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Cheap flights from Boston to Winnipeg from £94

BOS — YWG
24 Oct — 31 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 6/1006:00 -
1 stop7h 37m
Fri 16/1008:45 -
1 stop14h 14m
Deal found 22/9£228
Wed 7/1020:30 -
1 stop17h 07m
Wed 14/1005:00 -
2 stops8h 41m
Deal found 22/9£233
Sat 10/1015:15 -
1 stop9h 04m
Fri 16/1012:38 -
1 stop8h 41m
Deal found 22/9£241
Sat 3/1006:00 -
1 stop7h 37m
Sun 11/1008:10 -
1 stop5h 31m
Deal found 19/9£249
Wed 4/1109:20 -
1 stop12h 37m
Thu 12/1114:15 -
1 stop8h 20m
Deal found 20/9£254
Tue 13/1007:01 -
1 stop16h 32m
Thu 15/1005:00 -
2 stops8h 41m
Deal found 21/9£259
Sun 1/1106:00 -
1 stop7h 23m
Tue 10/1114:15 -
2 stops8h 44m
Deal found 20/9£261
Wed 4/1113:15 -
1 stop5h 55m
Thu 12/1111:40 -
2 stops8h 52m
Deal found 20/9£269
Wed 7/1015:15 -
1 stop9h 04m
Fri 16/1012:38 -
1 stop8h 41m
Deal found 22/9£271
Thu 5/1108:00 -
2 stops11h 10m
Wed 11/1111:40 -
2 stops8h 52m
Deal found 20/9£273

Find flight deals from Boston to Winnipeg

Round-trip from

£228

One-way from

£94

Popular in

February

Cheapest in

September

Average price

£274
United Airlines
  • United Airlines
  • 6/10-16/10
  • 2 total stops
  • 21h 51m total
  • Boston to Winnipeg
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United Airlines
  • United Airlines
  • 7/10-31/12
  • 1 total stop
  • 17h 07m total
  • Boston to Winnipeg
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (£98 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (£17 potential savings vs. average return price).
Search Deals
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

Wed 7/10

20:30-12:37

1 stop17h 07m

Winnipeg

Wed 31/12

00:00-01:00

Nonstop0h 00m

£94
Fastest return journey

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 10/10

15:15-23:19

1 stop9h 04m

Winnipeg

Wed 31/12

00:00-01:00

Nonstop0h 00m

£107

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 5/10

19:00-12:37

2 stops18h 37m

Winnipeg

Wed 31/12

00:00-01:00

Nonstop0h 00m

£111

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 10/10

20:25-20:57

2 stops25h 32m

Winnipeg

Wed 31/12

00:00-01:00

Nonstop0h 00m

£115

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 19/10

20:25-12:37

2 stops17h 12m

Winnipeg

Wed 31/12

00:00-01:00

Nonstop0h 00m

£115

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 5/10

08:15-16:54

1 stop9h 39m

Winnipeg

Wed 31/12

00:00-01:00

Nonstop0h 00m

£134

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 7/10

20:30-12:37

1 stop17h 07m

Winnipeg

Wed 14/10

05:00-14:41

2 stops8h 41m

£233

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 9/10

15:15-23:19

1 stop9h 04m

Winnipeg

Wed 31/12

00:00-01:00

Nonstop0h 00m

£242

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 3/11

07:15-20:57

1 stop14h 42m

Winnipeg

Thu 12/11

14:15-00:46

1 stop9h 31m

£254

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 4/11

07:27-11:48

1 stop5h 21m

Winnipeg

Mon 9/11

17:32-23:44

1 stop5h 12m

£254

Flights are sorted by cheapest return flights first.

Deals found on 22/9

Showing 1-10 of 17 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, September is the cheapest month in which you can book a flight from Boston to Winnipeg (average of £274). Flying from Boston to Winnipeg in February is currently the most expensive (average of £691). 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.

How much does it cost for a return flight from Boston to Winnipeg?

Airfare is below average for this route at the moment.

Boston to Winnipeg flights typically cost between £240 and £431 in October.
The cheapest return price found within the last 5 days was £228 on United Airlines (6 Oct–16 Oct).

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 5h 21m. 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, September is the cheapest month in which you can book a flight from Boston to Winnipeg (average of £274). Flying from Boston to Winnipeg in February is currently the most expensive (average of £691). 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.

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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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