BOS - YWG

$149 Find Cheap Flights from Boston to Winnipeg

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Winnipeg departing on 5/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Winnipeg, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Winnipeg, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$291
Overall average: $498
Air Canada
Sat 4/25Mon 5/4
BOS - YWG • 1 stop
Cheapest one-way
$171
Typical prices: $110-$160
United Airlines
Fri 5/1
BOS - YWG • 1 stop
Top airlines
Cheapest • from $291 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Boston and Winnipeg. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $441 (round-trip)
Shortest trip • 5h 55m (one-way)
Insights
Insights
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Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 61% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 50% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Winnipeg!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Boston to Winnipeg (BOS-YWG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Winnipeg that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Winnipeg

Sat, Apr 25 - Mon, May 4
Air Canada Logo
5:30 am - 10:09 am
BOS
-
YWG
5h 39m
1 stop
Air Canada Logo
8:00 am - 2:47 pm
YWG
-
BOS
5h 47m
1 stop
$291Air Canada
Fri, May 8 - Sun, May 17
Air Canada Logo
5:10 am - 11:08 am
BOS
-
YWG
6h 58m
1 stop
Air Canada Logo
8:00 am - 2:47 pm
YWG
-
BOS
5h 47m
1 stop
$292Air Canada
Sat, Apr 25 - Mon, May 4
Air Canada Logo
6:15 am - 12:33 pm
BOS
-
YWG
7h 18m
1 stop
Air Canada Logo
5:10 am - 2:47 pm
YWG
-
BOS
8h 37m
2 stops
$299Air Canada
Fri, May 8 - Sun, May 17
Air Canada Logo
5:10 am - 11:08 am
BOS
-
YWG
6h 58m
1 stop
Air Canada Logo
5:10 am - 2:47 pm
YWG
-
BOS
8h 37m
2 stops
$301Air Canada
Sat, Apr 25 - Mon, May 4
Air Canada Logo
3:35 pm - 11:48 pm
BOS
-
YWG
9h 13m
2 stops
Air Canada Logo
5:10 am - 2:47 pm
YWG
-
BOS
8h 37m
2 stops
$304Air Canada
Tue, Jun 23 - Tue, Jun 30
Porter Airlines Logo
10:05 am - 3:19 pm
BOS
-
YWG
6h 14m
1 stop
Porter Airlines Logo
9:20 am - 5:35 pm
YWG
-
BOS
7h 15m
1 stop
$324Porter Airlines
Fri, May 8 - Sun, May 17
Air Canada Logo
5:50 am - 4:18 pm
BOS
-
YWG
11h 28m
2 stops
Air Canada Logo
5:10 am - 2:47 pm
YWG
-
BOS
8h 37m
2 stops
$332Air Canada
Sat, May 2 - Sat, May 9
Air Canada Logo
10:35 am - 3:14 pm
BOS
-
YWG
5h 39m
1 stop
Air Canada Logo
5:10 am - 11:46 am
YWG
-
BOS
5h 36m
1 stop
$341Air Canada
Mon, May 4 - Mon, May 11
Air Canada Logo
10:35 am - 3:14 pm
BOS
-
YWG
5h 39m
1 stop
Air Canada Logo
11:00 am - 6:07 pm
YWG
-
BOS
6h 07m
1 stop
$345Air Canada
Sat, May 2 - Sat, May 9
Air Canada Logo
10:35 am - 3:14 pm
BOS
-
YWG
5h 39m
1 stop
Air Canada Logo
8:10 am - 9:27 pm
YWG
-
BOS
12h 17m
2 stops
$346Air Canada
Booking Insights

KAYAK's insights & trends for Boston to Winnipeg flights

Get data-powered insights and trends into flights from Boston to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Boston to Winnipeg?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Winnipeg, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to Winnipeg is May, where tickets cost $256 (return) on average. On the other hand, the most expensive months are January and February, where the average cost of round-trip tickets is $774 and $649 respectively.

How far in advance should I book a flight from Boston to Winnipeg?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Winnipeg, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Winnipeg, you should book around 4 weeks before departure, which saves you about 61% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonApril
Cheapest flight$171
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Boston to Winnipeg

When to book flights from Boston to Winnipeg

Are your dates flexible? Find out the best times to travel from Boston to Winnipeg based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Boston to Winnipeg

  • What is the cheapest flight from Boston to Winnipeg?

