air Canada
1 Oct
BOS10:40 a.m.Boston Logan Intl
13h 45m
1 stop
YWG11:25 p.m.Winnipeg
8 Oct
YWG5:00 a.m.Winnipeg
5h 29m
1 stop
BOS11:29 a.m.Boston Logan Intl
Air Canada
25 Oct
BOS10:40 a.m.Boston Logan Intl
6h 35m
1 stop
YWG4:15 p.m.Winnipeg
2 Nov
YWG8:15 a.m.Winnipeg
5h 37m
1 stop
BOS2:52 p.m.Boston Logan Intl
Air Canada
28 Oct
BOS5:30 a.m.Boston Logan Intl
5h 46m
1 stop
YWG10:16 a.m.Winnipeg
4 Nov
YWG8:15 a.m.Winnipeg
5h 37m
1 stop
BOS2:52 p.m.Boston Logan Intl

WestJet flights from Boston to Winnipeg

Our best WestJet deals on Boston to Winnipeg flight tickets
WestJet
2 Oct
BOS6:30 p.m.Boston Logan Intl
27h 55m
2 stops
YWG9:25 p.m.Winnipeg
5 Oct
YWG12:15 p.m.Winnipeg
28h 55m
2 stops
BOS6:10 p.m.Boston Logan Intl
WestJet
26 Sep
BOS7:00 p.m.Boston Logan Intl
23h 25m
2 stops
YWG5:25 p.m.Winnipeg
2 Oct
YWG6:15 p.m.Winnipeg
22h 55m
2 stops
BOS6:10 p.m.Boston Logan Intl
WestJet
2 Oct
BOS6:30 p.m.Boston Logan Intl
20h 55m
2 stops
YWG2:25 p.m.Winnipeg
5 Oct
YWG5:30 p.m.Winnipeg
23h 40m
3 stops
BOS6:10 p.m.Boston Logan Intl

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 15 September 2025.
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

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 24/10

6:30 p.m.-11:41 a.m.

1 stop18h 11m

Winnipeg

Fri 31/10

7:30 a.m.-10:48 a.m.

1 stop26h 18m

C$ 364

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 16/10

8:24 p.m.-4:22 p.m.

2 stops20h 58m

Winnipeg

Mon 20/10

6:30 a.m.-5:40 p.m.

1 stop10h 10m

C$ 388

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 1/10

10:40 a.m.-11:25 p.m.

1 stop13h 45m

Winnipeg

Wed 8/10

5:00 a.m.-11:29 a.m.

1 stop5h 29m

C$ 429

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 2/10

6:30 p.m.-9:25 p.m.

2 stops27h 55m

Winnipeg

Sun 5/10

12:15 p.m.-6:10 p.m.

2 stops28h 55m

C$ 453

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 1/10

6:00 a.m.-3:31 p.m.

2 stops10h 31m

Winnipeg

Wed 8/10

2:20 p.m.-11:59 p.m.

2 stops8h 39m

C$ 469

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 25/10

10:40 a.m.-4:15 p.m.

1 stop6h 35m

Winnipeg

Sun 2/11

8:15 a.m.-2:52 p.m.

1 stop5h 37m

C$ 476

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 23/10

8:00 a.m.-10:33 p.m.

1 stop15h 33m

Winnipeg

Mon 3/11

8:40 a.m.-11:39 p.m.

1 stop13h 59m

C$ 487

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 26/9

7:00 p.m.-5:25 p.m.

2 stops23h 25m

Winnipeg

Thu 2/10

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

2 stops22h 55m

C$ 550

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 29/10

10:30 a.m.-11:27 p.m.

2 stops13h 57m

Winnipeg

Fri 31/10

5:40 p.m.-11:59 p.m.

1 stop5h 19m

C$ 590

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 29/10

10:00 a.m.-11:27 p.m.

2 stops14h 27m

Winnipeg

Mon 3/11

12:20 p.m.-1:13 a.m.

2 stops11h 53m

C$ 598

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 cheapest month to fly to Winnipeg?

The cheapest month to fly to Winnipeg from Boston is in July. Flight prices, which tend to average around C$ 322, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of July, then departing from Boston during the month January is also very affordable. Most momondo users find prices during this month for around C$ 472.

What is the cheapest day to depart on your flight to Winnipeg?

Our data shows that Wednesday is the least expensive day to fly to Winnipeg. Tickets to fly out on this day can be as low as C$ 622. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Thursday is C$ 837.

How far in advance should I book a flight 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$ 608 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$ 400 on momondo.

How have Boston to Winnipeg flight prices changed over time?

As of September 2025, prices for Boston to Winnipeg flights are approximately 9% 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

Direct flights

None
There are no direct flights from Boston to Winnipeg. There are no popular flight routes 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 46m 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
Selkirk
Morden
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 15/10
Wed 22/10

Find better results for your trip to Canada