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Cheap flights from Boston to Winnipeg from C$ 148

BOS — YWG
10 Oct — 17 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

Thu 22/1012:45 p.m. -
1 stop6h 27m
Sat 24/101:30 p.m. -
1 stop6h 57m
Deal found 8/9C$ 354
Sat 24/105:50 a.m. -
1 stop7h 39m
Sat 31/108:05 a.m. -
1 stop5h 48m
Deal found 9/9C$ 358
Sat 10/1012:45 p.m. -
1 stop6h 27m
Sat 17/103:20 p.m. -
1 stop6h 20m
Deal found 9/9C$ 361
Fri 16/107:00 a.m. -
2 stops11h 58m
Mon 19/106:00 a.m. -
1 stop10h 40m
Deal found 9/9C$ 376
Sat 10/1010:05 a.m. -
1 stop6h 15m
Fri 16/109:20 a.m. -
1 stop8h 15m
Deal found 5/9C$ 407
Sat 26/94:55 p.m. -
1 stop7h 32m
Tue 29/93:20 p.m. -
1 stop6h 20m
Deal found 8/9C$ 412
Sat 10/1010:05 a.m. -
1 stop6h 15m
Mon 12/109:05 p.m. -
1 stop19h 35m
Deal found 5/9C$ 416
Tue 13/108:30 p.m. -
1 stop17h 07m
Sat 17/105:00 a.m. -
2 stops8h 41m
Deal found 8/9C$ 425

Find flight deals from Boston to Winnipeg

Round-trip from

C$ 354

One-way from

C$ 148

Popular in

February

Cheapest in

August

Average price

C$ 604
Air Canada
  • Air Canada
  • 22/10-24/10
  • 2 total stops
  • 13h 24m total
  • Boston to Winnipeg
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Air Canada
  • Air Canada
  • 22/9-31/12
  • 1 total stop
  • 7h 32m total
  • Boston to Winnipeg
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 329 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 57 potential savings vs. average RT 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.

Fly from

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Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 22/9

4:55 p.m.-11:27 p.m.

1 stop7h 32m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 148

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 22/9

10:38 a.m.-8:57 p.m.

2 stops11h 19m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 176

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sun 4/10

6:00 a.m.-12:37 p.m.

1 stop7h 37m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 178

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sun 4/10

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

2 stops13h 05m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 248

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sun 4/10

6:30 p.m.-8:00 p.m.

3 stops26h 30m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 288
Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 19/12

1:15 p.m.-6:10 p.m.

1 stop5h 55m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 342

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 24/10

5:50 a.m.-12:29 p.m.

1 stop7h 39m

Winnipeg

Sat 31/10

8:05 a.m.-2:53 p.m.

1 stop5h 48m

C$ 358

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 10/10

12:45 p.m.-6:12 p.m.

1 stop6h 27m

Winnipeg

Sat 17/10

3:20 p.m.-10:40 p.m.

1 stop6h 20m

C$ 361

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 16/10

6:00 a.m.-11:12 a.m.

1 stop6h 12m

Winnipeg

Mon 19/10

3:20 p.m.-10:40 p.m.

1 stop6h 20m

C$ 361

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 22/9

4:30 p.m.-12:55 a.m.

3 stops33h 25m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 393

Flights are sorted by cheapest round-trip 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 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, August is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 602). Flying from Boston to Winnipeg in February is currently the most expensive (average of C$ 1,266). 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 7h 39m. Fly via Air Canada to get the fastest option. Boston and Winnipeg are separated by a distance of 2173 km.

  • 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, August is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 602). Flying from Boston to Winnipeg in February is currently the most expensive (average of C$ 1,266). 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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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.

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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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