BOS - YWG

$132 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 1/15. 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
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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$229
Overall average: $568
Multiple Airlines
Wed 1/14Tue 1/20
BOS - YWG • 1 stop
Cheapest one-way
$132
Typical prices: $255-$375
Multiple Airlines
Thu 1/15
BOS - YWG • 2 stops
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 53% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 50% 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

Wed, Jan 14 - Tue, Jan 20
Multiple Airlines Logo
6:00 am - 3:07 pm
BOS
-
YWG
10h 07m1 stop
Multiple Airlines Logo
9:00 pm - 1:03 am
YWG
-
BOS
27h 03m2 stops
$229Multiple Airlines
Mon, Jan 12 - Sun, Jan 18
Multiple Airlines Logo
5:27 pm - 12:35 am
BOS
-
YWG
32h 08m2 stops
Multiple Airlines Logo
8:20 pm - 11:05 am
YWG
-
BOS
13h 45m1 stop
$300Multiple Airlines
Wed, Jan 14 - Tue, Jan 20
Multiple Airlines Logo
6:00 am - 3:07 pm
BOS
-
YWG
10h 07m1 stop
Multiple Airlines Logo
5:00 am - 8:30 pm
YWG
-
BOS
14h 30m1 stop
$310Multiple Airlines
Wed, Jan 14 - Tue, Jan 20
Multiple Airlines Logo
5:34 am - 12:41 am
BOS
-
YWG
20h 07m3 stops
Multiple Airlines Logo
9:00 pm - 4:19 pm
YWG
-
BOS
18h 19m3 stops
$323Multiple Airlines
Mon, Jan 12 - Sun, Jan 18
Multiple Airlines Logo
11:41 am - 5:26 pm
BOS
-
YWG
30h 45m1 stop
Multiple Airlines Logo
8:20 pm - 11:05 am
YWG
-
BOS
13h 45m1 stop
$326Multiple Airlines
Wed, Jan 14 - Tue, Jan 20
Multiple Airlines Logo
5:34 am - 11:35 am
BOS
-
YWG
31h 01m2 stops
Multiple Airlines Logo
9:00 pm - 4:19 pm
YWG
-
BOS
18h 19m3 stops
$336Multiple Airlines
Fri, Jan 16 - Sun, Jan 18
Multiple Airlines Logo
3:43 pm - 1:26 am
BOS
-
YWG
10h 43m1 stop
Multiple Airlines Logo
7:30 am - 1:13 am
YWG
-
BOS
16h 43m1 stop
$339Multiple Airlines
Fri, Jan 16 - Sun, Jan 18
Multiple Airlines Logo
3:43 pm - 1:26 am
BOS
-
YWG
10h 43m1 stop
Multiple Airlines Logo
7:30 am - 1:13 am
YWG
-
BOS
16h 43m1 stop
$346Multiple Airlines
Wed, Jan 14 - Tue, Jan 20
Multiple Airlines Logo
5:34 am - 11:35 am
BOS
-
YWG
31h 01m2 stops
Multiple Airlines Logo
5:00 am - 11:57 pm
YWG
-
BOS
17h 57m2 stops
$358Multiple Airlines
Mon, Jan 5 - Tue, Jan 13
Air Canada Logo
6:15 am - 9:44 pm
BOS
-
YWG
16h 29m1 stop
Air Canada Logo
6:00 am - 2:52 pm
YWG
-
BOS
7h 52m2 stops
$362Air 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’s the cheapest day of the week to fly from Boston to Winnipeg?

The average price of all round-trip flights from Boston to Winnipeg clicked on KAYAK for each day over the last 12 months.

For Boston to Winnipeg, Sunday is the cheapest day to fly on average and Monday is the most expensive. Flying from Winnipeg back to Boston, the best deals are generally found on Saturday, with Monday being the most expensive.

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 $642 and $568 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 53% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonApril
Cheapest flight$132
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 50% 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 $132 for a one-way ticket and $300 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 $569 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 8006 reviews
7.3Food
7.9Comfort
8.1Boarding
7.9Entertainment
8.5Crew
Airline reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

10.0 ExcellentMargaret, Dec 2025
BOS - PIT
Read more Delta reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

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.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

From the first moment you interact with United Airlines, you can expect nothing less but extreme frustration. The baggage handler at the bag drop seems completely unbothered by the presence of customers waiting in line. No help was extended to load the baggage whatsoever. And if any of your bags is overweight by 0.01 pound they will make you re-distribute everything in your suitcase just to play power trip. When it was time to board no help was extended to customers to locate their seats. Moreover. It was a chaotic mess at the gate when it was unclear who should board first and everyone just bunched up, trying to get on the plane. I am sure the crew was doing their best to perform their jobs while being paid their wages however it shouldn’t be that hard to smile once or twice when you’re in the business if serving customers. It is a shame for the United States of America to have a flagship carrier of such low caliber. Our flight was also delayed by about an hour and a half due to further delays prior to our inbound flight. Being someone who has travelled for both business and leisure in Asia, Europe, and South America I have never experienced such poor quality of service.

Nothing specific. Cabin temperature was too high for some reason.

It was just fine. I managed to make all my connection too sbut had trouble in Munich with no wheel chair and trouble trying to get help from the airport people to get to the other terminal for my flight. Finally a wonderful lady Amelia, helped me to make my flight connection Timon with zero time to spare.

Over 40 years ago my AC return flight was canceled, during this last summer the same thing happened. AC denied everything Canadian like paying for accommodations and basic necessities. So why would I ever want to fly AC again? This last flight my wife took the return flight had problems and left late, so I guess they are getting better. However I have no faith in this airline so I drove to this last destination! I'll never fly AC again!!!

Great check in process in LA and good service The check in process as well as at the gate is way better in the US versus canada 🇨🇦

Super experience. Earlier than schedule departure and arrival. Baggage handling was very good

Allow me to book extra bag check in as free though I packed in 1 luggage but that was 7 LBS overweight so make another bag to free check in.

I would like to get my money back. I flight was 4 hours late on the way to detroit, And same on my way back to Brussels they cancelled my flight and give me an other ticket and i had to wait 5 hours.

All attendents were very efficient, pleasant and happy. Everything went smoothly. The seats could have been wider. There could have been more free food instead of just one small bar.

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