$166 Cheap Flights from Boston (BOS) to Winnipeg (YWG)

View $166 flight on Thu, Jan 8, 2026Opens in a new window

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

Cheap Flights from Boston to Winnipeg (BOS-YWG)

Prices were available within the past 7 days and start at $166 for one-way flights and $380 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, Jan 8 - Tue, Jan 20
BOS
Boston
YWG
Winnipeg
$380 Roundtrip, found 1 hour ago
$380
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Thu, Jan 8 from Boston to Winnipeg, returning Tue, Jan 20, priced at $380 found 1 hour ago
Air Canada
Thu, Jan 8 - Tue, Jan 20
BOS
Boston
YWG
Winnipeg
$387 Roundtrip, found 1 hour ago
$387
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Thu, Jan 8 from Boston to Winnipeg, returning Tue, Jan 20, priced at $387 found 1 hour ago
Air Canada
Thu, Jan 8 - Tue, Jan 20
BOS
Boston
YWG
Winnipeg
$393 Roundtrip, found 1 hour ago
$393
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Thu, Jan 8 from Boston to Winnipeg, returning Tue, Jan 20, priced at $393 found 1 hour ago
Delta
Fri, Dec 5 - Tue, Dec 9
BOS
Boston
YWG
Winnipeg
$398 Roundtrip, found 3 days ago
$398
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 5 from Boston to Winnipeg, returning Tue, Dec 9, priced at $398 found 3 days ago
Air Canada
Fri, Dec 5 - Tue, Dec 9
BOS
Boston
YWG
Winnipeg
$404 Roundtrip, found 3 days ago
$404
Roundtrip
found 3 days ago
Select Air Canada flight, departing Fri, Dec 5 from Boston to Winnipeg, returning Tue, Dec 9, priced at $404 found 3 days ago
Air Canada
Fri, Dec 5 - Tue, Dec 9
BOS
Boston
YWG
Winnipeg
$406 Roundtrip, found 3 days ago
$406
Roundtrip
found 3 days ago
Select Air Canada flight, departing Fri, Dec 5 from Boston to Winnipeg, returning Tue, Dec 9, priced at $406 found 3 days ago
Air Canada
Thu, Jan 8 - Tue, Jan 20
BOS
Boston
YWG
Winnipeg
$410 Roundtrip, found 1 hour ago
$410
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Thu, Jan 8 from Boston to Winnipeg, returning Tue, Jan 20, priced at $410 found 1 hour ago
United
Thu, Jan 8 - Tue, Jan 20
BOS
Boston
YWG
Winnipeg
$421 Roundtrip, found 1 hour ago
$421
Roundtrip
found 1 hour ago
Select United flight, departing Thu, Jan 8 from Boston to Winnipeg, returning Tue, Jan 20, priced at $421 found 1 hour ago
Porter Airlines
Mon, Aug 24 - Fri, Aug 28
BOS
Boston
YWG
Winnipeg
$552 Roundtrip, found 8 hours ago
$552
Roundtrip
found 8 hours ago
Select Porter Airlines flight, departing Mon, Aug 24 from Boston to Winnipeg, returning Fri, Aug 28, priced at $552 found 8 hours ago
WestJet
Wed, Nov 12 - Thu, Nov 13
BOS
Boston
YWG
Winnipeg
$904 Roundtrip, found 3 days ago
$904
Roundtrip
found 3 days ago
Select WestJet flight, departing Wed, Nov 12 from Boston to Winnipeg, returning Thu, Nov 13, priced at $904 found 3 days ago

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

May is typically the cheapest month to fly

From $229 - $717 per traveler.

Alternative airports near Winnipeg

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

Select flight to Winnipeg Intl. YWG. Cheapest and Closest option available. Average driving time to city center is 15 minutes. Flights from $1,034
YWG
Winnipeg Intl.
CheapestClosest
Average driving time to city center15 min
Flights from $1,034
Flights from Boston (BOS) to Winnipeg (YWG)
Origin airport
Logan Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Airlines serving
Air Canada, Delta, Porter Airlines, United, WestJet
Roundtrip price
$380
Distance
1349 mi

Boston to Winnipeg Flights

The cheapest times to fly from Boston to Winnipeg

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 Boston to Winnipeg are during the month of January. You can find some of the cheapest flights from Boston to Winnipeg with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Boston to Winnipeg

Sunday is one of the best days to book for cheap flights from Boston to Winnipeg: 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 Boston to Winnipeg

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 Boston to Winnipeg in 2025. You can also book with separate airlines for your outbound and return journeys, from $166 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 Boston to Winnipeg 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 Boston to Winnipeg 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 Logan Intl. Airport (BOS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) cost?
Get a cheap one-way flight from $166 or cheap return flight from $380 from Logan Intl. Airport (BOS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) 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 Logan Intl. Airport (BOS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Traveling in January is a great way to save, as it's the cheapest month for flights between BOS and YWG. You'll usually find the lowest prices during off-peak months.
What is the cheapest airline that flies from Logan Intl. Airport (BOS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest BOS to YWG flight.
How many flights per day from Logan Intl. Airport (BOS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
You'll have to take a flight with a layover if you're traveling from Logan Intl. Airport (BOS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from BOS to YWG?
You'll usually 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 Logan Intl. Airport (BOS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Book a flight from Logan Intl. Airport (BOS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) that takes off before 3 PM to reduce the risk of delays and cancellations. Later departures have a 22% higher chance of being canceled, on average.**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 Logan Intl. Airport (BOS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) last-minute?
Last-minute fares from BOS to YWG are typically more expensive. To secure the lowest rates, start searching for flights ahead of time. That being said, if you're flexible with your travel dates, it's possible to find a cheap ticket just before your departure.
Is it cheaper to book a BOS to YWG flight and hotel package?
Opting for a BOS to YWG flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Pick from our impressive range of hotels and then add flights, car rentals and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Logan Intl. Airport (BOS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
In most instances, you can cancel or reschedule your BOS to YWG flight. However, there may be additional fees, especially if you booked more than 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you want more details, head to our Customer Service portal.

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*Available to One Key members.