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$145+ Cheap flights from Winnipeg (YWG) to Boston (BOS)

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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Boston Logan Intl are usually found in October or August, booked 87 days in advance, depart on a Saturday or Wednesday and return on a Sunday

Cheap flight deals from Winnipeg to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Boston (BOS). 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 17, 2025.

Round-trip from

$217
(Trip.com)

One-way from

$145
(Air Canada)

Popular in

December

Cheapest in

October

Average price

$357
From Winnipeg to Boston Logan Intl
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One-way flight from Winnipeg to Boston Logan Intl
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Highest demand for flights based on searches. 23% potential increase in price ($122 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 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 Winnipeg to Boston

Cheapest flights from Winnipeg to Boston
Explore the most affordable flight options available from Winnipeg to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:00 amYWG - BOS
1 stop5h 29mAir Canada
Wed 10/2210:20 amBOS - YWG
1 stop5h 40mAir Canada
Deal found 9/16$217
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/712:20 pmYWG - BOS
1 stop8h 44mDelta
Wed 10/155:45 amBOS - YWG
1 stop6h 45mDelta
Deal found 9/15$250
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.
Wed 11/197:30 amYWG - BOS
2 stops25h 54mMultiple Airlines
Wed 12/36:00 amBOS - YWG
1 stop10h 07mMultiple Airlines
Deal found 9/16$274
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/712:20 pmYWG - BOS
1 stop8h 44mDelta
Sun 10/128:10 amBOS - YWG
1 stop9h 40mDelta
Deal found 9/16$288
This United 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/242:20 pmYWG - BOS
1 stop9h 30mMultiple Airlines
Sun 11/25:30 amBOS - YWG
1 stop5h 46mMultiple Airlines
Deal found 9/15$296
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 12/57:30 amYWG - BOS
1 stop16h 14mMultiple Airlines
Mon 12/86:55 pmBOS - YWG
1 stop17h 40mMultiple Airlines
Deal found 9/15$315
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.
Tue 11/188:15 amYWG - BOS
1 stop5h 37mAir Canada
Thu 12/45:30 amBOS - YWG
1 stop5h 46mAir Canada
Deal found 9/16$327
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.
Tue 11/186:00 amYWG - BOS
2 stops7h 52mAir Canada
Fri 11/2810:15 amBOS - YWG
1 stop7h 20mAir Canada
Deal found 9/16$332

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Boston 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 17, 2025.
Use the filters below to find and compare flights from Winnipeg to Boston that are best for you.

Fly from

Winnipeg

Fly to

Boston

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 10/16

5:00 am-11:29 am

1 stop5h 29m

Boston Logan Intl

Wed 10/22

10:20 am-3:00 pm

1 stop5h 40m

$217

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 10/7

12:20 pm-10:04 pm

1 stop8h 44m

Boston Logan Intl

Wed 10/15

5:45 am-11:30 am

1 stop6h 45m

$250

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 10/7

12:20 pm-10:04 pm

1 stop8h 44m

Boston Logan Intl

Sun 10/12

8:10 am-4:50 pm

1 stop9h 40m

$288

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 10/24

2:20 pm-12:50 am

1 stop9h 30m

Boston Logan Intl

Sun 11/2

5:30 am-10:16 am

1 stop5h 46m

$296

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 12/5

7:30 am-12:44 am

1 stop16h 14m

Boston Logan Intl

Mon 12/8

6:55 pm-11:35 am

1 stop17h 40m

$315

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 11/24

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Wed 12/3

5:30 am-10:16 am

1 stop5h 46m

$327

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 11/22

1:45 pm-9:27 pm

1 stop6h 42m

Boston Logan Intl

Tue 12/2

5:30 am-10:16 am

1 stop5h 46m

$327

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 11/20

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Tue 12/2

5:30 am-10:16 am

1 stop5h 46m

$327

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 10/25

5:00 am-11:29 am

1 stop5h 29m

$145

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 10/24

2:20 pm-12:50 am

1 stop9h 30m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 17 results
1
2

Best time to book a flight from Winnipeg to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Winnipeg 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 Winnipeg to Boston

How far ahead should I book a flight from Winnipeg to Boston?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Boston. Price data was last updated on September 12, 2025.

The best time to book flights from Winnipeg to Boston is 87 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Winnipeg to Boston?

Currently, January is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $218). Flying from Winnipeg to Boston in July is currently the most expensive (average of $311). 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 Winnipeg to Boston?

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated September 17, 2025.
Read reviews from past customers who have flown Delta, Porter Airlines, and United Airlines from Winnipeg to Boston. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Porter Airlines
7.9
Good
365 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,926 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Air Canada
7.1
Good
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Boston. 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 Winnipeg to Boston?

    For as low as $217, Air Canada can have you in Boston from Winnipeg in 5h 29m. Airlines will cover a distance of 1350 mi. This flight may include one or multiple stops.

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

    According to our current data, United Airlines ($100), Delta ($241), and Air Canada ($254) offers the cheapest pricing from Winnipeg to Boston. United Airlines is 75% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest airlines for a one-way flight from Winnipeg to Boston are Air Canada ($145), United Airlines ($149), and Delta ($152).

  • Can I find deals for flights from Winnipeg to Boston that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Boston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Boston.

  • Can I find deals for business class flights from Winnipeg to Boston?

    Yes. Cheapflights offers flight deals from Winnipeg to Boston 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 Winnipeg to Boston?

    Currently, January is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $218). Flying from Winnipeg to Boston in July is currently the most expensive (average of $311). 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 Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Chelsea
Warwick
Peabody
Quincy
York Beach
Swansea
Old Orchard Beach
Brockton
Waltham

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Winnipeg to Boston

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Albany flights

Top 4 airlines flying from Winnipeg to Boston

Discover the top 4 airlines that operate flights from Winnipeg to Boston. 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$369FlexibilityNo cancel feeOn-time69%
DeltaCheapest$241Average$464FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$254Average$419FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$267Average$355FlexibilityNo cancel feeOn-time52%

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