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Cheap flights from Boston to Winnipeg from £95

BOS — YWG
11 Oct — 18 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Boston to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Boston to Winnipeg

Tue 13/1006:00 -
1 stop7h 37m
Fri 23/1005:00 -
1 stop5h 50m
Deal found 10/9£219
Tue 13/1020:30 -
1 stop17h 07m
Sat 17/1005:00 -
2 stops8h 41m
Deal found 8/9£228
Tue 13/1020:25 -
2 stops17h 12m
Fri 23/1014:00 -
1 stop9h 54m
Deal found 10/9£228
Fri 16/1007:01 -
1 stop16h 32m
Mon 19/1013:30 -
2 stops6h 56m
Deal found 8/9£234
Tue 13/1006:00 -
1 stop17h 33m
Sat 17/1014:00 -
1 stop8h 25m
Deal found 8/9£235
Tue 27/1006:00 -
1 stop7h 23m
Sat 31/1011:20 -
2 stops9h 08m
Deal found 10/9£240
Sat 26/914:15 -
2 stops9h 18m
Tue 29/905:00 -
1 stop5h 51m
Deal found 8/9£344
Thu 22/1010:05 -
1 stop6h 15m
Thu 29/1011:40 -
2 stops8h 52m
Deal found 7/9£385
Tue 15/907:20 -
2 stops14h 37m
Fri 18/914:00 -
1 stop8h 30m
Deal found 7/9£398
Sun 25/1008:00 -
2 stops11h 10m
Sun 1/1111:40 -
2 stops8h 52m
Deal found 10/9£413

Find flight deals from Boston to Winnipeg

Round-trip from

£219

One-way from

£95

Popular in

February

Cheapest in

August

Average price

£324
Air Canada
  • Air Canada
  • 13/10-23/10
  • 2 total stops
  • 13h 27m total
  • Boston to Winnipeg
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United Airlines
  • United Airlines
  • 22/9-31/12
  • 2 total stops
  • 11h 19m total
  • Boston to Winnipeg
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (£95 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (£17 potential savings vs. average return price).
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Average for round-trip flights in September 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Boston to Winnipeg that are best for you.

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Route

Depart

Return

Price

Cheapest return flight

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 22/9

10:38-20:57

2 stops11h 19m

Winnipeg

Wed 31/12

00:00-01:00

Nonstop0h 00m

£95
Fastest return journey

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sun 4/10

06:00-12:37

1 stop7h 37m

Winnipeg

Wed 31/12

00:00-01:00

Nonstop0h 00m

£95

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 13/10

20:25-12:37

2 stops17h 12m

Winnipeg

Fri 23/10

14:00-00:54

1 stop9h 54m

£228

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 16/10

07:01-22:33

1 stop16h 32m

Winnipeg

Mon 19/10

13:30-21:26

2 stops6h 56m

£234

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 27/10

06:00-12:23

1 stop7h 23m

Winnipeg

Sat 31/10

11:20-21:28

2 stops9h 08m

£240

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 1/3

15:00-23:34

1 stop9h 34m

Winnipeg

Tue 9/3

12:30-23:53

1 stop10h 23m

£344

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 26/9

14:15-22:33

2 stops9h 18m

Winnipeg

Tue 29/9

05:00-11:51

1 stop5h 51m

£344

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 22/10

10:05-15:20

1 stop6h 15m

Winnipeg

Thu 29/10

11:40-21:32

2 stops8h 52m

£385

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sun 25/10

08:00-18:10

2 stops11h 10m

Winnipeg

Sun 1/11

11:40-21:32

2 stops8h 52m

£413

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 22/10

06:00-12:37

1 stop7h 37m

Winnipeg

Thu 29/10

14:15-00:46

1 stop9h 31m

£417

Flights are sorted by cheapest return flights first.

Deals found on 8/9

Showing 1-10 of 13 resultsSorted by cheapest first
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Best time to book a flight from Boston to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Boston with our price prediction graph.
Estimated return price

Cheapflights Insights

Everything you need to know about your flight from Boston to Winnipeg

What is the cheapest month to book a flight from Boston to Winnipeg?

Currently, August is the cheapest month in which you can book a flight from Boston to Winnipeg (average of £323). Flying from Boston to Winnipeg in February is currently the most expensive (average of £678). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

  • How long is the flight from Boston to Winnipeg?

    There are many flights that can get you from Boston to Winnipeg in 9h 34m. Fly via United Airlines or Delta to get the fastest option. Boston and Winnipeg are separated by a distance of 1350 mi. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • Can I find deals for flights from Boston to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Boston to Winnipeg flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Boston to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Winnipeg.

  • Can I find deals for business class flights from Boston to Winnipeg?

    Yes. Cheapflights offers flight deals from Boston to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Boston to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Boston to Winnipeg (average of £323). Flying from Boston to Winnipeg in February is currently the most expensive (average of £678). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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How does Cheapflights help users find flights from Boston to Winnipeg?

When you search for this flight from Boston to Winnipeg, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Boston to Winnipeg?

Cheapflights helps you find that perfect flight to Winnipeg from Boston by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Boston to Winnipeg with no change fees?

Need flexible booking options for your flight to Winnipeg from Boston? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Boston to Winnipeg become cheaper?

Of course! You can now track prices for flights from Boston to Winnipeg and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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