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Cheap flights from Boston to Winnipeg from C$ 512

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Winnipeg departing on 6/3. 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.
Multiple Airlines Logo
6:00 a.m. - 3:09 p.m.
BOS
-
YWG
10h 09m
1 stop
Multiple Airlines Logo
8:00 a.m. - 5:15 p.m.
YWG
-
BOS
32h 15m
1 stop
C$ 512Multiple Airlines
Fri, 6 Mar - Mon, 9 Mar
Multiple Airlines Logo
5:40 a.m. - 12:55 a.m.
BOS
-
YWG
20h 15m
2 stops
Multiple Airlines Logo
9:05 p.m. - 4:58 p.m.
YWG
-
BOS
18h 53m
3 stops
C$ 519Multiple Airlines
Thu, 14 May - Mon, 18 May
Multiple Airlines Logo
5:40 a.m. - 3:25 p.m.
BOS
-
YWG
34h 45m
3 stops
Multiple Airlines Logo
9:05 p.m. - 4:58 p.m.
YWG
-
BOS
18h 53m
3 stops
C$ 534Multiple Airlines
Thu, 14 May - Mon, 18 May
Multiple Airlines Logo
7:15 a.m. - 5:15 p.m.
BOS
-
YWG
11h 00m
1 stop
Multiple Airlines Logo
9:05 p.m. - 12:05 p.m.
YWG
-
BOS
14h 00m
2 stops
C$ 538Multiple Airlines
Thu, 14 May - Mon, 18 May
Multiple Airlines Logo
7:15 a.m. - 5:15 p.m.
BOS
-
YWG
11h 00m
1 stop
Multiple Airlines Logo
9:05 p.m. - 12:05 p.m.
YWG
-
BOS
14h 00m
2 stops
C$ 545Multiple Airlines
Thu, 14 May - Mon, 18 May
Air Canada Logo
5:30 a.m. - 10:15 a.m.
BOS
-
YWG
5h 45m
1 stop
Air Canada Logo
1:30 p.m. - 10:37 p.m.
YWG
-
BOS
8h 07m
1 stop
C$ 553Air Canada
Thu, 26 Feb - Thu, 26 Feb
Multiple Airlines Logo
6:00 a.m. - 3:09 p.m.
BOS
-
YWG
10h 09m
1 stop
Multiple Airlines Logo
8:00 a.m. - 11:41 a.m.
YWG
-
BOS
26h 41m
2 stops
C$ 555Multiple Airlines
Fri, 6 Mar - Mon, 9 Mar
Multiple Airlines Logo
6:35 p.m. - 9:45 a.m.
BOS
-
YWG
16h 10m
1 stop
Multiple Airlines Logo
6:00 a.m. - 3:50 p.m.
YWG
-
BOS
8h 50m
1 stop
C$ 565Multiple Airlines
Thu, 14 May - Mon, 18 May
Multiple Airlines Logo
10:05 a.m. - 4:25 p.m.
BOS
-
YWG
7h 20m
1 stop
Multiple Airlines Logo
6:00 a.m. - 3:50 p.m.
YWG
-
BOS
8h 50m
1 stop
C$ 575Multiple Airlines
Fri, 22 May - Sat, 30 May
Multiple Airlines Logo
5:40 a.m. - 12:55 a.m.
BOS
-
YWG
20h 15m
2 stops
Multiple Airlines Logo
6:15 a.m. - 11:59 p.m.
YWG
-
BOS
16h 44m
2 stops
C$ 582Multiple Airlines
Thu, 14 May - Mon, 18 May

