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$146+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Boston Logan Intl are usually found in October or September, booked 55 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 August 14, 2025.

Round-trip from

$274
(Trip.com)

One-way from

$146
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$332
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. 24% potential increase in price ($128 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($23 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 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 August 14, 2025.

This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/155:00 amYWG - BOS
1 stop5h 29mAir Canada
Tue 9/236:00 amBOS - YWG
1 stop5h 40mAir Canada
Deal found 8/13$274
This Delta 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 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 10/1511:37 amBOS - YWG
1 stop9h 33mDelta
Deal found 8/14$281
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.
Tue 9/95:00 amYWG - BOS
1 stop5h 29mAir Canada
Tue 9/166:00 amBOS - YWG
1 stop5h 40mAir Canada
Deal found 8/13$282
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.
Tue 10/75:00 amYWG - BOS
2 stops11h 55mAir Canada
Wed 10/154:45 pmBOS - YWG
1 stop7h 40mAir Canada
Deal found 8/14$289
This United 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:00 amYWG - BOS
1 stop16h 50mMultiple Airlines
Tue 9/306:00 amBOS - YWG
1 stop5h 40mMultiple Airlines
Deal found 8/13$290
This United 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/97:00 amYWG - BOS
1 stop11h 19mMultiple Airlines
Tue 9/166:00 amBOS - YWG
2 stops11h 15mMultiple Airlines
Deal found 8/13$296
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.
Thu 9/259:00 amYWG - BOS
1 stop23h 58mMultiple Airlines
Thu 10/210:53 amBOS - YWG
2 stops14h 37mMultiple Airlines
Deal found 8/14$297
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/204:25 pmYWG - BOS
2 stops15h 59mUnited Airlines
Mon 9/225:30 amBOS - YWG
2 stops18h 03mUnited Airlines
Deal found 8/14$298
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/258:15 pmYWG - BOS
1 stop20h 55mWestJet
Thu 10/26:30 pmBOS - YWG
1 stop18h 11mWestJet
Deal found 8/14$312
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/265:40 pmYWG - BOS
1 stop5h 19mDelta
Tue 9/302:39 pmBOS - YWG
2 stops9h 48mDelta
Deal found 8/13$327

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 August 14, 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

Mon 9/15

5:00 am-11:29 am

1 stop5h 29m

Boston Logan Intl

Tue 9/23

6:00 am-10:40 am

1 stop5h 40m

$274

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 9/15

5:40 pm-11:59 pm

1 stop5h 19m

Boston Logan Intl

Tue 9/23

1:00 pm-11:27 pm

2 stops11h 27m

$281

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 10/7

5:40 pm-11:59 pm

1 stop5h 19m

Boston Logan Intl

Wed 10/15

12:00 pm-11:27 pm

2 stops12h 27m

$281

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 9/20

1:35 pm-10:39 pm

1 stop8h 04m

Boston Logan Intl

Mon 9/22

6:00 am-10:40 am

1 stop5h 40m

$282

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 9/9

5:00 am-11:29 am

1 stop5h 29m

Boston Logan Intl

Tue 9/16

6:00 am-10:40 am

1 stop5h 40m

$282

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 10/7

5:00 am-5:55 pm

2 stops11h 55m

Boston Logan Intl

Wed 10/15

4:45 pm-11:25 pm

1 stop7h 40m

$289

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 9/26

7:00 am-12:50 am

1 stop16h 50m

Boston Logan Intl

Tue 9/30

6:00 am-10:40 am

1 stop5h 40m

$290

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 9/9

7:00 am-7:19 pm

1 stop11h 19m

Boston Logan Intl

Tue 9/16

6:00 am-4:15 pm

2 stops11h 15m

$296

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 9/25

9:00 am-9:58 am

1 stop23h 58m

Boston Logan Intl

Thu 10/2

10:53 am-12:30 am

2 stops14h 37m

$297

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 9/15

2:20 pm-11:57 pm

2 stops8h 37m

Boston Logan Intl

Tue 9/23

9:05 am-10:33 pm

2 stops14h 28m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 22 results
1
2
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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 August 8, 2025.

The best time to book flights from Winnipeg to Boston is 55 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.

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 August 14, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta, 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.
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 Winnipeg to Boston. 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 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 74% 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 WestJet ($146), Air Canada ($162), and Delta ($168).

  • 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
Watertown
Hampton Beach
Waltham
Seabrook
Lowell
Lincoln
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Chelsea
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Saugus
Burlington
Braintree

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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$369FlexibilityNo cancel feeOn-time69%
DeltaCheapest$241Average$364FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$254Average$356FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$267Average$355FlexibilityNo cancel feeOn-time52%

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