$179 Cheap Flights from Winnipeg (YWG) to Boston (BOS)

View $179 flight on Fri, Dec 5, 2025Opens in a new window

Popular airlines from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Logan International Airport (BOS)

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Cheap Flights from Winnipeg to Boston (YWG-BOS)

Prices were available within the past 7 days and start at $179 for one-way flights and $377 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Dec 15 - Wed, Dec 31
YWG
Winnipeg
BOS
Boston
$377 Roundtrip, found 3 hours ago
$377
Roundtrip
found 3 hours ago
Select Delta flight, departing Mon, Dec 15 from Winnipeg to Boston, returning Wed, Dec 31, priced at $377 found 3 hours ago
Air Canada
Tue, Dec 23 - Thu, Jan 1
YWG
Winnipeg
BOS
Boston
$420 Roundtrip, found 4 days ago
$420
Roundtrip
found 4 days ago
Select Air Canada flight, departing Tue, Dec 23 from Winnipeg to Boston, returning Thu, Jan 1, priced at $420 found 4 days ago
Air Canada
Sat, Dec 13 - Mon, Dec 29
YWG
Winnipeg
BOS
Boston
$422 Roundtrip, found 4 days ago
$422
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sat, Dec 13 from Winnipeg to Boston, returning Mon, Dec 29, priced at $422 found 4 days ago
Delta
Tue, Dec 23 - Tue, Jan 6
YWG
Winnipeg
BOS
Boston
$423 Roundtrip, found 4 days ago
$423
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Dec 23 from Winnipeg to Boston, returning Tue, Jan 6, priced at $423 found 4 days ago
Air Canada
Tue, Dec 23 - Thu, Jan 8
YWG
Winnipeg
BOS
Boston
$425 Roundtrip, found 4 days ago
$425
Roundtrip
found 4 days ago
Select Air Canada flight, departing Tue, Dec 23 from Winnipeg to Boston, returning Thu, Jan 8, priced at $425 found 4 days ago
Air Canada
Sat, Dec 6 - Thu, Dec 25
YWG
Winnipeg
BOS
Boston
$427 Roundtrip, found 4 days ago
$427
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sat, Dec 6 from Winnipeg to Boston, returning Thu, Dec 25, priced at $427 found 4 days ago
Air Canada
Wed, Dec 24 - Mon, Jan 12
YWG
Winnipeg
BOS
Boston
$427 Roundtrip, found 4 days ago
$427
Roundtrip
found 4 days ago
Select Air Canada flight, departing Wed, Dec 24 from Winnipeg to Boston, returning Mon, Jan 12, priced at $427 found 4 days ago
United
Wed, Dec 17 - Tue, Dec 30
YWG
Winnipeg
BOS
Boston
$433 Roundtrip, found 4 hours ago
$433
Roundtrip
found 4 hours ago
Select United flight, departing Wed, Dec 17 from Winnipeg to Boston, returning Tue, Dec 30, priced at $433 found 4 hours ago
Porter Airlines
Tue, May 26 - Mon, Jun 1
YWG
Winnipeg
BOS
Boston
$437 Roundtrip, found 15 hours ago
$437
Roundtrip
found 15 hours ago
Select Porter Airlines flight, departing Tue, May 26 from Winnipeg to Boston, returning Mon, Jun 1, priced at $437 found 15 hours ago
WestJet
Fri, Dec 19 - Thu, Dec 25
YWG
Winnipeg
BOS
Boston
$728 Roundtrip, found 8 hours ago
$728
Roundtrip
found 8 hours ago
Select WestJet flight, departing Fri, Dec 19 from Winnipeg to Boston, returning Thu, Dec 25, priced at $728 found 8 hours ago

Find the cheapest month to fly from Winnipeg (YWG) to Boston (BOS)

May is typically the cheapest month to fly

From $218 - $515 per traveler.

Alternative airports near Boston

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Logan Intl. BOS. Cheapest and Closest option available. Average driving time to city center is 7 minutes. Flights from $803
BOS
Logan Intl.
CheapestClosest
Average driving time to city center7 min
Flights from $803
Flights from Winnipeg (YWG) to Boston (BOS)
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
Logan Intl.
Airlines serving
Air Canada, Delta, Porter Airlines, United, WestJet
Roundtrip price
$377
Distance
1349 mi

Winnipeg to Boston Flights

The cheapest times to fly from Winnipeg to Boston

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Winnipeg to Boston are during the month of December. You can find some of the cheapest flights from Winnipeg to Boston with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Winnipeg to Boston

Sunday is one of the best days to book for cheap flights from Winnipeg to Boston: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Winnipeg to Boston

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Winnipeg to Boston in 2025. You can also book with separate airlines for your outbound and return journeys, from $179 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Winnipeg to Boston flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Winnipeg to Boston airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Logan Intl. Airport (BOS) cost?
Grab a cheap one-way flight from $179 or cheap return flight from $377 from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Logan Intl. Airport (BOS) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Logan Intl. Airport (BOS)?
Planning your getaway for December is a good way to save, as it's the cheapest month for flights between YWG and BOS. You'll often find the lowest fares during the off-season.
What is the cheapest airline that flies from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Logan Intl. Airport (BOS)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from YWG to BOS. Then, sort your results by "Price (lowest to highest)" to snap up a good deal.
How many flights per day from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Logan Intl. Airport (BOS)?
You'll need to take a flight with a layover when traveling from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Logan Intl. Airport (BOS). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from YWG to BOS?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Logan Intl. Airport (BOS)?
To land at Logan Intl. Airport (BOS) on time, book a flight that leaves Winnipeg James Armstrong Richardson Intl. Airport (YWG) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Logan Intl. Airport (BOS) last-minute?
Waiting until right before your break to book a flight from YWG to BOS often results in higher prices. While you may find some last-minute deals, they aren't always guaranteed. Be flexible with your travel plans for a better chance of landing a bargain.
Is it cheaper to book a YWG to BOS flight and hotel package?
You can save money by booking a YWG to BOS flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've chosen your ideal flights and accommodations, consider adding extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Logan Intl. Airport (BOS)?
If you booked your YWG to BOS flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more information.

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*Available to One Key members.