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Cheap flights from Boston to Winnipeg from C$ 187

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 31/3. 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.
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 a.m. - 5:35 p.m.
YWG
-
BOS
7h 15m
1 stop
C$ 355Porter Airlines
Wed, 27 May - Tue, 2 Jun
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 a.m. - 5:35 p.m.
YWG
-
BOS
7h 15m
1 stop
C$ 391Porter Airlines
Sat, 6 Jun - Mon, 8 Jun
Porter Airlines Logo
10:05 a.m. - 5:58 p.m.
BOS
-
YWG
8h 53m
2 stops
Porter Airlines Logo
9:20 a.m. - 5:35 p.m.
YWG
-
BOS
7h 15m
1 stop
C$ 393Porter Airlines
Wed, 27 May - Tue, 2 Jun
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$ 400Porter Airlines
Mon, 15 Jun - Fri, 19 Jun
Porter Airlines Logo
10:05 a.m. - 3:19 p.m.
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 a.m. - 5:35 p.m.
YWG
-
BOS
7h 15m
1 stop
C$ 407Porter Airlines
Mon, 15 Jun - Fri, 19 Jun
Porter Airlines Logo
10:05 a.m. - 5:58 p.m.
BOS
-
YWG
8h 53m
2 stops
Porter Airlines Logo
9:20 a.m. - 8:55 p.m.
YWG
-
BOS
10h 35m
2 stops
C$ 415Porter Airlines
Wed, 27 May - Tue, 2 Jun
United Airlines Logo
6:00 a.m. - 11:52 a.m.
BOS
-
YWG
6h 52m
1 stop
United Airlines Logo
2:00 p.m. - 12:59 a.m.
YWG
-
BOS
9h 59m
1 stop
C$ 423United Airlines
Sun, 3 May - Sat, 9 May
Air Canada Logo
5:10 a.m. - 10:03 a.m.
BOS
-
YWG
5h 53m
1 stop
Air Canada Logo
2:00 p.m. - 10:39 p.m.
YWG
-
BOS
7h 39m
1 stop
C$ 441Air Canada
Sun, 24 May - Sat, 30 May
Air Canada Logo
5:30 a.m. - 10:09 a.m.
BOS
-
YWG
5h 39m
1 stop
Air Canada Logo
3:15 p.m. - 10:39 p.m.
YWG
-
BOS
6h 24m
1 stop
C$ 443Air Canada
Thu, 30 Apr - Sat, 2 May
Air Canada Logo
5:10 a.m. - 11:08 a.m.
BOS
-
YWG
6h 58m
1 stop
Air Canada Logo
5:10 a.m. - 2:47 p.m.
YWG
-
BOS
8h 37m
2 stops
C$ 453Air Canada
Sun, 24 May - Sat, 30 May

Porter Airlines flights from Boston to Winnipeg

Our best Porter Airlines deals on Boston to Winnipeg flight tickets
Porter Airlines
27 May
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
2 Jun
YWG9:20 a.m.Winnipeg
7h 15m
1 stop
BOS5:35 p.m.Boston Logan Intl
C$ 355
Porter Airlines
6 Jun
BOS10:05 a.m.Boston Logan Intl
6h 14m
1 stop
YWG3:19 p.m.Winnipeg
8 Jun
YWG9:20 a.m.Winnipeg
7h 15m
1 stop
BOS5:35 p.m.Boston Logan Intl
C$ 391
Porter Airlines
27 May
BOS10:05 a.m.Boston Logan Intl
8h 53m
2 stops
YWG5:58 p.m.Winnipeg
2 Jun
YWG9:20 a.m.Winnipeg
7h 15m
1 stop
BOS5:35 p.m.Boston Logan Intl
C$ 393

United Airlines flights from Boston to Winnipeg

Our best United Airlines deals on Boston to Winnipeg flight tickets
United Airlines
3 May
BOS6:00 a.m.Boston Logan Intl
6h 52m
1 stop
YWG11:52 a.m.Winnipeg
9 May
YWG2:00 p.m.Winnipeg
9h 59m
1 stop
BOS12:59 a.m.Boston Logan Intl
C$ 423
United Airlines
24 Mar
BOS6:00 a.m.Boston Logan Intl
6h 57m
1 stop
YWG11:57 a.m.Winnipeg
25 Mar
YWG2:20 p.m.Winnipeg
18h 36m
2 stops
BOS9:56 a.m.Boston Logan Intl
C$ 765
United Airlines
24 Mar
BOS6:00 a.m.Boston Logan Intl
6h 57m
1 stop
YWG11:57 a.m.Winnipeg
25 Mar
YWG2:20 p.m.Winnipeg
18h 36m
2 stops
BOS9:56 a.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 6 March 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

Wed 27/5

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

1 stop6h 14m

Winnipeg

Tue 2/6

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

1 stop7h 15m

C$ 355

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 6/6

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

1 stop6h 14m

Winnipeg

Mon 8/6

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

1 stop7h 15m

C$ 391

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 27/5

10:05 a.m.-5:58 p.m.

2 stops8h 53m

Winnipeg

Tue 2/6

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

1 stop7h 15m

C$ 393

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 15/6

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

2 stops11h 48m

Winnipeg

Fri 19/6

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

1 stop7h 15m

C$ 400

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 15/6

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

1 stop6h 14m

Winnipeg

Fri 19/6

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

1 stop7h 15m

C$ 407

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 27/5

10:05 a.m.-5:58 p.m.

2 stops8h 53m

Winnipeg

Tue 2/6

9:20 a.m.-8:55 p.m.

2 stops10h 35m

C$ 415

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 3/5

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

1 stop6h 52m

Winnipeg

Sat 9/5

2:00 p.m.-12:59 a.m.

1 stop9h 59m

C$ 423

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 24/5

5:10 a.m.-10:03 a.m.

1 stop5h 53m

Winnipeg

Sat 30/5

2:00 p.m.-10:39 p.m.

1 stop7h 39m

C$ 441
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 30/4

5:30 a.m.-10:09 a.m.

1 stop5h 39m

Winnipeg

Sat 2/5

3:15 p.m.-10:39 p.m.

1 stop6h 24m

C$ 443

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 24/5

5:10 a.m.-11:08 a.m.

1 stop6h 58m

Winnipeg

Sat 30/5

5:10 a.m.-2:47 p.m.

2 stops8h 37m

C$ 453

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 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$ 356, 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 July is also very affordable. Most momondo users find prices during this month for around C$ 402.

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$ 674 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$ 412 on momondo.

Can stopping save me money on Boston to Winnipeg flights?

You could potentially save up to 44% 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 March 2026, prices for Boston to Winnipeg flights are approximately 14% 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

6h 11m

Direct flights

None
The fastest flight from Boston to Winnipeg takes 6h 11m
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. 6h 11m 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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