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Winnipeg

$186+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
feb. 19 — feb. 261
jue. 2/19
jue. 2/26
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 enero 20, 2026.

This Trip.com deal was found by Cheapflights users on 1/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/76:25 pm
BOS
-
YWG
1 stop24h 15m
WestJet
dom. 5/106:30 am
YWG
-
BOS
1 stop10h 10m
WestJet
Deal found 1/19$377
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
dom. 5/316:25 pm
BOS
-
YWG
1 stop16h 35m
WestJet
vie. 6/56:30 am
YWG
-
BOS
1 stop10h 10m
WestJet
Deal found 1/19$390
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
sáb. 3/1412:36 pm
BOS
-
YWG
1 stop27h 33m
Multiple Airlines
lun. 3/238:00 am
YWG
-
BOS
1 stop30h 28m
Multiple Airlines
Deal found 1/19$393
This oojo deal was found by Cheapflights users on 1/19. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/176:25 pm
BOS
-
YWG
1 stop26h 50m
WestJet
sáb. 5/236:30 am
YWG
-
BOS
1 stop10h 10m
WestJet
Deal found 1/19$408
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
mar. 3/313:30 pm
BOS
-
YWG
2 stops9h 05m
Multiple Airlines
dom. 4/57:30 am
YWG
-
BOS
1 stop16h 56m
Multiple Airlines
Deal found 1/19$412
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
mié. 3/254:23 pm
BOS
-
YWG
2 stops20h 09m
Multiple Airlines
lun. 3/308:00 am
YWG
-
BOS
1 stop14h 59m
Multiple Airlines
Deal found 1/20$427
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
jue. 4/235:40 am
BOS
-
YWG
2 stops14h 29m
Multiple Airlines
lun. 4/276:30 am
YWG
-
BOS
1 stop10h 10m
Multiple Airlines
Deal found 1/19$436
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
lun. 3/166:24 pm
BOS
-
YWG
2 stops20h 28m
Multiple Airlines
lun. 3/238:00 am
YWG
-
BOS
1 stop14h 59m
Multiple Airlines
Deal found 1/19$447
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
vie. 5/293:30 pm
BOS
-
YWG
1 stop8h 16m
Multiple Airlines
mar. 6/26:30 am
YWG
-
BOS
1 stop10h 10m
Multiple Airlines
Deal found 1/19$461

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 enero 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$377
(Trip.com)

One-way from

$186
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$580
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
One-way flight 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 January 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 enero 20, 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

dom. 5/17

6:25 pm-8:15 pm

1 stop26h 50m

Winnipeg

sáb. 5/23

6:30 am-5:40 pm

1 stop10h 10m

$408

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mié. 3/25

4:23 pm-11:32 am

2 stops20h 09m

Winnipeg

lun. 3/30

8:00 am-11:59 pm

1 stop14h 59m

$427

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mié. 3/25

4:23 pm-3:30 pm

2 stops24h 07m

Winnipeg

mar. 3/31

8:00 am-9:33 pm

1 stop12h 33m

$504

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

jue. 4/23

5:35 am-7:09 pm

2 stops14h 34m

Winnipeg

lun. 4/27

10:45 am-11:53 pm

2 stops12h 08m

$556

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

jue. 4/23

3:30 pm-11:13 am

1 stop20h 43m

Winnipeg

lun. 4/27

9:05 pm-5:40 pm

1 stop19h 35m

$566

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mié. 3/25

9:05 am-7:09 pm

2 stops11h 04m

Winnipeg

mar. 3/31

5:00 am-2:11 pm

2 stops8h 11m

$579

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mié. 6/3

5:40 am-11:34 am

1 stop6h 54m

Winnipeg

vie. 6/5

6:40 am-5:19 pm

1 stop9h 39m

$592

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mié. 6/3

8:00 am-8:48 pm

2 stops13h 48m

Winnipeg

sáb. 6/6

7:00 am-6:44 pm

2 stops10h 44m

$592

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

mié. 6/3

5:40 am-11:34 am

1 stop6h 54m

Winnipeg

jue. 6/4

12:40 pm-11:52 pm

1 stop10h 12m

$592

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

sáb. 5/30

6:00 am-11:39 am

1 stop6h 39m

Winnipeg

sáb. 6/6

7:00 am-9:33 pm

1 stop13h 33m

$592

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 14 results
1
2

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 Expedia the most. Expedia 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 16, 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.

How much does it cost to fly round-trip from Boston to Winnipeg?

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 enero 20, 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
8,085 reviews

Boarding

8.1

Food

7.2

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

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
8,085 reviews
Delta
7.9
Good
8,085 reviews

Boarding

8.1

Food

7.2

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

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
9,189 reviews
Delta
7.9
Good
8,085 reviews

Boarding

8.1

Food

7.2

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

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
10,644 reviews
Delta
7.9
Good
8,085 reviews

Boarding

8.1

Food

7.2

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

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.

  • How long is the flight from Boston to Winnipeg?

    Departing from Boston to Winnipeg will take you 26h 50m. The distance between Boston and Winnipeg is about 1350 mi.

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

    Currently priced at $131, Delta will fly you from Boston to Winnipeg and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Air Canada and United Airlines - these airlines can fly you to your destination from $134 and $172, respectively. Delta 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, 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

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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.
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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 enero 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$131Average$420FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$134Average$429FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$172Average$586FlexibilityNo cancel feeOn-time69%

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