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$148+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Jan 8 — Jan 151
Thu 1/8
Thu 1/15
1 adult, Economy
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1. Tell us where you want to go

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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

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 December 9, 2025.

This American Airlines deal was found by Cheapflights users on 12/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amYWG - BOS
2 stops15h 55mAmerican Airlines
Sat 1/32:15 pmBOS - YWG
2 stops10h 20mAmerican Airlines
Deal found 12/7$675
This United Airlines deal was found by Cheapflights users on 12/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/181:30 pmYWG - BOS
1 stop8h 07mUnited Airlines
Sat 1/32:15 pmBOS - YWG
2 stops22h 42mUnited Airlines
Deal found 12/7$693
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/188:20 pmYWG - BOS
1 stop12h 15mMultiple Airlines
Sat 1/37:05 amBOS - YWG
1 stop17h 30mMultiple Airlines
Deal found 12/7$715
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:45 pmYWG - BOS
1 stop5h 16mMultiple Airlines
Mon 12/1511:23 amBOS - YWG
2 stops33h 43mMultiple Airlines
Deal found 12/7$737
This United Airlines deal was found by Cheapflights users on 12/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/132:20 pmYWG - BOS
1 stop6h 25mUnited Airlines
Sat 12/207:36 pmBOS - YWG
2 stops17h 21mUnited Airlines
Deal found 12/7$803
This Trip.com deal was found by Cheapflights users on 12/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/812:35 pmYWG - BOS
1 stop27h 43mWestJet
Mon 12/156:24 pmBOS - YWG
1 stop18h 21mWestJet
Deal found 12/7$927
This Mytrip deal was found by Cheapflights users on 12/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:20 pmYWG - BOS
2 stops21h 46mMultiple Airlines
Sat 12/2011:55 amBOS - YWG
3 stops35h 46mMultiple Airlines
Deal found 12/7$1,146

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 December 9, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$213
(Kiwi.com)

One-way from

$148
(Kiwi.com)

Popular in

December

Cheapest in

June

Average price

$557
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. 20% potential increase in price ($106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 9, 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

Wed 1/21

7:30 am-1:03 am

1 stop16h 33m

Boston Logan Intl

Wed 1/28

6:00 am-3:07 pm

1 stop10h 07m

$213

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 1/16

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Thu 1/22

5:30 am-10:16 am

1 stop5h 46m

$299

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 2/2

8:00 am-11:57 pm

1 stop14h 57m

Boston Logan Intl

Tue 2/3

5:23 pm-3:09 pm

2 stops22h 46m

$333

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 2/5

5:00 am-8:30 pm

1 stop14h 30m

Boston Logan Intl

Mon 2/9

11:50 am-12:35 am

1 stop13h 45m

$384

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 1/22

9:00 pm-1:13 am

2 stops27h 13m

$148

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 1/23

2:40 pm-4:28 pm

3 stops24h 48m

$190

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 1/23

4:25 pm-11:05 am

2 stops17h 40m

$236

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 4/30

8:15 am-2:52 pm

1 stop5h 37m

$246

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 4/15

8:15 am-2:52 pm

1 stop5h 37m

$249

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 1/22

8:15 am-2:52 pm

1 stop5h 37m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

Showing 1-10 of 14 results
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 December.
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 December 5, 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 $161). Flying from Winnipeg to Boston in March is currently the most expensive (average of $328). 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 December 9, 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
8,009 reviews

Entertainment

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Overall

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
8,009 reviews
Delta
7.9
Good
8,009 reviews

Entertainment

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Overall

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
9,089 reviews
Delta
7.9
Good
8,009 reviews

Entertainment

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Overall

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
10,514 reviews
Delta
7.9
Good
8,009 reviews

Entertainment

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Food

7.3

Overall

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 $299, Air Canada can have you in Boston from Winnipeg in 5h 37m. Airlines will cover a distance of 1350 mi.

  • 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 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 $161). Flying from Winnipeg to Boston in March is currently the most expensive (average of $328). 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
Cranston
Lincoln
Lowell
Smithfield
Peabody
Brockton
Quincy
York Beach
Warwick
Londonderry
Swansea
Old Orchard Beach
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 December 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$301FlexibilityNo cancel feeOn-time69%
DeltaCheapest$241Average$605FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$254Average$415FlexibilityNo cancel feeOn-time67%

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