BOS - YWG

$96 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 3/31. 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
5:10 am - 3:08 pmBOS-YWG
10h 58m1 stop
8:25 pm - 5:14 pmYWG-BOS
19h 49m2 stops
Fri, Mar 28 - Thu, Apr 3
6:00 am - 4:28 pmBOS-YWG
11h 28m1 stop
6:30 am - 10:12 pmYWG-BOS
14h 42m2 stops
Fri, May 30 - Mon, Jun 2
6:00 am - 4:28 pmBOS-YWG
11h 28m1 stop
9:00 am - 10:12 pmYWG-BOS
12h 12m1 stop
Fri, May 30 - Mon, Jun 2
6:13 pm - 3:08 pmBOS-YWG
21h 55m1 stop
5:00 am - 9:52 pmYWG-BOS
15h 52m2 stops
Sat, Mar 22 - Thu, Mar 27
8:20 pm - 1:09 pmBOS-YWG
17h 49m2 stops
7:00 am - 7:35 pmYWG-BOS
11h 35m1 stop
$328United Airlines
Find Deal
Mon, Jun 9 - Sat, Jun 14
6:00 am - 5:38 pmBOS-YWG
12h 38m1 stop
5:00 am - 11:28 amYWG-BOS
5h 28m1 stop
$339Air Canada
Find Deal
Mon, Aug 18 - Sun, Aug 24
8:20 pm - 1:03 pmBOS-YWG
17h 43m2 stops
6:35 pm - 11:28 amYWG-BOS
15h 53m1 stop
$353United Airlines
Find Deal
Mon, Aug 18 - Sun, Aug 24
9:45 am - 6:00 pmBOS-YWG
9h 15m2 stops
11:45 am - 10:01 pmYWG-BOS
9h 16m2 stops
$395Porter Airlines
Find Deal
Fri, May 30 - Mon, Jun 2
3:15 pm - 11:29 pmBOS-YWG
9h 14m1 stop
5:43 pm - 11:50 pmYWG-BOS
5h 07m1 stop
$406Delta
Find Deal
Sat, Mar 22 - Thu, Mar 27
7:05 am - 5:59 pmBOS-YWG
11h 54m2 stops
11:35 am - 5:50 pmYWG-BOS
5h 15m1 stop
$487Porter Airlines
Find Deal
Thu, Apr 17 - Thu, Apr 24

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 January, where tickets cost $341 (return) on average. On the other hand, the most expensive months are March and February, where the average cost of round-trip tickets is $642 and $624 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 7 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

July

Cheapest flight

$96
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly and prices are also 8% 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 $96 for a one-way ticket and $270 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 $676 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 8061 reviews
7.3Food
8.0Comfort
8.5Crew
8.2Boarding
7.9Entertainment
Airline reviews

Delta is a premier airline so my expectations are most always met.

10.0 ExcellentGreg, Mar 2025PHX - MSP
Read more Delta reviews

Delta is a premier airline so my expectations are most always met.

Seats are much much more comfortable than United, which is what I usually fly

Zero updates from the pilots for 30 minutes in the tarmac

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Rode in a smaller plane and short trip meant no snacks, no free wifi or tv. It was only 30min flight so honestly wasn’t a big deal to lack these items.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

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.

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

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

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

All was good with comfort and ease of boarding. There was confusion from what gate to board at. Meant moving a long distance but I allowed plenty of time for this.

Terrible experience. Flight was delayed then canceled. They had no clue how to rebook us. Had to wait in line to take to a gate agent for 2 hours. Absolutely terrible from start to finish.

We have to wait long time at airport. Plane left from 8 pm to 1:35 am.Long time waiting

My oroginal flight was delayed several times. Finally the flight was cancelled. I had to spend additional money and book another flight with Porter at another airport Fort Lauderdale International Airport or I would miss the event I had in Toronto. I did not board the rescheduled flight which was after my event.

The staff could have been friendlier. And Having the flight on time would have been much more convenient.

Excellent We were very empress with this Airline as once our flight was canceled, they immediately rebooked our flight and provided accommodations for hotels….Thank you!

Awful. Flight screen didn’t work. Seat didn’t recline.

I liked nothing about this flight nor the incredible lack of service and communication on this flight from the Captain to every staff member. Arrogant, entitled and lacking any kind of basic customer service

Everything should be better, terrible flight and airport service. Delayed for 6 hours, flying around for 1 hr, and keeping us on a plane for another 2,5 -3hrs.

The plane was dirty. It appeared that Air Canada did not know vacuum cleaners had been invented. Second, the overhead bins were about 1/3 or 1/2 the size of "normal" bins. That was a problem. The worst was disembarking in the weather in Montreal. I have cold agglutinin disease. That means my red blood cells clump together and then are destroyed when exposed, even by breathing to cold air. A few seconds of exposure can be dangerous. I am now experiencing extreme fatigue caused by the anemia from that experience. I should have had more assistance descending a narrow ramp and then traversing, even if only a few feet, of icy pavement. The blowing snow penetrated my facial covering and has caused problems.

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.