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Cheap flights from Boston to Winnipeg from C$ 310

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 17/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Boston Logan Intl to Winnipeg are usually found in July or August, booked 22 days in advance, depart on a Tuesday or Monday and return on a Tuesday

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 12 December 2025.

Fri 12/1212:17 p.m.BOS - YWG
2 stops32h 18mMultiple Airlines
Mon 15/128:00 a.m.YWG - BOS
1 stop14h 56mMultiple Airlines
Deal found 11/12C$ 1,000
Tue 16/1210:20 a.m.BOS - YWG
1 stop10h 15mMultiple Airlines
Wed 17/127:30 a.m.YWG - BOS
2 stops26h 57mMultiple Airlines
Deal found 9/12C$ 1,078
Sun 28/127:00 a.m.BOS - YWG
1 stop17h 35mMultiple Airlines
Fri 2/18:20 p.m.YWG - BOS
1 stop12h 15mMultiple Airlines
Deal found 10/12C$ 1,110
Tue 16/128:11 p.m.BOS - YWG
2 stops24h 24mMultiple Airlines
Wed 24/127:30 a.m.YWG - BOS
1 stop25h 38mMultiple Airlines
Deal found 11/12C$ 1,194
Tue 23/122:15 p.m.BOS - YWG
2 stops22h 42mUnited Airlines
Sat 27/122:20 p.m.YWG - BOS
1 stop9h 25mUnited Airlines
Deal found 11/12C$ 1,209
Tue 16/1210:56 a.m.BOS - YWG
2 stops33h 39mMultiple Airlines
Mon 22/128:00 a.m.YWG - BOS
1 stop14h 57mMultiple Airlines
Deal found 11/12C$ 1,245
Fri 12/125:45 a.m.BOS - YWG
2 stops14h 50mMultiple Airlines
Sun 14/127:30 a.m.YWG - BOS
1 stop25h 52mMultiple Airlines
Deal found 11/12C$ 1,248

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 12 December 2025.

Round-trip from

C$ 367

One-way from

C$ 310

Popular in

December

Cheapest in

July

Average price

C$ 858
6/2-8/2
  • 6/2-8/2
  • 2 total stops
  • 26h 53m total
  • Boston to Winnipeg
Search Deals
Porter Airlines
  • Porter Airlines
  • 17/5
  • 1 total stop
  • 7h 56m total
  • Boston to Winnipeg
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 159 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 12 December 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

Sun 25/1

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

1 stop10h 07m

Winnipeg

Sun 1/2

7:30 a.m.-1:13 a.m.

1 stop16h 43m

C$ 400

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/1

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

1 stop5h 46m

Winnipeg

Wed 7/1

8:15 a.m.-2:52 p.m.

1 stop5h 37m

C$ 465

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 3/2

5:30 a.m.-10:15 a.m.

1 stop5h 45m

Winnipeg

Sat 7/2

8:15 a.m.-2:52 p.m.

1 stop5h 37m

C$ 535

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 25/1

3:30 p.m.-11:35 p.m.

2 stops9h 05m

Winnipeg

Sun 1/2

4:25 p.m.-11:05 a.m.

2 stops17h 40m

C$ 610

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 6/1

2:30 p.m.-12:42 a.m.

2 stops11h 12m

Winnipeg

Fri 9/1

4:25 p.m.-6:10 p.m.

1 stop24h 45m

C$ 626

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 1/1

3:40 p.m.-11:13 a.m.

3 stops20h 33m

Winnipeg

Wed 7/1

7:50 a.m.-2:52 p.m.

3 stops30h 02m

C$ 728

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 6/2

3:30 p.m.-11:35 p.m.

2 stops9h 05m

Winnipeg

Sun 8/2

5:00 a.m.-11:51 p.m.

2 stops17h 51m

C$ 765

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 12/1

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

1 stop5h 46m

Winnipeg

Tue 13/1

8:15 a.m.-2:52 p.m.

1 stop5h 37m

C$ 772

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 17/5

3:50 p.m.-10:46 p.m.

1 stop7h 56m

C$ 310

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 18/5

3:30 p.m.-10:46 p.m.

1 stop8h 16m

C$ 324

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 13 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 5 December 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 20 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$ 177). Flying from Boston to Winnipeg in April is currently the most expensive (average of C$ 619). 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.

  • How long is the flight from Boston to Winnipeg?

    There are many flights that can get you from Boston to Winnipeg in 5h 46m. 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, July is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 177). Flying from Boston to Winnipeg in April is currently the most expensive (average of C$ 619). 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

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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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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