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$156+ 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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Boston Logan Intl are usually found in October or May, 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 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$280
(Delta)

One-way from

$156
(United Airlines)

Popular in

December

Cheapest in

October

Average price

$354
Provider with most accurate pricing for Winnipeg-Boston Logan Intl flight deals.
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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
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Highest demand for flights based on searches. 20% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($20 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 30, 2025.

This Delta deal was found by Cheapflights users on 4/28. 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 7/1012:26 pmYWG - BOS
2 stops10h 27mDelta
Wed 8/65:35 amBOS - YWG
1 stop6h 56mDelta
Deal found 4/28$280
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 5/212:20 pmYWG - BOS
2 stops8h 39mUnited Airlines
Tue 5/276:00 amBOS - YWG
1 stop10h 31mUnited Airlines
Deal found 4/28$288
This Air Canada deal was found by Cheapflights users on 4/29. 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 7/105:00 amYWG - BOS
1 stop5h 28mAir Canada
Wed 8/610:40 amBOS - YWG
1 stop7h 58mAir Canada
Deal found 4/29$299
This Mytrip deal was found by Cheapflights users on 4/28. 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.
Fri 7/2511:45 amYWG - BOS
2 stops9h 16mPorter Airlines
Fri 8/13:50 pmBOS - YWG
1 stop7h 56mPorter Airlines
Deal found 4/28$355
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 6/711:45 amYWG - BOS
2 stops20h 24mMultiple Airlines
Wed 6/113:50 pmBOS - YWG
1 stop7h 56mMultiple Airlines
Deal found 4/28$385

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 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 7/10

12:26 pm-11:53 pm

2 stops10h 27m

Boston Logan Intl

Wed 8/6

5:35 am-11:31 am

1 stop6h 56m

$280

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 5/21

2:20 pm-11:59 pm

2 stops8h 39m

Boston Logan Intl

Tue 5/27

6:00 am-3:31 pm

1 stop10h 31m

$288

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 7/10

5:00 am-11:28 am

1 stop5h 28m

Boston Logan Intl

Wed 8/6

10:40 am-5:38 pm

1 stop7h 58m

$299

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 7/25

11:45 am-10:01 pm

2 stops9h 16m

Boston Logan Intl

Fri 8/1

3:50 pm-10:46 pm

1 stop7h 56m

$355

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 6/7

11:45 am-9:09 am

2 stops20h 24m

Boston Logan Intl

Wed 6/11

3:50 pm-10:46 pm

1 stop7h 56m

$385

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 6/12

2:20 pm-12:59 am

1 stop9h 39m

$156

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 9/1

8:00 am-2:31 pm

1 stop5h 31m

$171

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 9/1

12:40 pm-1:06 am

2 stops11h 26m

$183

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 9/11

9:00 am-11:29 pm

2 stops13h 29m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

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*2 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 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 April 25, 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 30, 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 30, 2025.
Porter Airlines
8.0
Very good
285 reviews

Comfort

8.1

Crew

8.8

Entertainment

7.0

Overall

8.0

Boarding

8.2

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews

Comfort

8.1

Crew

8.8

Entertainment

7.0

Overall

8.0

Boarding

8.2

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,929 reviews
Porter Airlines
8.0
Very good
285 reviews

Comfort

8.1

Crew

8.8

Entertainment

7.0

Overall

8.0

Boarding

8.2

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,696 reviews
Porter Airlines
8.0
Very good
285 reviews

Comfort

8.1

Crew

8.8

Entertainment

7.0

Overall

8.0

Boarding

8.2

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,244 reviews
Porter Airlines
8.0
Very good
285 reviews

Comfort

8.1

Crew

8.8

Entertainment

7.0

Overall

8.0

Boarding

8.2

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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, Delta ($280), United Airlines ($288), and Air Canada ($299) offers the cheapest pricing from Winnipeg to Boston. Delta is 32% 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 ($156), Air Canada ($171), and Delta ($183).

  • 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
Cambridge
Waltham
Framingham
Chestnut Hill
Randolph
Brockton
Lowell
Woburn
Somerville
York Beach
Saco
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Chelsea
Seabrook

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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$331FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$254Average$422FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$267Average$355FlexibilityNo cancel feeOn-time52%

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