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Cheap flights from Boston to Winnipeg from C$ 210

BOS — YWG
22 Nov — 29 Nov1
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

Sat 5/125:30 a.m. -
1 stop5h 45m
Sat 12/129:05 a.m. -
1 stop5h 48m
Deal found 21/10C$ 426
Thu 3/125:30 a.m. -
1 stop5h 45m
Mon 7/129:05 a.m. -
1 stop5h 48m
Deal found 20/10C$ 498
Tue 8/121:15 p.m. -
1 stop5h 59m
Sat 12/1211:00 a.m. -
2 stops29h 46m
Deal found 20/10C$ 503
Thu 3/128:27 a.m. -
2 stops13h 28m
Mon 7/123:15 p.m. -
1 stop6h 38m
Deal found 21/10C$ 517
Thu 3/128:00 a.m. -
2 stops11h 14m
Mon 7/1212:40 p.m. -
2 stops8h 59m
Deal found 20/10C$ 544
Wed 16/126:00 a.m. -
1 stop7h 23m
Wed 30/123:15 p.m. -
2 stops8h 44m
Deal found 22/10C$ 551

Find flight deals from Boston to Winnipeg

Round-trip from

C$ 426

One-way from

C$ 210

Popular in

January

Cheapest in

September

Average price

C$ 513
Air Canada
  • Air Canada
  • 5/12-12/12
  • 2 total stops
  • 11h 33m total
  • Boston to Winnipeg
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Porter Airlines
  • Porter Airlines
  • 3/12-31/12
  • 1 total stop
  • 5h 59m total
  • Boston to Winnipeg
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Highest demand for flights based on searches. 8% potential increase in price (C$ 105 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 42 potential savings vs. average RT price).
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Average for round-trip flights in October 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.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 3/12

1:15 p.m.-7:14 p.m.

1 stop5h 59m

Winnipeg

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 210

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 3/2

10:25 a.m.-5:38 p.m.

1 stop7h 13m

Winnipeg

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 238

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 3/12

1:15 p.m.-1:44 a.m.

2 stops12h 29m

Winnipeg

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 377

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 4/2

1:15 p.m.-7:10 p.m.

1 stop5h 55m

Winnipeg

Tue 9/2

11:40 a.m.-9:42 p.m.

2 stops10h 02m

C$ 428

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 1/3

1:15 p.m.-7:10 p.m.

1 stop5h 55m

Winnipeg

Tue 9/3

11:40 a.m.-9:42 p.m.

2 stops10h 02m

C$ 442

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 2/3

1:15 p.m.-7:10 p.m.

1 stop5h 55m

Winnipeg

Fri 5/3

11:40 a.m.-9:42 p.m.

2 stops10h 02m

C$ 478

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 2/3

10:25 a.m.-5:37 p.m.

1 stop7h 12m

Winnipeg

Fri 5/3

3:45 p.m.-10:35 p.m.

1 stop6h 50m

C$ 505

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 8/12

8:27 a.m.-9:55 p.m.

2 stops13h 28m

Winnipeg

Sat 12/12

3:05 p.m.-9:28 p.m.

1 stop6h 23m

C$ 508

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 3/12

5:30 a.m.-11:15 a.m.

1 stop5h 45m

Winnipeg

Mon 7/12

6:15 a.m.-2:53 p.m.

2 stops8h 38m

C$ 516

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 5/12

8:27 a.m.-9:55 p.m.

2 stops13h 28m

Winnipeg

Sat 12/12

3:15 p.m.-9:53 p.m.

1 stop6h 38m

C$ 517

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/10

Showing 1-10 of 15 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 round-trip 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 C$ 510). Flying from Boston to Winnipeg in January is currently the most expensive (average of C$ 1,088). 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 to fly round-trip from Boston to Winnipeg?

Airfare is below average for this route at the moment.

Boston to Winnipeg flights typically cost between C$ 492 and C$ 858 in December.
The cheapest round-trip price found within the last 5 days was C$ 426 on Air Canada (5 Dec-12 Dec).

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 55m. Fly via Porter Airlines or Air Canada to get the fastest option. Boston and Winnipeg are separated by a distance of 2173 km. Both multi-stop and direct flights can be found to your destination and back.

  • 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 vacation 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 C$ 510). Flying from Boston to Winnipeg in January is currently the most expensive (average of C$ 1,088). 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

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk

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Alternative routes for Boston to Winnipeg

Hartford to Winnipeg flights

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

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Winnipeg from Boston.

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

Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston to Winnipeg flexibly with Cheapflights today.

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

Yes! Start tracking prices for Boston to Winnipeg flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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