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$249+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Winnipeg to Boston Logan Intl are usually found in June or August, booked 24 days in advance, depart on a Saturday or Wednesday and return on a Sunday

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 October 30, 2025.

This Air Canada deal was found by Cheapflights users on 10/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/245:30 amYWG - BOS
1 stop9h 27mAir Canada
Tue 12/25:30 amBOS - YWG
1 stop5h 46mAir Canada
Deal found 10/29$338
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/277:30 amYWG - BOS
2 stops16h 14mMultiple Airlines
Tue 12/212:44 pmBOS - YWG
1 stop27h 23mMultiple Airlines
Deal found 10/29$383
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/278:20 pmYWG - BOS
1 stop12h 15mMultiple Airlines
Thu 12/47:00 amBOS - YWG
1 stop13h 35mMultiple Airlines
Deal found 10/29$392
This Air Canada deal was found by Cheapflights users on 10/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/278:15 amYWG - BOS
1 stop5h 37mAir Canada
Tue 12/210:15 amBOS - YWG
1 stop7h 20mAir Canada
Deal found 10/29$439
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 11/246:40 amYWG - BOS
2 stops12h 20mDelta
Tue 12/25:45 amBOS - YWG
1 stop7h 00mDelta
Deal found 10/29$462
This Air Canada deal was found by Cheapflights users on 10/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/217:05 pmYWG - BOS
1 stop16h 07mAir Canada
Mon 12/15:30 amBOS - YWG
2 stops12h 49mAir Canada
Deal found 10/30$497

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$338
(Air Canada)

One-way from

$249
(Delta)

Popular in

December

Cheapest in

June

Average price

$355
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 ($119 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 30, 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 11/27

7:30 am-12:44 am

2 stops16h 14m

Boston Logan Intl

Tue 12/2

12:44 pm-3:07 pm

1 stop27h 23m

$383

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 11/27

8:20 pm-9:35 am

1 stop12h 15m

Boston Logan Intl

Thu 12/4

7:00 am-7:35 pm

1 stop13h 35m

$392

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 11/27

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Tue 12/2

10:15 am-4:35 pm

1 stop7h 20m

$439

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 11/21

7:05 pm-12:12 pm

1 stop16h 07m

Boston Logan Intl

Mon 12/1

5:30 am-5:19 pm

2 stops12h 49m

$497

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 11/24

5:30 am-2:52 pm

2 stops8h 22m

Boston Logan Intl

Tue 12/2

3:40 pm-11:54 pm

2 stops9h 14m

$521

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 12/13

2:20 pm-9:45 pm

1 stop6h 25m

$249

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 12/13

12:35 pm-11:24 pm

2 stops9h 49m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Winnipeg-Boston flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 October 24, 2025.

The best time to book flights from Winnipeg to Boston is 24 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 $164). Flying from Winnipeg to Boston in December is currently the most expensive (average of $358). 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 October 30, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and Air 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
7,993 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Delta
7.9
Good
7,993 reviews
Delta
7.9
Good
7,993 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,993 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Air Canada
7.1
Good
10,376 reviews
Delta
7.9
Good
7,993 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!

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 75% 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 $164). Flying from Winnipeg to Boston in December is currently the most expensive (average of $358). 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
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$369FlexibilityNo cancel feeOn-time69%
DeltaCheapest$241Average$560FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$254Average$419FlexibilityNo cancel feeOn-time67%

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