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Winnipeg

$136+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Winnipeg are usually found in January or October, booked 22 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 July 1, 2025.

Round-trip from

$301
(Flightnetwork)

One-way from

$136
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$388
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. 18% potential increase in price ($104 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 1, 2025.

This Flightnetwork deal was found by Cheapflights users on 6/30. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1810:20 amBOS - YWG
1 stop5h 40mAir Canada
Sat 10/257:55 amYWG - BOS
1 stop5h 35mAir Canada
Deal found 6/30$294
This oojo deal was found by Cheapflights users on 6/29. 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.
Mon 9/156:30 pmBOS - YWG
1 stop18h 11mWestJet
Sun 9/215:30 pmYWG - BOS
1 stop23h 10mWestJet
Deal found 6/29$319
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Fri 9/56:00 amBOS - YWG
1 stop5h 40mMultiple Airlines
Mon 9/87:00 pmYWG - BOS
3 stops21h 38mMultiple Airlines
Deal found 6/30$339
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/216:09 amBOS - YWG
1 stop17h 24mUnited Airlines
Mon 8/255:00 amYWG - BOS
1 stop5h 28mUnited Airlines
Deal found 6/30$353
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/77:40 amBOS - YWG
2 stops13h 30mDelta
Fri 8/225:41 pmYWG - BOS
1 stop5h 37mDelta
Deal found 6/29$404

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 July 1, 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

Sat 10/18

10:20 am-3:00 pm

1 stop5h 40m

Winnipeg

Sat 10/25

7:55 am-2:30 pm

1 stop5h 35m

$294

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 9/15

6:30 pm-11:41 am

1 stop18h 11m

Winnipeg

Sun 9/21

5:30 pm-5:40 pm

1 stop23h 10m

$319

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 9/5

6:00 am-10:40 am

1 stop5h 40m

Winnipeg

Mon 9/8

7:00 pm-5:38 pm

3 stops21h 38m

$339

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 8/21

6:09 am-10:33 pm

1 stop17h 24m

Winnipeg

Mon 8/25

5:00 am-11:28 am

1 stop5h 28m

$353

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 8/7

7:40 am-8:10 pm

2 stops13h 30m

Winnipeg

Fri 8/22

5:41 pm-12:18 am

1 stop5h 37m

$404

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 8/11

6:30 pm-8:10 pm

1 stop26h 40m

$136

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/25

6:30 pm-9:01 am

1 stop15h 31m

$137

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 7/28

8:48 pm-1:09 pm

1 stop17h 21m

$151

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 11/27

10:35 am-4:35 pm

1 stop7h 00m

$154

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 8/1

12:15 pm-10:46 pm

2 stops11h 31m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 11 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 June 27, 2025.

Booking 20 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 $497). 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 July 1, 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 July 1, 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
298 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
298 reviews
Porter Airlines
8.0
Very good
298 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,973 reviews
Porter Airlines
8.0
Very good
298 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,858 reviews
Porter Airlines
8.0
Very good
298 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,909 reviews
Porter Airlines
8.0
Very good
298 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Canada
7.1
Good
9,665 reviews
Porter Airlines
8.0
Very good
298 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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 $301, 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 WestJet and United Airlines - these airlines can fly you to your destination from $319 and $353, respectively. Air Canada is currently priced 35% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Boston to Winnipeg one-way?

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as $137. However, be on the lookout for offers from United Airlines and Air Canada, as they are both options that can get you from Boston to Winnipeg for a low price.

  • 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 $497). 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

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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$134Average$447FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$172Average$569FlexibilityNo cancel feeOn-time69%
DeltaCheapest$274Average$458FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$283Average$438FlexibilityNo cancel feeOn-time52%

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