BOS - YWG

$127 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 6/25. 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

Search 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

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Boston to Winnipeg.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:35 pm - 5:28 pmBOS-YWG
21h 53m2 stops
4:25 pm - 11:20 amYWG-BOS
17h 55m3 stops
Thu, Mar 6 - Tue, Mar 11
8:35 pm - 5:28 pmBOS-YWG
21h 53m2 stops
7:30 am - 9:01 pmYWG-BOS
12h 31m2 stops
Thu, Mar 6 - Tue, Mar 11
12:15 pm - 5:38 pmBOS-YWG
6h 23m1 stop
5:00 am - 11:28 amYWG-BOS
5h 28m1 stop
$301United Airlines
Find Deal
Thu, Jul 17 - Mon, Jul 21
6:00 am - 5:38 pmBOS-YWG
12h 38m2 stops
2:50 pm - 10:38 pmYWG-BOS
6h 48m1 stop
$311United Airlines
Find Deal
Thu, Jul 17 - Mon, Jul 21
2:00 pm - 10:45 amBOS-YWG
21h 45m1 stop
5:00 am - 3:30 pmYWG-BOS
9h 30m1 stop
$426Porter Airlines
Find Deal
Sat, Feb 15 - Sat, Feb 22
10:30 am - 5:18 pmBOS-YWG
7h 48m1 stop
3:00 pm - 10:39 pmYWG-BOS
6h 39m1 stop
$464Air Canada
Find Deal
Tue, Mar 4 - Sat, Mar 8
6:10 am - 1:58 pmBOS-YWG
8h 48m1 stop
7:45 am - 2:58 pmYWG-BOS
6h 13m1 stop
$478Air Canada
Find Deal
Tue, Mar 4 - Sun, Mar 9
1:00 pm - 11:38 pmBOS-YWG
11h 38m2 stops
12:53 pm - 11:50 pmYWG-BOS
9h 57m1 stop
$543Delta
Find Deal
Tue, Mar 4 - Sun, Mar 9
6:55 am - 4:43 pmBOS-YWG
10h 48m2 stops
6:40 am - 3:53 pmYWG-BOS
8h 13m2 stops
$548Delta
Find Deal
Tue, Feb 11 - Thu, Feb 20
11:05 am - 8:46 pmBOS-YWG
10h 41m2 stops
11:35 am - 10:01 pmYWG-BOS
9h 26m2 stops
$629Porter Airlines
Find Deal
Thu, Jul 17 - Mon, Jul 21

Flights from Boston to Winnipeg - Travel Insights & Trends

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 October, where tickets cost $349 (return) on average. On the other hand, the most expensive months are March and August, where the average cost of round-trip tickets is $625 and $621 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

$127
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 2% 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 $127 for a one-way ticket and $253 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 $670 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 4 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 8456 reviews
7.9Entertainment
8.0Comfort
8.5Crew
7.3Food
8.2Boarding
Airline reviews

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

10.0 ExcellentD, Jan 2025ABE - ATL
Read more Delta reviews

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

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.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Reserve check-in was very slow compared to regular check-in. Internet was slow

Lavatories broke with an hour to go. At least we were on time.

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

The additional charge for the WiFi was not worth it. Streaming a football game was a joke as it continued to lag will be requesting a refund

Long wait to check in your bag at Honolulu Airport as no kiosks therefore no bag drop line. Confusing at gate as the desk is at entrance giving the impression you need to check in there . Waited in another lineup for no reason

Flight was on time. Online check in capabilities made things quick and easy. Zone boarding was enforced, which I appreciate. Everyone was not lining up ahead of their zone being called. Crew was professional and friendly.

Flight was delayed 1.5 hours. Baggage took 45 minutes to reach carousel

more room between seats. will check out other airlines. uncomfortable - knees crammed against seat ahead

The quality of service at WestJet has really decline in the past couple years. Now they rarely leave on time and are full of excuses to obviously try to minimize their responsibility for compensation. Reality and what is mentioned at the gate for delaus rarely jive. If you apply for compensation even if appropriate, you are declined. They need to get back to doing the small things great rather than look for more reasons to grab money.

I had a guy behind me kneeing me in the back due to his limited leg room and the stewardess kindly relocated him. I was very grateful.

Everything was good till we got to yyz...then we got to the gate and there was NO GATE AGENT. We waited 15 min before disembarking. No internet No IFE Old aircraft Second leg in two weeks NOT IMPRESSED

The flight was delayed at the last moment quoting an absurd weather reason. This delay led to an issue with my connecting flight. I was made to run (literary) from this flight to the next one ( as they preponed departure. I was still in my DCA to YYZ flight when the boarding started for the next connecting flight. After my sprint to get the connecting flight, found that no place for my carry on. Had to sit for 3 hours with my back-pack on my lap , it was the most uncomfortable and inconvenient journey with little to no empathy shown by cabin crew in both flights. Another poor show from Air Canada!! Cant help because of lack of options !!

Horrible I had a health emergency and couldn’t go Air Canada refused to allow me to reschedule

First, When I check in at Phx air Canada counter, I couldn’t make it myself, either at the check in counter, the lady told me that I need a Canada visa to take this plane, then I told her that I have a lots of friends go back to China and transfer in Canada, I’ve never heard they say they needed a visa to stay in the airport, also, I have US lawful green card, as I did research, I knew all U.S. green card holders don’t need a visa to go to Canada if stay a short time. And then they agent lady asked her workmates, spent over an hour then finally have the boarding passes for me. Secondly, my flight is from Phoenix to Hongkong, one stop at Vancouver, but I had to get my bag in Vancouver then re-check in again there. I asked them, they told me that because my layover time is too long (about 20 hours), so they can’t do bags check through. I understand this, just compared with other airlines I travel before, this isn’t a good experience to me.

Excellent crew, great food despite catering issues. We need more people like this.

Very good ! I would recommande it to my friend and family

Really poor travel experience. My first flight was cancelled, which cut my international trip short and threw off my schedule. I will not be flying Air Canada again if I can so help it. The crew and in-flight experience was pleasant and enjoyable but the consistent delays and cancellations are not worth it.

I was not even asked if I want some water. Joke. Steward gave me a biscuit cover in chocolate and did not even look at me.

Economy middle seat was so narrow that I could not sit back comfortably with passengers on either side of me. Over the 9-hour flight, with my body slightly twisted most of that time, my previously-healthy left knee became very painful, even though I got up to walk multiple times. The knee is still painful 3 weeks later. Otherwise, it was a nice flight, but I was crippled over my entire vacation.

Ok Did not like that the second leg of flight was moved earlier making it a rush to make

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Morden

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.