Air Canada flights from Boston to Winnipeg

Our best Air Canada deals on Boston to Winnipeg flight tickets
Air Canada
26 Feb
BOS5:30 a.m.Boston Logan Intl
5h 45m
1 stop
YWG10:15 a.m.Winnipeg
26 Feb
YWG1:30 p.m.Winnipeg
8h 07m
1 stop
BOS10:37 p.m.Boston Logan Intl
C$ 553
Air Canada
6 Mar
BOS5:30 a.m.Boston Logan Intl
5h 45m
1 stop
YWG10:15 a.m.Winnipeg
9 Mar
YWG8:15 a.m.Winnipeg
5h 37m
1 stop
BOS2:52 p.m.Boston Logan Intl
C$ 708
Air Canada
6 Mar
BOS6:15 a.m.Boston Logan Intl
7h 24m
1 stop
YWG12:39 p.m.Winnipeg
9 Mar
YWG8:15 a.m.Winnipeg
5h 37m
1 stop
BOS2:52 p.m.Boston Logan Intl
C$ 714

Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets
Porter Airlines
14 Jun
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
20 Jun
YWG9:20 a.m.Winnipeg
7h 15m
1 stop
BOS5:35 p.m.Boston Logan Intl
C$ 675
Porter Airlines
6 Mar
BOS3:30 p.m.Boston Logan Intl
9h 05m
2 stops
YWG11:35 p.m.Winnipeg
9 Mar
YWG6:00 a.m.Winnipeg
12h 16m
2 stops
BOS7:16 p.m.Boston Logan Intl
C$ 818
Porter Airlines
1 Jul
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
7 Jul
YWG9:20 a.m.Winnipeg
7h 15m
1 stop
BOS5:35 p.m.Boston Logan Intl
C$ 822

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 4 February 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

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 6/3

6:00 a.m.-3:09 p.m.

1 stop10h 09m

Winnipeg

Mon 9/3

8:00 a.m.-5:15 p.m.

1 stop32h 15m

C$ 512

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 14/5

5:40 a.m.-12:55 a.m.

2 stops20h 15m

Winnipeg

Mon 18/5

9:05 p.m.-4:58 p.m.

3 stops18h 53m

C$ 519

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 14/5

5:40 a.m.-3:25 p.m.

3 stops34h 45m

Winnipeg

Mon 18/5

9:05 p.m.-4:58 p.m.

3 stops18h 53m

C$ 534

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 14/5

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

1 stop11h 00m

Winnipeg

Mon 18/5

9:05 p.m.-12:05 p.m.

2 stops14h 00m

C$ 538

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 14/5

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

1 stop11h 00m

Winnipeg

Mon 18/5

9:05 p.m.-12:05 p.m.

2 stops14h 00m

C$ 545

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 26/2

5:30 a.m.-10:15 a.m.

1 stop5h 45m

Winnipeg

Thu 26/2

1:30 p.m.-10:37 p.m.

1 stop8h 07m

C$ 553

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 6/3

6:00 a.m.-3:09 p.m.

1 stop10h 09m

Winnipeg

Mon 9/3

8:00 a.m.-11:41 a.m.

2 stops26h 41m

C$ 555

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 14/5

6:35 p.m.-9:45 a.m.

1 stop16h 10m

Winnipeg

Mon 18/5

6:00 a.m.-3:50 p.m.

1 stop8h 50m

C$ 565

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 22/5

10:05 a.m.-4:25 p.m.

1 stop7h 20m

Winnipeg

Sat 30/5

6:00 a.m.-3:50 p.m.

1 stop8h 50m

C$ 575

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 14/5

5:40 a.m.-12:55 a.m.

2 stops20h 15m

Winnipeg

Mon 18/5

6:15 a.m.-11:59 p.m.

2 stops16h 44m

C$ 582

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 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$ 318, 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 March is also very affordable. Most momondo users find prices during this month for around C$ 429.

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$ 598 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$ 272 on momondo.

Can stopping save me money on Boston to Winnipeg flights?

You could potentially save up to 1% 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 February 2026, prices for Boston to Winnipeg flights are approximately 12% 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 45m

Direct flights

None
The fastest flight from Boston to Winnipeg takes 5h 45m
There are no direct flights from Boston to Winnipeg. There are no popular flight routes from Boston to Winnipeg.
Search flight deals

  • 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 45m 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

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.
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