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$183+ 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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
May 10 — May 171
Sun 5/10
Sun 5/17
1 adult, Economy
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Cheap 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 April 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/8. 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.
Tue 6/29:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Tue 6/910:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 4/8$296
This FlightHub deal was found by Cheapflights users on 4/8. 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.
Mon 6/19:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Wed 6/1010:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 4/8$303
This United Airlines deal was found by Cheapflights users on 4/6. 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.
Tue 6/28:45 am
YWG
-
BOS
2 stops15h 14m
United Airlines
Tue 6/910:55 am
BOS
-
YWG
1 stop12h 38m
United Airlines
Deal found 4/6$306
This Air Canada deal was found by Cheapflights users on 4/6. 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 6/28:10 am
YWG
-
BOS
1 stop6h 58m
Air Canada
Tue 6/95:10 am
BOS
-
YWG
1 stop6h 58m
Air Canada
Deal found 4/6$316
This Air Canada deal was found by Cheapflights users on 4/6. 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.
Mon 6/13:15 pm
YWG
-
BOS
1 stop6h 24m
Air Canada
Wed 6/35:50 am
BOS
-
YWG
1 stop7h 14m
Air Canada
Deal found 4/6$327
This Porter Airlines deal was found by Cheapflights users on 4/7. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Sat 5/307:10 am
BOS
-
YWG
2 stops11h 53m
Porter Airlines
Deal found 4/7$332
This FlightHub deal was found by Cheapflights users on 4/6. 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 7/99:20 am
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Fri 7/1010:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 4/6$333

Find 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 April 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$293
(Trip.com)

One-way from

$183
(Air Canada)

Popular in

April

Cheapest in

June

Average price

$788
Provider with most accurate pricing for Winnipeg-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Boston Logan Intl flights.
Search Deals
From Winnipeg to Boston Logan Intl
Search Deals
One-way flight from Winnipeg to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($111 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 April 10, 2026.
Use the filters below to find and compare flights from Winnipeg to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 6/2

8:45 am-12:59 am

2 stops15h 14m

Boston Logan Intl

Tue 6/9

10:55 am-10:33 pm

1 stop12h 38m

$306

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 6/2

9:20 am-8:55 pm

2 stops10h 35m

Boston Logan Intl

Tue 6/9

10:05 am-3:19 pm

1 stop6h 14m

$309

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 6/2

8:10 am-4:08 pm

1 stop6h 58m

Boston Logan Intl

Tue 6/9

5:10 am-11:08 am

1 stop6h 58m

$316
Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 6/1

3:15 pm-10:39 pm

1 stop6h 24m

Boston Logan Intl

Wed 6/3

5:50 am-12:04 pm

1 stop7h 14m

$327

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 5/26

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Sat 5/30

7:10 am-6:03 pm

2 stops11h 53m

$332

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 6/1

5:10 am-2:47 pm

2 stops8h 37m

Boston Logan Intl

Wed 6/10

5:10 am-11:08 am

1 stop6h 58m

$335

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 6/2

3:50 pm-11:54 pm

1 stop7h 04m

Boston Logan Intl

Tue 6/9

5:55 am-3:04 pm

1 stop10h 09m

$338
Cheapest one-way

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 5/21

3:15 pm-10:39 pm

1 stop6h 24m

$183

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 5/23

8:45 am-10:20 am

2 stops24h 35m

$194
Quickest one-way

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 5/24

5:41 pm-11:54 pm

1 stop5h 13m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/6

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Compare providers for flights from Winnipeg to Boston

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 Winnipeg to Boston in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 Winnipeg-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-Boston flights, Cheapflights users trust FlightHub the most. FlightHub 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 Winnipeg-Boston 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 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 April 10, 2026.

The best time to book flights from Winnipeg to Boston is 16 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, May is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $150). Flying from Winnipeg to Boston in January is currently the most expensive (average of $782). 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 April 10, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAir Canada 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
7.9
Good
8,404 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

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
8,404 reviews
Delta
7.9
Good
8,404 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

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
9,567 reviews
Delta
7.9
Good
8,404 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

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
10,915 reviews
Delta
7.9
Good
8,404 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

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 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 $311, Porter Airlines can have you in Boston from Winnipeg in 6h 24m. 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 ($182), and Air Canada ($212) offers the cheapest pricing from Winnipeg to Boston. United Airlines is 80% cheaper than the average price of flights available within the next 90 days to this destination.

  • 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, May is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $150). Flying from Winnipeg to Boston in January is currently the most expensive (average of $782). 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
Medford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Cranston
Chelsea
Seabrook
Warwick
Peabody
York Beach
Londonderry
Swansea
Old Orchard Beach
Lincoln
Quincy
Waltham
Lowell

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Winnipeg to Boston

Discover the top 3 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 April 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$423FlexibilityNo cancel feeOn-time69%
DeltaCheapest$182Average$605FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$212Average$435FlexibilityNo cancel feeOn-time67%

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