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Cheap flights from Boston to Winnipeg from C$ 229

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 14/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
23 Aug — 30 Aug1
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
Explore the most affordable flight options available from Boston to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 July 2026.

Mon 21/97:30 p.m.
BOS
-
YWG
1 stop6h 25m
Multiple Airlines
Wed 23/96:15 a.m.
YWG
-
BOS
1 stop9h 31m
Multiple Airlines
Deal found 20/7C$ 472
Fri 11/910:40 a.m.
BOS
-
YWG
1 stop5h 29m
Air Canada
Sat 19/93:20 p.m.
YWG
-
BOS
1 stop6h 20m
Air Canada
Deal found 23/7C$ 484
Fri 11/98:25 p.m.
BOS
-
YWG
2 stops22h 33m
Multiple Airlines
Sat 19/96:15 a.m.
YWG
-
BOS
1 stop9h 31m
Multiple Airlines
Deal found 23/7C$ 486
Mon 14/97:30 p.m.
BOS
-
YWG
1 stop15h 15m
Multiple Airlines
Tue 22/911:15 a.m.
YWG
-
BOS
2 stops22h 15m
Multiple Airlines
Deal found 21/7C$ 491
Fri 11/98:25 p.m.
BOS
-
YWG
2 stops22h 33m
Multiple Airlines
Wed 16/97:45 a.m.
YWG
-
BOS
1 stop9h 50m
Multiple Airlines
Deal found 24/7C$ 498
Sat 29/87:10 a.m.
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Sat 5/912:15 p.m.
YWG
-
BOS
1 stop6h 00m
Porter Airlines
Deal found 19/7C$ 508
Mon 21/97:30 p.m.
BOS
-
YWG
1 stop15h 15m
Multiple Airlines
Wed 30/96:15 a.m.
YWG
-
BOS
1 stop11h 20m
Multiple Airlines
Deal found 21/7C$ 511

Find flight deals from Boston to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 24 July 2026.

Round-trip from

C$ 472

One-way from

C$ 229

Popular in

February

Cheapest in

May

Average price

C$ 748
21/9-23/9
  • 21/9-23/9
  • 2 total stops
  • 15h 56m total
  • Boston to Winnipeg
Search Deals
14/9
  • 14/9
  • 1 total stop
  • 15h 15m total
  • Boston to Winnipeg
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 289 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 54 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights 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, Cheapflights users made 629,999 searches. Data last updated 24 July 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

Mon 14/9

7:30 p.m.-9:45 a.m.

1 stop15h 15m

Winnipeg

Tue 22/9

11:15 a.m.-10:30 a.m.

2 stops22h 15m

C$ 491

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 29/8

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

2 stops11h 48m

Winnipeg

Sat 5/9

12:15 p.m.-7:15 p.m.

1 stop6h 00m

C$ 508

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 11/9

3:55 p.m.-9:45 a.m.

2 stops18h 50m

Winnipeg

Wed 16/9

9:05 p.m.-7:41 p.m.

3 stops21h 36m

C$ 553

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 17/8

8:31 p.m.-11:52 a.m.

1 stop16h 21m

Winnipeg

Wed 19/8

7:00 a.m.-4:27 p.m.

1 stop8h 27m

C$ 574

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 11/8

5:51 a.m.-3:08 p.m.

1 stop10h 17m

Winnipeg

Thu 13/8

12:46 p.m.-11:58 p.m.

1 stop10h 12m

C$ 574
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 19/9

10:40 a.m.-6:12 p.m.

2 stops8h 32m

Winnipeg

Tue 22/9

8:10 a.m.-2:41 p.m.

1 stop5h 31m

C$ 579

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 18/8

5:45 a.m.-10:33 p.m.

2 stops17h 48m

Winnipeg

Fri 21/8

2:00 p.m.-11:34 p.m.

1 stop8h 34m

C$ 588

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 11/8

5:45 a.m.-6:15 p.m.

2 stops13h 30m

Winnipeg

Thu 13/8

5:00 a.m.-11:52 a.m.

1 stop5h 52m

C$ 588

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 12/8

5:51 a.m.-11:54 a.m.

1 stop7h 03m

Winnipeg

Thu 13/8

12:46 p.m.-11:58 p.m.

1 stop10h 12m

C$ 590

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 12/8

7:10 a.m.-11:54 a.m.

1 stop5h 44m

Winnipeg

Fri 14/8

12:46 p.m.-11:58 p.m.

1 stop10h 12m

C$ 590

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/7

Showing 1-10 of 18 resultsSorted by cheapest first
1
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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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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, May is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 728). Flying from Boston to Winnipeg in February is currently the most expensive (average of C$ 1,292). 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$ 553 and C$ 982 in September.
The cheapest round-trip price found within the last 5 days was C$ 472 on Multiple Airlines (21 Sep-23 Sep).

Related info for your journey

Find useful and relevant information for your journey from Boston to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Boston to Winnipeg?

    There are many flights that can get you from Boston to Winnipeg in 11h 48m. Fly via Porter Airlines or United Airlines 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, May is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 728). Flying from Boston to Winnipeg in February is currently the most expensive (average of C$ 1,292). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Boston to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
Hartford to Winnipeg flights

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

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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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