BOS - YWG

$119 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 5/2. 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

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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Cheap Flight Deals 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.

Recent round-trip flight deals from Boston to Winnipeg

KAYAK's recommended round-trip deals from the most popular airlines that fly from Boston to Winnipeg.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Air Canada Logo
10:20 am - 3:00 pmBOS-YWG
5h 40m1 stop
Air Canada Logo
5:00 am - 11:28 amYWG-BOS
5h 28m1 stop
$291Air Canada
Find Deal
Fri, May 2 - Fri, May 9
Air Canada Logo
12:15 pm - 5:38 pmBOS-YWG
6h 23m1 stop
Air Canada Logo
6:35 pm - 11:28 amYWG-BOS
15h 53m1 stop
$295Air Canada
Find Deal
Fri, Jul 4 - Sun, Jul 6
United Airlines Logo
7:00 am - 4:12 pmBOS-YWG
10h 12m2 stops
United Airlines Logo
5:00 am - 11:28 amYWG-BOS
5h 28m1 stop
$307United Airlines
Find Deal
Mon, Jun 9 - Sun, Jun 15
United Airlines Logo
8:25 pm - 1:09 pmBOS-YWG
17h 44m1 stop
United Airlines Logo
4:25 pm - 8:56 amYWG-BOS
15h 31m2 stops
$309United Airlines
Find Deal
Fri, May 2 - Fri, May 9
Delta Logo
8:25 am - 8:08 pmBOS-YWG
12h 43m2 stops
Delta Logo
12:52 pm - 10:56 pmYWG-BOS
9h 04m2 stops
$314Delta
Find Deal
Sat, May 17 - Sat, May 24
 Logo
8:59 am - 5:41 pmBOS-YWG
33h 42m3 stops
 Logo
9:00 am - 2:55 pmYWG-BOS
28h 55m1 stop
Fri, May 2 - Mon, May 5
 Logo
6:00 am - 4:23 pmBOS-YWG
11h 23m1 stop
 Logo
6:30 am - 10:12 pmYWG-BOS
14h 42m2 stops
Thu, Jul 17 - Sat, Jul 26
Porter Airlines Logo
3:50 pm - 10:46 pmBOS-YWG
7h 56m1 stop
Porter Airlines Logo
11:45 am - 6:08 pmYWG-BOS
5h 23m1 stop
$411Porter Airlines
Find Deal
Thu, Jul 31 - Sat, Aug 9
Porter Airlines Logo
8:45 am - 6:00 pmBOS-YWG
10h 15m2 stops
Porter Airlines Logo
11:45 am - 9:31 pmYWG-BOS
8h 46m2 stops
$423Porter Airlines
Find Deal
Mon, Jun 9 - Sun, Jun 15
Delta Logo
5:20 am - 4:45 pmBOS-YWG
12h 25m2 stops
Delta Logo
8:30 am - 10:33 pmYWG-BOS
13h 03m2 stops
$531Delta
Find Deal
Mon, May 19 - Sun, May 25

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 January, where tickets cost $341 (return) on average. On the other hand, the most expensive months are April and March, where the average cost of round-trip tickets is $770 and $643 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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low season

February

High season

December

Cheapest flight

$119
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly with an average 1% increase in price.
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 $119 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?

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

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

    The two airlines most popular with KAYAK users for flights from Boston to Winnipeg are Delta and Porter Airlines. With an average price for the route of $694 and an overall rating of 8.0, Delta is the most popular choice. Porter Airlines is also a great choice for the route, with an average price of $421 and an overall rating of 7.9.

  • 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.

See more FAQs

Top 5 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.
8.0
DeltaOverall score based on 7897 reviews
8.5Crew
7.3Food
7.9Entertainment
8.2Boarding
8.0Comfort
Airline reviews

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

10.0 ExcellentSunderesh, Mar 2025AUS - BOS
Read more Delta reviews

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

After a 5 hour delay waiting at the gate (3 delays adding up) with no clear reason provided, we finally boarded flew 3/4 of the way to Toronto then were turned back to New York. As we neared New York, the pilot declared that it was his fault, something to do with timing and him not being allowed into the country???? How could the airline let his happen? They had hours to prepare and make sure they had a crew available for the flight! We ended up in Toronto a day late with no sleep.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Friendly flight attendants, smooth 8-9 hours flight. Economy seats are small and uncomfortable as usual.

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Bathrooms dirty sinks clogged. No one seemed to clean them. Plane very old

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

The gate was too far away for the connecting flight

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

Compared with other carriers business class for an overnight was not worth the extra expense.

Seats were comfortable. It’s was so cold and very uncomfortable. I paid 2000 miles for wifi service that was choppy the whole flight. Would like to be reimbursed for my miles Food was so disappointing. Three cold and terrible meals for $3000 round trip. This needs to be better.

Generally good. The aisles have gotten narrower which can slow down boarding. Flight crew was great! Healthier complimentary snacks would be appreciated. Due to earthquake in San Francisco we had to circle in air space for a bit but then had a smooth landing. I laud the flight crew for their patience ;)

Easy to board. Flight was super crowded though so I didn't sleep well on that cross country red-eye flight. The aisles seem ot have gotten narrower and the seat smaller whn luggage and people are getting bigger so it would be AWESOME to have more space and breathing room in general ;)

We were delayed in Toronto on the tarmac for THREE hours with no clear indication as to why except that it was not a safety hazard. Pilot did apologize more than once but even he was unable to explain why exactly we were delayed. I overheard the stewards saying that the captain was very frustrated with the situation as well because he was not able to explain why except it had something to do with water supply or system on the aircraft and now we needed to wait for an engineer to approve the aircraft for flight. It was very frustrating and distressing as a passenger and we should have been given complimentary meals at the very least.

