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Winnipeg

$132+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
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 63 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 agosto 14, 2025.

Round-trip from

$287
(Kiwi.com)

One-way from

$132
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$382
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. 22% potential increase in price ($128 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/14. 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. 10/169:50 amBOS - YWG
2 stops15h 40mMultiple Airlines
lun. 10/206:30 amYWG - BOS
1 stop10h 10mMultiple Airlines
Deal found 8/14$287
This Kiwi.com deal was found by Cheapflights users on 8/12. 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. 10/169:50 amBOS - YWG
2 stops15h 40mMultiple Airlines
vie. 10/246:30 amYWG - BOS
1 stop10h 10mMultiple Airlines
Deal found 8/12$289
This oojo deal was found by Cheapflights users on 8/13. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/277:00 pmBOS - YWG
1 stop20h 13mWestJet
sáb. 10/46:30 amYWG - BOS
1 stop10h 10mWestJet
Deal found 8/13$295
This Kiwi.com deal was found by Cheapflights users on 8/14. 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. 10/26:30 pmBOS - YWG
1 stop15h 31mMultiple Airlines
lun. 10/69:00 amYWG - BOS
1 stop9h 16mMultiple Airlines
Deal found 8/14$296
This Trip.com deal was found by Cheapflights users on 8/14. 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. 9/186:30 pmBOS - YWG
1 stop26h 45mWestJet
vie. 9/266:30 amYWG - BOS
1 stop10h 10mWestJet
Deal found 8/14$305
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
vie. 12/56:00 amBOS - YWG
1 stop10h 07mMultiple Airlines
dom. 12/77:30 amYWG - BOS
1 stop16h 14mMultiple Airlines
Deal found 8/13$311
This Trip.com deal was found by Cheapflights users on 8/14. 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.
dom. 9/287:00 pmBOS - YWG
1 stop20h 13mWestJet
dom. 10/58:15 pmYWG - BOS
1 stop20h 55mWestJet
Deal found 8/14$312
This Air Canada deal was found by Cheapflights users on 8/13. 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.
vie. 11/145:30 amBOS - YWG
1 stop5h 46mAir Canada
mar. 11/188:15 amYWG - BOS
1 stop5h 37mAir Canada
Deal found 8/13$316
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
sáb. 9/278:38 amBOS - YWG
2 stops16h 52mMultiple Airlines
sáb. 10/46:30 amYWG - BOS
1 stop10h 10mMultiple Airlines
Deal found 8/13$317
This oojo deal was found by Cheapflights users on 8/13. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/127:00 pmBOS - YWG
1 stop20h 13mWestJet
vie. 9/198:15 pmYWG - BOS
1 stop20h 55mWestJet
Deal found 8/13$318
This Air Canada deal was found by Cheapflights users on 8/14. 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.
jue. 10/1610:20 amBOS - YWG
1 stop5h 40mAir Canada
lun. 10/205:00 amYWG - BOS
1 stop5h 29mAir Canada
Deal found 8/14$323

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 agosto 14, 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

jue. 10/16

9:50 am-12:30 am

2 stops15h 40m

Winnipeg

lun. 10/20

6:30 am-5:40 pm

1 stop10h 10m

$287

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

jue. 10/16

9:50 am-12:30 am

2 stops15h 40m

Winnipeg

vie. 10/24

6:30 am-5:40 pm

1 stop10h 10m

$289

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

sáb. 9/27

7:00 pm-2:13 pm

1 stop20h 13m

Winnipeg

sáb. 10/4

6:30 am-5:40 pm

1 stop10h 10m

$295

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

jue. 10/2

6:30 pm-9:01 am

1 stop15h 31m

Winnipeg

lun. 10/6

9:00 am-7:16 pm

1 stop9h 16m

$296

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

jue. 9/18

6:30 pm-8:15 pm

1 stop26h 45m

Winnipeg

vie. 9/26

6:30 am-5:40 pm

1 stop10h 10m

$305

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

vie. 12/5

6:00 am-3:07 pm

1 stop10h 07m

Winnipeg

dom. 12/7

7:30 am-12:44 am

1 stop16h 14m

$311

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

jue. 11/27

10:15 am-4:35 pm

1 stop7h 20m

Winnipeg

lun. 12/1

7:05 pm-2:52 pm

2 stops18h 47m

$312

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

dom. 9/28

7:00 pm-2:13 pm

1 stop20h 13m

Winnipeg

dom. 10/5

8:15 pm-6:10 pm

1 stop20h 55m

$312

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

vie. 11/14

5:30 am-10:16 am

1 stop5h 46m

Winnipeg

mar. 11/18

8:15 am-2:52 pm

1 stop5h 37m

$316

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

sáb. 9/27

8:38 am-12:30 am

2 stops16h 52m

Winnipeg

sáb. 10/4

6:30 am-5:40 pm

1 stop10h 10m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 19 results
1
2

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 August 8, 2025.

Booking 63 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 $495). 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 agosto 14, 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 agosto 14, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta, 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.
Porter Airlines
8.0
Very good
332 reviews

Comfort

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
332 reviews
Porter Airlines
8.0
Very good
332 reviews

Comfort

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,980 reviews
Porter Airlines
8.0
Very good
332 reviews

Comfort

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,916 reviews
Porter Airlines
8.0
Very good
332 reviews

Comfort

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,949 reviews
Porter Airlines
8.0
Very good
332 reviews

Comfort

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 $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 $495). 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 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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$134Average$427FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$172Average$559FlexibilityNo cancel feeOn-time69%
DeltaCheapest$274Average$442FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$283Average$438FlexibilityNo cancel feeOn-time52%

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