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$139+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
Apr 16 — Apr 231
Wed 4/16
Wed 4/23
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 October or April, booked 55 days in advance, depart on a Saturday or Wednesday and return on a Sunday

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 April 11, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$224
(United Airlines)

One-way from

$139
(United Airlines)

Popular in

December

Cheapest in

October

Average price

$351
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.
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From Winnipeg to Boston Logan Intl
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One-way flight from Winnipeg to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($103 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 April 11, 2025.

This United Airlines deal was found by Cheapflights users on 4/10. 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 5/14:25 pmYWG - BOS
1 stop12h 14mUnited Airlines
Sat 5/106:00 amBOS - YWG
2 stops10h 31mUnited Airlines
Deal found 4/10$224
This Air Canada deal was found by Cheapflights users on 4/11. 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 9/48:00 amYWG - BOS
1 stop5h 31mAir Canada
Mon 9/156:00 amBOS - YWG
1 stop5h 40mAir Canada
Deal found 4/11$308
This Delta deal was found by Cheapflights users on 4/10. 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.
Thu 9/412:40 pmYWG - BOS
1 stop8h 45mDelta
Mon 9/157:05 amBOS - YWG
1 stop10h 53mDelta
Deal found 4/10$311
This Mytrip deal was found by Cheapflights users on 4/10. 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.
Sun 5/258:30 amYWG - BOS
3 stops23h 11mMultiple Airlines
Sun 6/17:47 pmBOS - YWG
2 stops21h 41mMultiple Airlines
Deal found 4/10$443
This Justfly.com deal was found by Cheapflights users on 4/10. 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.
Thu 5/1511:25 amYWG - BOS
1 stop5h 43mPorter Airlines
Mon 5/198:45 amBOS - YWG
2 stops10h 15mPorter Airlines
Deal found 4/10$481

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 11, 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 5/1

4:25 pm-5:39 am

1 stop12h 14m

Boston Logan Intl

Sat 5/10

6:00 am-3:31 pm

1 stop10h 31m

$224

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 9/4

8:00 am-2:31 pm

1 stop5h 31m

Boston Logan Intl

Mon 9/15

6:00 am-10:40 am

1 stop5h 40m

$308

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 9/4

12:40 pm-10:25 pm

1 stop8h 45m

Boston Logan Intl

Mon 9/15

7:05 am-4:58 pm

1 stop10h 53m

$311

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 5/25

8:30 am-8:41 am

3 stops23h 11m

Boston Logan Intl

Sun 6/1

7:47 pm-4:28 pm

2 stops21h 41m

$443

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 5/15

11:25 am-6:08 pm

1 stop5h 43m

Boston Logan Intl

Mon 5/19

8:45 am-6:00 pm

2 stops10h 15m

$481

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 5/25

4:25 pm-12:02 pm

1 stop18h 37m

$139

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 7/29

8:00 am-2:35 pm

1 stop5h 35m

$146

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 7/29

8:50 am-11:33 pm

2 stops13h 43m

$151

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 5/25

12:30 pm-7:40 am

3 stops18h 10m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

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*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
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 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 4, 2025.

The best time to book flights from Winnipeg to Boston is 55 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, January is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $218). Flying from Winnipeg to Boston in July is currently the most expensive (average of $311). 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.

What is the cheapest time of day to fly from YWG to BOS?

Find hourly flight availability from Winnipeg to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 11, 2025.

It’s typically best to fly out from Winnipeg to Boston in the morning. Doing so could potentially save you 21% on the flight price compared to flying at noon, which is usually more expensive.

Rainfall in Boston by month

Plan your trip to Boston by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.

Temperature in Boston by month

Plan your trip to Boston by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 11, 2025.
Porter Airlines
8.0
Very good
280 reviews

Crew

8.7

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Porter Airlines
8.0
Very good
280 reviews
Porter Airlines
8.0
Very good
280 reviews

Crew

8.7

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Delta
8.0
Very good
7,910 reviews
Porter Airlines
8.0
Very good
280 reviews

Crew

8.7

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
United Airlines
7.4
Good
8,636 reviews
Porter Airlines
8.0
Very good
280 reviews

Crew

8.7

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Air Canada
7.0
Good
9,088 reviews
Porter Airlines
8.0
Very good
280 reviews

Crew

8.7

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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 ($224), Air Canada ($308), and Delta ($311) offers the cheapest pricing from Winnipeg to Boston. United Airlines is 46% 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 United Airlines ($139), Air Canada ($146), and Delta ($151).

  • 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, January is the cheapest month in which you can book a flight from Winnipeg to Boston (average of $218). Flying from Winnipeg to Boston in July is currently the most expensive (average of $311). 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 Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Marlborough
Warwick
Waltham
Cambridge
Framingham
Chestnut Hill
Seekonk
Randolph
Brockton
Lowell
West Yarmouth
Woburn
Somerville
Saco
Seabrook
Burlington
Smithfield
Salem
Chelsea
Brookline

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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 2 airlines flying from Winnipeg to Boston

Discover the top 2 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$254Average$435FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$267Average$355FlexibilityNo cancel feeOn-time52%

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