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Winnipeg

$307+ Cheap flights from Boston (BOS) to Winnipeg (YWG)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap 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 February 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Sun 5/34:45 pm
BOS
-
YWG
1 stop9h 10m
Multiple Airlines
Thu 5/79:05 pm
YWG
-
BOS
2 stops13h 40m
Multiple Airlines
Deal found 2/4$307
This Mytrip deal was found by Cheapflights users on 2/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:40 am
BOS
-
YWG
3 stops36h 45m
Multiple Airlines
Mon 5/189:05 pm
YWG
-
BOS
3 stops18h 53m
Multiple Airlines
Deal found 2/4$371
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/66:00 am
BOS
-
YWG
1 stop10h 09m
Multiple Airlines
Mon 3/98:00 am
YWG
-
BOS
1 stop32h 15m
Multiple Airlines
Deal found 2/3$375
This Air Canada deal was found by Cheapflights users on 2/2. 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.
Thu 2/265:30 am
BOS
-
YWG
1 stop5h 45m
Air Canada
Thu 2/261:30 pm
YWG
-
BOS
1 stop8h 07m
Air Canada
Deal found 2/2$405
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 5/2210:05 am
BOS
-
YWG
1 stop7h 20m
Multiple Airlines
Sat 5/306:00 am
YWG
-
BOS
1 stop8h 50m
Multiple Airlines
Deal found 2/2$421

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$375
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$470
Provider with most accurate pricing for Boston Logan Intl-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Winnipeg flights.
Search Deals
From Boston Logan Intl to Winnipeg
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($113 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 2,558,603 searches. Data last updated February 4, 2026.
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 5/14

5:40 am-5:25 pm

3 stops36h 45m

Winnipeg

Mon 5/18

9:05 pm-4:58 pm

3 stops18h 53m

$371

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 3/6

6:00 am-3:09 pm

1 stop10h 09m

Winnipeg

Mon 3/9

8:00 am-5:15 pm

1 stop32h 15m

$375

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 5/3

4:45 pm-12:55 am

1 stop9h 10m

Winnipeg

Thu 5/7

5:10 pm-10:31 am

1 stop16h 21m

$402

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 2/26

5:30 am-10:15 am

1 stop5h 45m

Winnipeg

Thu 2/26

1:30 pm-10:37 pm

1 stop8h 07m

$405

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 5/22

10:05 am-4:25 pm

1 stop7h 20m

Winnipeg

Sat 5/30

6:15 am-11:59 pm

2 stops16h 44m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Compare providers for flights from Boston to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Winnipeg in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Boston-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 January 30, 2026.

Booking 50 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, May is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $118). Flying from Boston to Winnipeg in April is currently the most expensive (average of $449). 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.

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 February 4, 2026.
Peruse reviews from past customers who have flown with Delta, United Airlines, and Air Canada 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
7.9
Good
8,146 reviews

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,146 reviews
Delta
7.9
Good
8,146 reviews

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,236 reviews
Delta
7.9
Good
8,146 reviews

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Air Canada
7.1
Good
10,688 reviews
Delta
7.9
Good
8,146 reviews

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

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

    Currently priced at $128, 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 Delta and United Airlines - these airlines can fly you to your destination from $131 and $172, respectively. Air Canada is currently priced 70% 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, May is the cheapest month in which you can book a flight from Boston to Winnipeg (average of $118). Flying from Boston to Winnipeg in April is currently the most expensive (average of $449). 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 3 airlines flying from Boston to Winnipeg

Discover the top 3 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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$128Average$426FlexibilityNo cancel feeOn-time67%
DeltaCheapest$131Average$420FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$172Average$586FlexibilityNo cancel feeOn-time69%

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