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$119+ Cheap flights from Boston (BOS) to Winnipeg (YWG)

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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Winnipeg are usually found in July or January, booked 67 days in advance, depart on a Sunday or Friday and return on a Saturday

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 September 16, 2025.

Round-trip from

$263
(Kiwi.com)

One-way from

$119
(Air Canada)

Popular in

February

Cheapest in

July

Average price

$526
From Boston Logan Intl to Winnipeg
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One-way flight from Boston Logan Intl to Winnipeg
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Highest demand for flights based on searches. 5% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Boston to Winnipeg

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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:30 pmBOS - YWG
1 stop18h 11mMultiple Airlines
Fri 10/317:30 amYWG - BOS
1 stop26h 18mMultiple Airlines
Deal found 9/13$263
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:24 pmBOS - YWG
2 stops20h 58mMultiple Airlines
Mon 10/206:30 amYWG - BOS
1 stop10h 10mMultiple Airlines
Deal found 9/15$280
This Air Canada deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/110:40 amBOS - YWG
1 stop8h 05mAir Canada
Wed 10/85:00 amYWG - BOS
1 stop5h 29mAir Canada
Deal found 9/16$286
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/185:45 amBOS - YWG
2 stops19h 57mMultiple Airlines
Wed 12/37:30 amYWG - BOS
1 stop15h 31mMultiple Airlines
Deal found 9/16$292
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:00 pmBOS - YWG
2 stops29h 40mMultiple Airlines
Thu 10/27:00 pmYWG - BOS
1 stop21h 40mMultiple Airlines
Deal found 9/15$331
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/213:00 pmBOS - YWG
2 stops34h 13mMultiple Airlines
Mon 10/277:40 amYWG - BOS
1 stop10h 36mMultiple Airlines
Deal found 9/16$340
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2312:49 pmBOS - YWG
2 stops12h 24mMultiple Airlines
Fri 10/314:00 pmYWG - BOS
1 stop15h 28mMultiple Airlines
Deal found 9/13$342
This Air Canada deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:45 pmBOS - YWG
1 stop7h 09mAir Canada
Sat 11/18:15 amYWG - BOS
1 stop5h 37mAir Canada
Deal found 9/13$344
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/243:30 pmBOS - YWG
2 stops10h 12mMultiple Airlines
Wed 12/37:30 amYWG - BOS
1 stop15h 31mMultiple Airlines
Deal found 9/16$348
This Air Canada deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:00 amBOS - YWG
2 stops11h 15mAir Canada
Fri 10/311:45 pmYWG - BOS
1 stop6h 42mAir Canada
Deal found 9/13$349

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 2,558,603 searches. Data last updated September 16, 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

Thu 10/16

8:24 pm-4:22 pm

2 stops20h 58m

Winnipeg

Mon 10/20

6:30 am-5:40 pm

1 stop10h 10m

$280

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 10/1

10:40 am-5:45 pm

1 stop8h 05m

Winnipeg

Wed 10/8

5:00 am-11:29 am

1 stop5h 29m

$286

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 10/25

6:00 am-3:31 pm

1 stop10h 31m

Winnipeg

Mon 11/3

8:40 am-11:39 pm

1 stop13h 59m

$352

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/23

8:00 am-10:33 pm

1 stop15h 33m

Winnipeg

Sat 11/1

2:20 pm-9:49 pm

1 stop6h 29m

$352

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 10/20

7:15 pm-9:41 am

1 stop15h 26m

Winnipeg

Tue 10/28

12:20 pm-10:05 pm

1 stop8h 45m

$352

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/23

11:02 am-10:33 pm

1 stop12h 31m

Winnipeg

Wed 10/29

2:20 pm-9:49 pm

1 stop6h 29m

$352

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 10/24

6:00 am-5:45 pm

2 stops12h 45m

Winnipeg

Sat 11/1

6:00 am-2:52 pm

2 stops7h 52m

$354

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 10/24

6:00 am-5:45 pm

2 stops12h 45m

Winnipeg

Tue 10/28

6:00 am-2:52 pm

2 stops7h 52m

$354

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 10/24

6:00 am-5:45 pm

2 stops12h 45m

Winnipeg

Mon 11/3

5:30 am-7:12 pm

2 stops12h 42m

$361

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 10/23

6:00 am-10:33 pm

1 stop17h 33m

Winnipeg

Tue 10/28

8:40 am-10:47 pm

2 stops13h 07m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 16 results
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

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 September 12, 2025.

Booking 67 days in advance of your planned departure date is, on average, the best time to get cheap flights from Boston to Winnipeg. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 $358). Flying from Boston to Winnipeg in December is currently the most expensive (average of $501). 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.

What is the cheapest time of day to fly from BOS to YWG?

Find hourly flight availability from Boston to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

It’s typically best to fly out from Boston to Winnipeg at noon. Doing so could potentially save you 27% on the flight price compared to flying in the afternoon, which is usually more expensive.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated September 16, 2025.
Peruse reviews from past customers who have flown with Delta, Porter Airlines, and United Airlines from Boston to Winnipeg to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Porter Airlines
7.9
Good
363 reviews
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,924 reviews
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
10,000 reviews
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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?

    Departing from Boston to Winnipeg will take you 8h 05m. The distance between Boston and Winnipeg is about 1350 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Boston to Winnipeg round-trip?

    Currently priced at $134, Air Canada will fly you from Boston to Winnipeg and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Delta - these airlines can fly you to your destination from $172 and $274, respectively. Air Canada is currently priced 69% below the average price you’ll pay for this route.

  • 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 $358). Flying from Boston to Winnipeg in December is currently the most expensive (average of $501). 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

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Complete your trip

Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
Winnipeg car rentals
Winnipeg Airport car rentals

Top 4 airlines flying from Boston to Winnipeg

Discover the top 4 airlines that operate flights from Boston to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$134Average$425FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$172Average$559FlexibilityNo cancel feeOn-time69%
DeltaCheapest$274Average$424FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$283Average$438FlexibilityNo cancel feeOn-time52%

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