HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boston

$130+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
feb. 9 — feb. 161
dom. 2/9
dom. 2/16
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to Boston with Cheapflights

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”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 febrero 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$264
(Air Canada)

One-way from

$130
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$459
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. 15% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

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 febrero 4, 2025.

This Air Canada deal was found by Cheapflights users on 2/3. 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.
mié. 3/57:45 amYWG - BOS
1 stop8h 08mAir Canada
mar. 3/1110:50 amBOS - YWG
1 stop6h 38mAir Canada
Deal found 2/3$264
This Mytrip deal was found by Cheapflights users on 2/3. 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.
mié. 3/54:25 pmYWG - BOS
3 stops17h 55mMultiple Airlines
mar. 3/118:35 pmBOS - YWG
3 stops24h 00mMultiple Airlines
Deal found 2/3$272
This Delta deal was found by Cheapflights users on 2/3. 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.
mié. 3/512:45 pmYWG - BOS
1 stop10h 11mDelta
mar. 3/115:30 amBOS - YWG
2 stops12h 23mDelta
Deal found 2/3$278
This United Airlines deal was found by Cheapflights users on 2/2. 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.
jue. 3/611:55 amYWG - BOS
1 stop5h 47mUnited Airlines
mié. 3/128:43 pmBOS - YWG
1 stop17h 44mUnited Airlines
Deal found 2/2$281
This Porter Airlines deal was found by Cheapflights users on 2/4. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/111:45 amYWG - BOS
2 stops9h 16mPorter Airlines
lun. 6/99:45 amBOS - YWG
2 stops9h 15mPorter Airlines
Deal found 2/4$520
This Kissandfly.com deal was found by Cheapflights users on 2/2. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/610:00 amYWG - BOS
3 stops23h 49mWestJet
mié. 3/126:15 pmBOS - YWG
2 stops22h 20mWestJet
Deal found 2/2$546

Find flights from Winnipeg to Boston within your budget

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 febrero 4, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mié. 3/5

7:45 am-4:53 pm

1 stop8h 08m

Boston Logan Intl

mar. 3/11

10:50 am-4:28 pm

1 stop6h 38m

$264

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mié. 3/5

4:25 pm-11:20 am

3 stops17h 55m

Boston Logan Intl

mar. 3/11

8:35 pm-7:35 pm

3 stops24h 00m

$272

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mié. 3/5

12:45 pm-11:56 pm

1 stop10h 11m

Boston Logan Intl

mar. 3/11

5:30 am-4:53 pm

2 stops12h 23m

$278

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

jue. 3/6

11:55 am-6:42 pm

1 stop5h 47m

Boston Logan Intl

mié. 3/12

8:43 pm-1:27 pm

1 stop17h 44m

$281

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

dom. 6/1

11:45 am-10:01 pm

2 stops9h 16m

Boston Logan Intl

lun. 6/9

9:45 am-6:00 pm

2 stops9h 15m

$520

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

jue. 3/6

10:00 am-10:49 am

3 stops23h 49m

Boston Logan Intl

mié. 3/12

6:15 pm-3:35 pm

2 stops22h 20m

$546

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mié. 5/14

9:00 am-5:34 pm

1 stop7h 34m

$130

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

dom. 7/27

5:00 am-11:28 am

1 stop5h 28m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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.

Travel insights for flights from Winnipeg to Boston

Get recent, data-driven insights about flights from Winnipeg to Boston including ideal travel times, pricing trends, and more.

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 31, 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 febrero 4, 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 febrero 4, 2025.
Delta
8.0
Very good
8,415 reviews

Boarding

8.2

Comfort

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,415 reviews
Delta
8.0
Very good
8,415 reviews

Boarding

8.2

Comfort

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
8,415 reviews

Boarding

8.2

Comfort

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,890 reviews
Delta
8.0
Very good
8,415 reviews

Boarding

8.2

Comfort

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.2
Good
2,814 reviews
Delta
8.0
Very good
8,415 reviews

Boarding

8.2

Comfort

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Canada
7.0
Good
8,666 reviews
Delta
8.0
Very good
8,415 reviews

Boarding

8.2

Comfort

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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, Air Canada ($264), Delta ($278), and United Airlines ($281) offers the cheapest pricing from Winnipeg to Boston. Air Canada is 40% 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, 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
Warwick
Sturbridge
Marlborough
Waltham
Brockton
Cambridge
Framingham
Somerville
Chestnut Hill
Seekonk
Randolph
Lowell
Watertown
West Yarmouth
Woburn
Saco
Seabrook
Salem
Brookline
Fall River

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 febrero 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$254Average$507FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$267Average$355FlexibilityNo cancel feeOn-time52%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.