BOS - YWG

$248 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 2/21. 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
$248
Overall average: $314
Multiple Airlines
Fri 3/6Mon 3/9
BOS - YWG • 1 stop
Cheapest one-way
$234
Typical prices: $263-$307
Air Canada
Sat 2/21
BOS - YWG • 1 stop
Top airlines
Air Canada
Cheapest • from $319 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 68% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 47% price drop
July
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

Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 3:09 pm
BOS
-
YWG
10h 09m
1 stop
Multiple Airlines Logo
9:00 pm - 11:41 am
YWG
-
BOS
13h 41m
2 stops
$248Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 3:09 pm
BOS
-
YWG
10h 09m
1 stop
Multiple Airlines Logo
8:00 am - 5:15 pm
YWG
-
BOS
32h 15m
1 stop
$278Multiple Airlines
Mon, Mar 2 - Wed, Mar 4
Air Canada Logo
5:30 am - 10:15 am
BOS
-
YWG
5h 45m
1 stop
Air Canada Logo
8:15 am - 2:52 pm
YWG
-
BOS
5h 37m
1 stop
$313Air Canada
Fri, Mar 27 - Mon, Mar 30
Air Canada Logo
5:30 am - 10:15 am
BOS
-
YWG
5h 45m
1 stop
Air Canada Logo
5:30 am - 12:14 pm
YWG
-
BOS
5h 44m
1 stop
$319Air Canada
Tue, Mar 17 - Tue, Mar 24
Delta Logo
5:50 am - 11:01 am
BOS
-
YWG
6h 11m
1 stop
Delta Logo
5:20 pm - 11:49 pm
YWG
-
BOS
5h 29m
1 stop
$322Delta
Tue, Jun 2 - Tue, Jun 9
Air Canada Logo
10:35 am - 3:04 pm
BOS
-
YWG
5h 29m
1 stop
Air Canada Logo
8:00 am - 2:47 pm
YWG
-
BOS
5h 47m
1 stop
$327Air Canada
Sun, Jun 14 - Sat, Jun 20
Air Canada Logo
5:10 am - 11:08 am
BOS
-
YWG
6h 58m
1 stop
Air Canada Logo
7:55 am - 2:41 pm
YWG
-
BOS
5h 46m
1 stop
$331Air Canada
Mon, Mar 2 - Wed, Mar 4
Air Canada Logo
3:35 pm - 11:54 pm
BOS
-
YWG
9h 19m
2 stops
Air Canada Logo
6:00 am - 2:52 pm
YWG
-
BOS
7h 52m
2 stops
$332Air Canada
Sun, Jun 14 - Sat, Jun 20
Air Canada Logo
5:10 am - 10:03 am
BOS
-
YWG
5h 53m
1 stop
Air Canada Logo
5:10 am - 2:41 pm
YWG
-
BOS
8h 31m
2 stops
$345Air Canada
Mon, Mar 2 - Wed, Mar 4
Air Canada Logo
6:40 pm - 10:15 am
BOS
-
YWG
16h 35m
1 stop
Air Canada Logo
6:00 am - 2:52 pm
YWG
-
BOS
7h 52m
2 stops
$349Air 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 July, where tickets cost $233 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $622 and $580 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 68% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonMarch
Cheapest flight$234
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 47% 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 $248 for a round-trip ticket.

  • 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 $586 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 8128 reviews
8.5Crew
8.1Boarding
7.8Entertainment
7.9Comfort
7.2Food
Airline reviews

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

2.0 MediocreAlparda, Feb 2026
BOS - ICN
Read more Delta reviews

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

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.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

Flight was good but there are way to many announcements for credit cards etc.

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

Was delayed at every point/ connection. Luggages missing for 5days. Had no medications for diabetes and high B/p. when bags where finally delivered on the 30th, the insulin and ozempic were no longer patent, as the ice pack had since dissolved and the authenticity of the med is now questionable, since they must be refrigerated. Please have them refund my bag fees. I should sue them for all the inconveniences caused to me.

The plane was delayed substantially due to a mechanical problem, that being said, the airline was very fair with providing a meal coupon for us. I would rather arrive late on a mechanically sound plane than the alternative. The food served in the plane was just awful, however and I recommend a new catering company.

I waiting for 2 hrs to retrieve my luggage. Didn't get home till 3am.

The flight left late and I didn’t get a glass of bubbly upon boarding (which I’m used to when booking business class on other flights), but otherwise it was a pleasant flight with lovely, helpful crew members and I enjoyed my meal.

Flight cancellations, delays, mass confusion and disorganization! That’s Air Canada for you, nothing new. I would have chosen a different airline if it were an option, and Air Canada continues to prove they don’t care about their customers.

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

Couldn't fit knees, only 1 toilet working, didn't get anything to drink cause the stewards were not able to get to us

Flight was canceled for a reason they knew hours before but did not mention. Next the gate chnage from 37 to 38 at least 10 times. Ridiculous.

The flight from SFO to YVR was delayed and my bag did not make it to my next flight from YVR to SYD. It took almost 3 days after I landed to get my bag and when I got it, it was filled with dust

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!

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

Information on your arrival and departure airports