All male crew was just too woke for me. I felt like a sardine. I will never take a window seat or the rearmost seat again. I booked early and did not pay for seat selection and that was a mistake. The security at IAH was atrocious. I was violated and radiated as I was in a hurry to connect to my other flight. I may have lost items under the seat in front of me that I couldn't see nor bend over to look.

Liked nothing. As per previous segment it was delay delay delay.

In general ok, my only issue is that they had no hot items for purchase. I had very little time in my connection due to baggage/customs/TSA, thag I barely even had a chance for a stop at the washroom and buy water, to make it to my gate when they started boarding. I had nothing to eat because the trip started early, so I was ready to purchase, and they had nothing except for dry items like snacks. I had to purchase a mediocre, overpriced cheese and fruit board, instead of at least a pizza or sliders that I was planning on getting. Other than that, it was fine. But that’s typical Air Canada, to not have enough.

Flight was delayed 3 times. Then cancelled due to pilot being timed out. They refused hotel vouchers. Gate attendants were very rude and could not help you at all.

Good. Would be better if the carry on baggage was free.

Horrible. I checked out myself that it seems that I can have a free carry-on. But they ask me to pay $75 when we are nearly boarding. It was tricky during check out that make you mistake that you can have a carry-on beside your personal item. Also they ask $75 in the airport instead of $35 during checkout. So the whole process is designed to make you this mistake

Westjet is one of the worst airlines in the world. 100% guaranteed to have flight delays and flight cancellations. Will never book again with Westjet.

Plane should have entertainment, instead of people paying to use wifi

Westjet has been absolutely terrible! Flights continually cancelled. Took 4 days to get home. Would have been 5, but we booked last flight with another airline after our Westjet flight was cancelled. Even pilot on original flight looked frustrated! Funny how they say cancelation is weather related, but they still have more than 1 other flight leaving to same destination on same day, but of course those are all full. This happened more than once on this trip. Two weather related cancelations and 1 mechanical. Not sure if the last flight even went ahead. Felt so sorry for families with kids and babies, and the older travellers. Felt like we lived out of suitcases and airports for days - SO RIDICULOUS! Next to no help from Westjet staff at airports, but it appears there is nothing they can help you with. Westjet has made it that they are unreachable when you need them! People were getting extremely frustrated, and rightfully so. Additional costs to us really added up, but Westjet literally DOESN'T CARE! Final straw was when we had to pay $1280 on a different airline (economy) trying to get home after another cancelled flight. Westjet will be refunding us a whole $140! Can't believe how this airline operates. We will never, ever use them again!

The only thing I didn’t like was how far away the gate was. I would have requested a wheelchair had I known.

no staff available to help, no systems available to coordinate

Flight was delayed. Arrived in Vancouver at 3 am. Not a great experience.

Scrooge airlines spoiled my last chance at Christmas with my 95 and 92 year old folks. and rest of the family in Calgary. Ticket personnel would not let me on without a passport and I always visit Canada with my enhanced driver;s License when I travel from the US

it was red eye flight, it was ok, there was beverage service, thats it i didnt care much as i wanted to sleep

1. Nowhere to sit at the gate D4 2. No control of lining up in different zones 3. People pushing in during the line up of zones. 4. Certainly not in a dignified manner.

Everything went smoothly. I appreciate the selection of free movies.

I like the friendliness of the crew members. I think the snack could’ve been better instead of a small package of pretzel. I like that they offer me something to drink.

The TSA agents in Phoenix were incredibly rude and confiscated belongings that we wanted to check. The flight got changed without our knowledge to a worse situation. The whole thing was terrible

Air Canada was great! From the airport at Montreal to boarding to the food on board the plane. The crew was great too! There was a slight issue with some other peoples’ tickets that I overheard about but the crew handled with care immediately to ensure everyone was comfortable and we could takeoff! Great experience with Air Canada

My experience with Air Canada was good. Great customer service… only a few delays and issues with the tunnel to exit the plain. I did not appreciate that we arrived at terminal D and had to go to terminal E to get the bags/ luggage.

PDX staff was great and we arrived on time in YVR.

They announced before boarding that the flight was full and there would be limited space in the overhead bins and you could check in for free. We did and after we boarded the plane found it was not full and there was plenty of space in the overhead bins. I’m not sure why they made this announcement.

Front desk attendant wouldn’t check me in even though there was not a single person in line. Made me use the kiosk. Kiosk had an error (of course) no baggage can be checked at this kiosk please see attendant. Then I had to wait in line for the same front desk attendant waiting for 5 people who ended up coming in front of me while I tried to use a broken and useless kiosk. Finally after checked in, wait 30 min to board all the way to zone 6 and they would deny me even after all the zone 1-5 people already went. Just literally making us wait to board so they stand there doing nothing for 5 minutes. Just ridiculous and awful customer service. Fly with literally anyone else

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

Information on your arrival and departure airports

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