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$177+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Apr 27 — May 41
Mon 4/27
Mon 5/4
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 March 28, 2026.

This Justfly.com deal was found by Cheapflights users on 3/24. 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 Justfly.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
Wed 6/1010:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 3/24$235
This FlightHub deal was found by Cheapflights users on 3/24. 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.
Tue 6/29:20 am
YWG
-
BOS
2 stops10h 35m
Porter Airlines
Tue 6/910:05 am
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 3/24$242
This United Airlines deal was found by Cheapflights users on 3/24. 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.
Fri 5/297:00 am
YWG
-
BOS
1 stop16h 59m
United Airlines
Tue 6/28:15 am
BOS
-
YWG
1 stop15h 18m
United Airlines
Deal found 3/24$252
This Delta deal was found by Cheapflights users on 3/24. 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.
Mon 6/15:41 pm
YWG
-
BOS
1 stop5h 13m
Delta
Tue 6/95:55 am
BOS
-
YWG
1 stop10h 09m
Delta
Deal found 3/24$253
This FlightHub deal was found by Cheapflights users on 3/25. 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 6/107:10 am
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Deal found 3/25$262
This Air Canada deal was found by Cheapflights users on 3/24. 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 6/25:10 am
YWG
-
BOS
1 stop5h 36m
Air Canada
Tue 6/95:10 am
BOS
-
YWG
1 stop6h 58m
Air Canada
Deal found 3/24$263
This FlightHub deal was found by Cheapflights users on 3/24. 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
Tue 6/910:05 am
BOS
-
YWG
2 stops8h 53m
Porter Airlines
Deal found 3/24$274

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 March 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$235
(Justfly.com)

One-way from

$177
(United Airlines)

Popular in

January

Cheapest in

June

Average price

$554
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. 22% potential increase in price ($139 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 28, 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

Fri 5/29

7:00 am-12:59 am

1 stop16h 59m

Boston Logan Intl

Tue 6/2

8:15 am-10:33 pm

1 stop15h 18m

$252

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 5/4

5:20 pm-11:35 pm

1 stop5h 15m

Boston Logan Intl

Thu 5/7

8:10 am-2:55 pm

1 stop7h 45m

$299

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 5/29

7:20 pm-9:54 am

1 stop13h 34m

Boston Logan Intl

Tue 6/2

5:10 am-11:08 am

1 stop6h 58m

$299

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 5/1

5:20 pm-11:35 pm

1 stop5h 15m

Boston Logan Intl

Thu 5/7

8:10 am-2:55 pm

1 stop7h 45m

$328
Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 5/10

5:41 pm-11:54 pm

1 stop5h 13m

Boston Logan Intl

Sun 5/17

5:51 am-10:54 am

1 stop6h 03m

$328

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 5/8

6:40 am-5:10 pm

1 stop9h 30m

Boston Logan Intl

Fri 5/15

5:51 am-10:54 am

1 stop6h 03m

$329

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 6/1

7:00 am-11:59 pm

2 stops15h 59m

Boston Logan Intl

Tue 6/9

5:45 am-10:33 pm

2 stops17h 48m

$335

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 6/2

5:41 pm-11:54 pm

1 stop5h 13m

Boston Logan Intl

Tue 6/9

5:55 am-3:04 pm

1 stop10h 09m

$335

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 6/1

9:20 am-5:35 pm

1 stop7h 15m

Boston Logan Intl

Wed 6/10

10:05 am-5:58 pm

2 stops8h 53m

$336

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 6/1

3:15 pm-10:39 pm

1 stop6h 24m

Boston Logan Intl

Wed 6/10

5:00 pm-11:18 pm

1 stop7h 18m

$345

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

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 March.
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 March 13, 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 $155). 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 March 28, 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
8,343 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Food

7.2

Boarding

8.1

Entertainment

7.8

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
8,343 reviews
Delta
7.9
Good
8,343 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Food

7.2

Boarding

8.1

Entertainment

7.8

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
9,493 reviews
Delta
7.9
Good
8,343 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Food

7.2

Boarding

8.1

Entertainment

7.8

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
10,848 reviews
Delta
7.9
Good
8,343 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Food

7.2

Boarding

8.1

Entertainment

7.8

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 $299, United Airlines can have you in Boston from Winnipeg in 5h 15m. 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 78% 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 $155). 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
Seabrook
Cranston
Chelsea
Lincoln
Warwick
Peabody
Waltham
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Lowell

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 March 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$423FlexibilityNo cancel feeOn-time69%
DeltaCheapest$182Average$518FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$212Average$435FlexibilityNo cancel feeOn-time67%

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