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$164+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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 4/138:00 am
YWG
-
BOS
1 stop14h 59m
Multiple Airlines
Tue 4/215:40 am
BOS
-
YWG
2 stops19h 59m
Multiple Airlines
Deal found 1/20$338
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/168:00 am
YWG
-
BOS
1 stop25h 26m
Multiple Airlines
Mon 2/232:23 pm
BOS
-
YWG
2 stops22h 09m
Multiple Airlines
Deal found 1/20$354
This Air Canada deal was found by Cheapflights users on 1/20. 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 2/165:30 am
YWG
-
BOS
1 stop5h 42m
Air Canada
Mon 2/236:55 pm
BOS
-
YWG
1 stop15h 49m
Air Canada
Deal found 1/20$359
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Wed 5/66:30 am
YWG
-
BOS
1 stop10h 10m
WestJet
Mon 5/116:25 pm
BOS
-
YWG
1 stop16h 35m
WestJet
Deal found 1/20$368
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/178:00 am
YWG
-
BOS
1 stop13h 01m
Multiple Airlines
Mon 2/232:23 pm
BOS
-
YWG
2 stops22h 09m
Multiple Airlines
Deal found 1/20$369
This Air Canada deal was found by Cheapflights users on 1/19. 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 2/137:20 pm
YWG
-
BOS
1 stop15h 52m
Air Canada
Sun 2/155:30 am
BOS
-
YWG
1 stop5h 45m
Air Canada
Deal found 1/19$376
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 3/28:00 am
YWG
-
BOS
1 stop32h 15m
Multiple Airlines
Fri 3/66:00 am
BOS
-
YWG
1 stop10h 09m
Multiple Airlines
Deal found 1/19$385
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Wed 5/66:30 am
YWG
-
BOS
1 stop10h 10m
Multiple Airlines
Mon 5/115:55 pm
BOS
-
YWG
3 stops31h 35m
Multiple Airlines
Deal found 1/20$399

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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$338
(Kiwi.com)

One-way from

$164
(oojo)

Popular in

January

Cheapest in

June

Average price

$550
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 ($95 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 21, 2026.
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 4/13

8:00 am-11:59 pm

1 stop14h 59m

Boston Logan Intl

Tue 4/21

5:40 am-12:39 am

2 stops19h 59m

$338

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 2/17

8:15 am-2:52 pm

1 stop5h 37m

Boston Logan Intl

Mon 2/23

6:55 pm-9:44 am

1 stop15h 49m

$354

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 2/16

8:00 am-10:26 am

1 stop25h 26m

Boston Logan Intl

Mon 2/23

2:23 pm-11:32 am

2 stops22h 09m

$354

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 2/16

5:30 am-12:12 pm

1 stop5h 42m

Boston Logan Intl

Mon 2/23

6:55 pm-9:44 am

1 stop15h 49m

$359

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 5/6

6:30 am-5:40 pm

1 stop10h 10m

Boston Logan Intl

Mon 5/11

6:25 pm-10:00 am

1 stop16h 35m

$368

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 2/17

8:00 am-10:01 pm

1 stop13h 01m

Boston Logan Intl

Mon 2/23

2:23 pm-11:32 am

2 stops22h 09m

$369

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 2/13

7:20 pm-12:12 pm

1 stop15h 52m

Boston Logan Intl

Sun 2/15

5:30 am-10:15 am

1 stop5h 45m

$376

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 5/6

7:00 am-11:59 pm

3 stops15h 59m

Boston Logan Intl

Mon 5/11

5:55 pm-12:30 am

3 stops31h 35m

$378

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 2/16

8:00 am-10:26 am

1 stop25h 26m

Boston Logan Intl

Sun 2/22

6:55 pm-12:40 am

2 stops30h 45m

$416

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 5/27

6:30 am-5:40 pm

1 stop10h 10m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 15 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Expedia the most. Expedia 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 January 16, 2026.

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 $157). Flying from Winnipeg to Boston in January is currently the most expensive (average of $426). 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 January 21, 2026.
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
8,088 reviews

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.2

Boarding

8.1

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
8,088 reviews
Delta
7.9
Good
8,088 reviews

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.2

Boarding

8.1

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
9,191 reviews
Delta
7.9
Good
8,088 reviews

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.2

Boarding

8.1

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
10,646 reviews
Delta
7.9
Good
8,088 reviews

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.2

Boarding

8.1

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 $354, Air Canada can have you in Boston from Winnipeg in 5h 37m. 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 76% 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 Delta ($144), Air Canada ($146), and United Airlines ($171).

  • 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 $157). Flying from Winnipeg to Boston in January is currently the most expensive (average of $426). 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
Seekonk
Brockton
Warwick
Seabrook
Cranston
Lincoln
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell
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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$369FlexibilityNo cancel feeOn-time69%
DeltaCheapest$182Average$605FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$212Average$415FlexibilityNo cancel feeOn-time67%

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