    In the last 3 days, the lowest price for a flight from Boston to Winnipeg was $149 for a one-way ticket and $291 for a round-trip.

  • Do I need a passport to fly between Boston and Winnipeg?

    Yes

  • Which airports will I be using when flying from Boston to Winnipeg?

    When flying out of Boston you will be using Boston Logan Intl. You will be landing at Winnipeg, also known as Winnipeg.

  • Which aircraft models fly most regularly from Boston to Winnipeg?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Boston to Winnipeg?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Boston and Winnipeg, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Boston to Winnipeg, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Boston to Winnipeg are Delta and United Airlines. With an average price for the route of $420 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $642 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Boston to Winnipeg?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Winnipeg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Winnipeg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Boston is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Winnipeg?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Boston with another airline. Booking your flights between Boston and YWG can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Winnipeg?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Boston to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Boston to Winnipeg. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston to Winnipeg? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8313 reviews
8.5Crew
8.1Boarding
7.2Food
7.9Comfort
7.8Entertainment
Airline reviews

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

2.0 MediocreAnonymous, Mar 2026
HNL - ATL
Read more Delta reviews

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

It’s always a great time flying with united airlines.

Entertainment kept turning itself off. Gave up on watching a movie.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

Not United Airlines' fault. It's ORL airport's fault.

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Departed Palm Springs over an hour late because there’s only one gate, and it has always delayed by the arriving and departing flight to Toronto and the arriving flight from Vancouver.

I checked a bag and there was only one agent to assist all customers with any issues.

I want to thank Carlos at the Miami AC desk - he was amazing and went over and above to help us out. Thank you Carlos and all the best to you!!! You made our faith in AC feel great! Sincerely, David Cubitt

Flight was canceled due to mechanical issues. After a considerable wait in the queue, Air Canada customer service was very helpful to get us on another flight. I am disappointed to report our rescheduled flight is for three days from now. Three days of extra expenses and inconvenience is unacceptable.

Extremely disappointing. My original Denver–Vancouver–Bangkok itinerary was cancelled due to a crewing issue. I was not proactively supported and had to drive back home after already reaching the airport. Communication was poor throughout, and attempts to contact customer service resulted in being on hold for nearly three hours without reaching anyone. Instead of being rebooked on the same direct routing the following day, I was rerouted onto a much longer itinerary via multiple cities and airlines, which resulted in arriving approximately 30 hours later than scheduled. At Denver airport, there was no visible Air Canada representative available to properly assist. Ground staff offered no real support beyond directing passengers to a phone number. There was no clear communication, no ownership, and no meaningful customer care during a major disruption. The final journey involved three flights instead of the original two, significantly increasing travel time and stress. Overall, the handling of the cancellation and lack of customer support was unacceptable. What could have been better? Clear communication during the cancellation Accessible customer service (phone support that actually answers) Proper in-person assistance at the airport Rebooking onto a comparable routing rather than a significantly longer one

Great setup on both flights except the last flight we got condensed dripping all over me in the last 20 mins of the flight

The last 3 hours it was freezing cold in row 56. Multiple people had their winter coats on and were utilizing the blankets provided by the airline. I also did not have easy access to figure out how to book my food allergy and advance for my meals. Most of everything I received was something I couldn't eat. This needs to be made more accessible. Also, I'm 5'10 which is the average height of the American male. I flew from Philadelphia to Toronto and then to Tokyo and the seats were absolutely unbearable. For that long of a flight it is impossible to get comfortable when doing anything. Flights need to have more space and stop prioritizing costs over people.

everything was fine. but paying for 1 piece of check-in luggage and denying passengers to board with carry-on luggage which by air line's standards does not fit is not acceptable. when one travels for a longer time one needs to have some essentials

Pearson Airport could not properly handle all the passengers who they needed to process in order to properly get them on board. As a result, I missed the departure of my flight from Toronto. The only saving grace is that Air Canada found a flight that only delayed me by one hour. However, this was no thanks to Pearson Airport!

I had a good experience. I liked being informed about the status of my luggage

Everything you need to know for your flight from Boston to Winnipeg

Information on your arrival and departure airports