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Cheap flights from Boston to Winnipeg from C$ 168

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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Boston Logan Intl to Winnipeg are usually found in July or January, booked 63 days in advance, depart on a Tuesday or Monday and return on a Tuesday

Cheap 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 28 October 2025.

Round-trip from

C$ 438

One-way from

C$ 168

Popular in

February

Cheapest in

July

Average price

C$ 583
11/11-13/11
  • 11/11-13/11
  • 6 total stops
  • 57h 05m total
  • Boston to Winnipeg
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12/12
  • 12/12
  • 3 total stops
  • 33h 47m total
  • Boston to Winnipeg
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Highest demand for flights based on searches. 5% potential increase in price (C$ 45 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 24 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 28 October 2025.

Tue 11/1112:00 p.m.BOS - YWG
3 stops31h 06mMultiple Airlines
Thu 13/119:00 p.m.YWG - BOS
3 stops25h 59mMultiple Airlines
Deal found 27/10C$ 438
Thu 11/1211:28 a.m.BOS - YWG
1 stop28h 39mMultiple Airlines
Thu 18/129:05 a.m.YWG - BOS
2 stops13h 01mMultiple Airlines
Deal found 26/10C$ 460
Sun 9/117:00 a.m.BOS - YWG
2 stops18h 43mMultiple Airlines
Wed 12/117:30 a.m.YWG - BOS
1 stop24h 30mMultiple Airlines
Deal found 26/10C$ 530
Tue 11/111:25 p.m.BOS - YWG
1 stop12h 17mMultiple Airlines
Wed 12/117:30 a.m.YWG - BOS
1 stop24h 30mMultiple Airlines
Deal found 27/10C$ 583
Thu 6/1112:20 p.m.BOS - YWG
2 stops27h 47mMultiple Airlines
Mon 10/115:00 a.m.YWG - BOS
1 stop8h 55mMultiple Airlines
Deal found 26/10C$ 603
Thu 11/1211:28 a.m.BOS - YWG
1 stop28h 39mMultiple Airlines
Fri 19/124:25 p.m.YWG - BOS
2 stops16h 10mMultiple Airlines
Deal found 27/10C$ 607

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 28 October 2025.
Use the filters below to find and compare flights from Boston to Winnipeg that are best for you.

Fly from

Boston

Fly to

Winnipeg

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 11/11

12:00 p.m.-6:06 p.m.

3 stops31h 06m

Winnipeg

Thu 13/11

9:00 p.m.-11:59 p.m.

3 stops25h 59m

C$ 438

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 11/12

11:28 a.m.-3:07 p.m.

1 stop28h 39m

Winnipeg

Thu 18/12

9:05 a.m.-11:06 p.m.

2 stops13h 01m

C$ 460

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 9/11

7:00 a.m.-12:43 a.m.

2 stops18h 43m

Winnipeg

Wed 12/11

7:30 a.m.-9:00 a.m.

1 stop24h 30m

C$ 530

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 11/11

1:25 p.m.-12:42 a.m.

1 stop12h 17m

Winnipeg

Wed 12/11

7:30 a.m.-9:00 a.m.

1 stop24h 30m

C$ 583

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 11/12

11:28 a.m.-3:07 p.m.

1 stop28h 39m

Winnipeg

Fri 19/12

5:45 p.m.-11:06 p.m.

1 stop28h 21m

C$ 585

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 16/1

6:00 a.m.-3:07 p.m.

1 stop10h 07m

Winnipeg

Tue 20/1

5:00 a.m.-12:40 a.m.

2 stops18h 40m

C$ 597

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 24/12

7:15 p.m.-11:45 a.m.

2 stops17h 30m

Winnipeg

Fri 26/12

5:45 p.m.-11:54 p.m.

1 stop5h 09m

C$ 718

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 12/12

11:19 a.m.-8:06 p.m.

3 stops33h 47m

C$ 168

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 11/11

6:16 a.m.-8:06 p.m.

3 stops38h 50m

C$ 180

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 27/12

5:30 a.m.-10:16 a.m.

1 stop5h 46m

C$ 324

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/10

Showing 1-10 of 15 results
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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

How far ahead should I book a flight from Boston to Winnipeg?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Winnipeg. Price data was last updated on 24 October 2025.

The price you pay for your flight from Boston to Winnipeg may vary depending on when you book. For the best chance of a lower fare, look to book 63 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, July is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 179). Flying from Boston to Winnipeg in April is currently the most expensive (average of C$ 604). 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?

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.

  • 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, July is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 179). Flying from Boston to Winnipeg in April is currently the most expensive (average of C$ 604). 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
Portage la Prairie

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Alternative routes for Boston to Winnipeg

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Hartford to Winnipeg flights

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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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